Ridgefield Place Names beginning with O

Entire contents copyrighted 2005 by Jack Sanders. 
Reproduction without permission is forbidden.

Oak Tree Lane, a road so small it doesn't show up on many modern maps, is a dead-end lane off Route 7 between Wilridge Road and Old Town Road in Branchville.
The road and lots along it are shown on a 1940 map filed with the town clerk by the developer, Joseph L. Dioguardi. The road name does not appear until a 1950 map, called "Revised map of Pine Tree Lots, owned by Joseph L. Dioguardi, Branchville District."
The road was apparently so called because a huge oak tree, said to have been the largest of its genus in the Georgetown area, was situated along the road. The four-foot diameter, 150-year-old tree on the property of Mr. and Mrs. Edward and Myrna Byron was felled in July 1979 after it was determined to be a hazard because of rot.
There are more than 20 species of oaks, most of them native to our area. Among the most famous American tree genera, oaks provide about half the annual production of hardwood lumber in this country. Most older houses in this area were framed with oak while today, cheaper, faster-growing softwoods are used for construction. Much furniture, particularly Victorian, was made of oak. Nowadays, because supplies don't meet the demand and because of its higher cost, oak is found mostly in small-piece, glued-up floorboards and in some furniture.
Acorns, the fruit of the oak, are one of the most popular products of nature for wildlife. Most herbivorous mammals enjoy dining on them. It is also a main dish of the wild turkey, which has been increasing in numbers as our oak woods expand and numbers of acorns increase.
While this is our only oak place name, the tree has lent its name to many hundreds of localities across the country. Oak Grove is one of the top five most commonplace names in the United States - there are at least 91 communities so called, including seven in Alabama and 12 in Tennessee!

The Oblong is a term applied to a one and three-quarter mile wide strip of land along the western border of Connecticut from the Massachusetts line to the north border of New Canaan. This land was deeded by Connecticut to New York in 1731 in exchange for Greenwich and other land, essentially ending a long dispute about the location of the western border of Connecticut.
As a consequence of this trade, much of early Ridgefield is now in New York State. Within the town of Lewisboro, the Oblong includes the village of South Salem and virtually all the territory south to (but not including) Vista, and west to Cross Pond (Lake Kitchawan), plus the east half of Lake Waccabuc.
In North Salem, the village of that town, plus half of Peach Lake would probably be in Ridgefield today, were it not for the Oblong separation. That's quite a chunk of territory, and Ridgefield's loss of it did not please the Proprietors, the first settlers, who had purchased this land from the Indians and had led its settlement.
Ridgefield wanted compensation for its loss, which included rolling hills used for wheat and other crops, and the hilly western slopes of West Mountain, a source of timber. So the General Assembly granted the town a large wedge of territory north of and including part of today's Ridgebury. This grant encompassed the western section of modern-day Danbury all the way to New Fairfield. (The northern part of Ridgebury, now the western part of Danbury, was ceded to Danbury in 1846 - see Ridgebury.)
The Oblong is a term that refers to the shape of the ceded territory. By definition, an oblong is a rectangle that has one dimension - length or width - larger than the other. The ceded land certainly qualified in that respect. It's less than two miles wide and 50 miles long.
The western line of Connecticut was a matter of debate and disagreement long before 1731. In the early 1600s, the Dutch laid claim to all the land west of the Connecticut River as part of New Amsterdam. Nonetheless, English colonists bought lands from the Indians and settled the coastal territories as far west as present-day Rye, N.Y.
In 1654, representatives of the Dutch and English colonists agreed that the boundary should run from a line beginning at Greenwich Bay and extending 20 miles north. In addition, Connecticut received all of Long Island, east of Oyster Bay.
However, in 1664, the British took over New Amsterdam and called the colony New York after James, the Duke of York, who received the land by royal charter. In the same year, the two colonies agreed that the boundary should be generally 20 miles east of the Hudson River, although Connecticut was to have land along the coast that was west of the 20-mile line.
New York eventually decided that the agreement gave Connecticut coastal territory too far west, so in 1683, another conference took place. There it was agreed that Connecticut could retain or obtain title to Greenwich, parts of Stamford, Darien, and New Canaan. The size of all the Connecticut territory west of the 20-mile line was calculated at about 62,000 acres. To compensate New York for this "loss" of land to which it had at times claimed title, Connecticut agreed to give up land along its western border - one and three-quarters miles and 20 rods wide. From the Wilton-New Canaan corner north to Massachusetts, this oblong amounted to 61,440 acres. Hence, the Oblong was also called "The Equivalent" and the new Connecticut border was sometimes called the Equivalency Line. In the exchange, Connecticut also gave up claims to Rye and Bedford, N.Y.
Discussions continued until 1731 when the agreement was completed and money was available to survey the boundaries. Thus, Ridgefielders who had bought and settled lands that were all within the Oblong were not caught unaware that their home state might change. An example of this foreknowledge is Joseph Hobart's deed to Mathew Seamore five acres at the Southwest Ridges in 1728. Hobart stipulated that "it is also to be understood that if ye dividing line of ye Governments take ye same (five acres) into York government, that I defend it not unto him, or make it good, but only give him up all my right and interest in ye grant of said lands upon him."
The ceding of land caused some problems with titles, although it appears that most Connecticut people who suddenly became New Yorkers held on to the land they had obtained through deeds filed in Connecticut. Consider, however, the concern of Timothy Canfield, who filed the following statement in the Ridgefield land records in 1739. Mr. Canfield described himself as "living in ye Oblong near Ridgefield, in ye county of West Chester and Government of New York, having formerly purchased six acres of land of James Northrup of Ridgefield ... which land lyes in ye Southwest Ridges so called ... which tract of land was cutt off by ye Government line, whereby my title and property unto said land utterly passed and became void..." Later, however, he indicates that he still had title to the land.
Although the 1731 boundary was official, Connecticut remained dissatisfied with the line, maintaining in 1855 that boundary markers had disappeared or were unclear. A new survey was undertaken that year, but it wasn't until the 1880-81 sessions of the New York and Connecticut legislatures that the line was ratified and that Congress confirmed it - 235 years after the discussions began.
The term, the Oblong, appears in the Ridgefield land records as late as 1786, but lasted years longer in New York State towns.

Olcott Way is one of several private roads at Casagmo (q.v.), the condominium development on northern Main Street.
Casagmo's developer, David L. Paul, chose the name to commemorate the family of George M. Olcott, whose initials form the last three letters of "Casagmo." "Casa" means "house" and the Olcotts' large Italianate house stood on the site from the 1890s until, decaying and vandalized, it was razed in 1968.
George Mann Olcott, son of Charles Mann and Maria Cornell Underhill Olcott, was born on Aug. 23, 1835, in Brooklyn, N.Y., and attended Columbia College Grammar School.
"However," wrote his daughter, Mary, in a family history, "a youthful delight in caricature terminated his school life, for the headmaster ... failed to appreciate a portrait of himself done by the young Mr. Olcott, and a caning was ordered. The boy's father gave him his choice, either to undergo the caning or leave school. George M. Olcott left school and entered the world of business, where he achieved notable success."
At age 16, Mr. Olcott was a clerk in a wholesale drug firm. By 21, he was a partner in a drug importing company, later called Dodge and Olcott, of which he became president in 1904. He gave up the post when he went blind at the age of 78.
Mr. Olcott was a founder and president of the First National Bank of Ridgefield (which later merged with Union Trust Company), and was a vice president of an insurance company.
On July 30, 1892, Mr. Olcott bought from Squire Benjamin Stebbins the old Stebbins homestead, whose saltbox house had stood on northern Main Street from the early 1700s and which served as a hospital during the Battle of Ridgefield. He tore down the house and in 1893, built his own place, Casagmo.
"Mr. Olcott's heroic acceptance of his blindness increased the love and esteem in which he was universally held," his daughter wrote. "A serene philosophy of life, an upright and self-sustaining quality was his greatest strength."
He died Sept. 14, 1917 at Casagmo.
Mr. Olcott married Jennie Arnold in 1858 and they had three children, including Mary Louisa Beatrice Olcott, who was born in 1864 and who lived at Casagmo until her death in 1962 at the age of 97. Miss Olcott published Poems in 1902 and also wrote articles on gardens and flowers. She was active in the Ridgefield Library, woman's suffrage, served on many woman's rights committees, and often spoke at meetings. Her other interests included gardening and breeding prize poodles, game birds and swans, all at Casagmo.

Old Barlow Mountain Road is a section of Barlow Mountain Road that is now either little-used or abandoned. Today, the name is used chiefly for a short, dead-end road near the intersection of Knollwood Drive and Barlow Mountain Road.
As noted under Barlow Mountain Road, today's "old" road is a portion of the original Barlow Mountain Road, which included the modern road from North Salem Road, past Pierrepont Pond, to a point where it continued over a now-abandoned path to today's Old Barlow Mountain Road. From there the road went into Pierrepont State Park where its route through the woods, still clearly visible, is used as a walking trail. It comes out of the park along a residential driveway to Limestone Road.
Barlow Mountain Road was named for blacksmith John Barlow whose shop and farm was along the road in what is now parkland. Remnants and foundations can still be seen, and 20 years ago at least, an explorer could find various pieces of farm hardware lying around the old farmyard.
The path was an old stagecoach road and may have been a route used by American troops on their way to the battle of Ridgefield in April 1777.
In this history, this is the first of about two dozen road names, some no longer in use, that begin with the word "old." Frequently, the word is employed to indicate a road that has been replaced by a more modern highway. Sometimes, however, it refers to a former use of the road or some facility along the road, or is just a quaint addition to a pre-existing name.

Old Branchville Road is another highway whose "old" refers to its replacement as a main road by a newer road. In this case, the newer road is a section of modern-day Branchville Road, Route 102, that was built in 1851 to improve wagon transportation to and from the new train depot at what we now call Branchville.
The Danbury and Norwalk Rail Road had run its line through in 1850. Old Branchville Road, part of the old route from the village to the new station, was too hilly and, in places, too swampy, for reliable year-round transportation, especially when heavy freight wagons carrying such cargo as coal and lumber, were running between the station and the village.
Old Branchville Road is a very old highway, laid out by the "Select Men" on Dec. 26, 1744. They described the path from its start as "beginning at Fairfield (now Redding) line at ye south end of Cedar Mountain at ye northeast corner of Abraham Bennit's land, and so running westward between ye Bennit's land and Matthew Seamore's till it come to ye west side of ye land at ye Wolfpitts, and from thence westward 8 rodds wide till it comes to ye Pompion Ridge to Smith's lott and Osburn's, and thence onward as ye way is now to town..."
Pompion or Pumpkin Ridge is the hill at the top of Branchville Road, just west of the Old Branchville Road-Branchville Road intersection.
Until fairly recently, Old Branchville Road was a dirt lane, in poor condition. Earlier in the century, much of the property along it belonged to the estate of Herbert Spencer Grimes, and there were few houses along it.
Among the landmarks on the road is the Branchville Schoolhouse, an early 20th Century structure.

The Old Burying Ground, mentioned as such in 19th Century deeds, was the town's first cemetery. It stands on Wilton Road East below Main Street and just north of Creamery Lane.
The cemetery was laid out in the year of the town's founding and is marked today with a monument, inscribed: "Ye burying yard lay'd out ye Nov. 25, 1708, by ye first settlers of the Town of Ridgefield."
The marker lists 40 pioneers buried there as well as "an unknown British soldier killed in the Battle of Ridgefield." The Village Improvement Society erected the monument in 1931 after time and vandals had destroyed most of the old headstones.
When he was writing his history of Ridgefield in the 1920s, George L. Rockwell found only two tombstones still standing in the Old Burying Ground. Today, nothing remains except a small portion of a slate stone, lying flat on the ground, which says "54th year of his age" and which probably belonged to the grave of Captain Matthew Benedict "who departed this life July 7, 1757," according to town records. Capt. Benedict, born five years before the town was settled, probably came as a small child.
The cemetery was probably abandoned sometime around the Revolution in favor of the Titicus Cemetery, which began to be used around 1735. Why the change was made is unclear. It may have been that land for expansion was unavailable or that Titicus was more centrally located and convenient.

Old Church Road is a name that was hand-written on a 1935 assessor's map in the town hall for a road that was on the east side of a triangle of land, on which stood the Episcopal Church of Ridgebury. The road ran from Ned's Mountain Road northwesterly to Ridgebury Road, and may now be part of a private driveway that still exists in this vicinity.
Ridgebury had been a mission of the Episcopal Church by 1731, the year Ridgebury was patented, although very few people were living in upper Ridgebury then. A church building was probably erected between 1750 and 1760 and remained in operation with visiting ministers until the outbreak of the Revolution, when the Church of England became unpopular. After the war, in 1789, the Ridgebury church was reopened by the minister from Ridgefield, Dr. David Perry, but a year later, was abandoned. The church building was razed in 1810.
An Episcopal cemetery stood near the church within the triangle. Sometime during the 19th Century, it was said, many of the stones were removed by someone - obviously neither religious nor afraid of ghosts - and used for fill around the foundation of a house built at the north tip of the triangle. A few stones were left standing into the 20th Century, but they and their graves were eventually removed to another cemetery.

The minutes of the Annual Town Meeting of 1911 mention "the Old Creamery Highway," perhaps the earliest name for what we today call Creamery Lane, the short road that runs between Wilton Roads East and West, just below Main Street.
The road was named for a creamery - a place where butter was produced - that was established on the north side of the street near Wilton Road East. It began operation in March 1889 and by its fifth year was producing 60,000 pounds of butter (14,000 more pounds than the year before). At 27 cents a pound, sales of the butter totalled $16,402, earning dairy farmers $13,375 for the milk and cream they supplied.
Officers of the Ridgefield Creamery were well-known Ridgefield farmers of the day: J. W. Rockwell, John F. Holmes, William A. Benedict, R. W. Keeler, Ebenezer W. Keeler, A. C. Keeler, J. A. Wakeman, and H. A. Barrett.
The building occupied by the creamery is now three stories of apartments. For many years, the Goodwill Baptist Church, the town's only black congregation, worshipped there, a fact noted on a historical marker on the building.
Tradition has it that the structure was once the First Congregational Church, a typically New England-style frame structure that stood on a green on Main Street at the head of Branchville Road. That church building's doors were closed in 1888 when the existing stone church was opened at Main Street and West Lane, and it's perhaps no coincidence that the creamery opened in early 1889.
The fact that the Town Meeting spoke of "Old" Creamery Highway suggests that the creamery was no longer in use; there was no reason to label the highway itself old.
The term "highway," incidentally, tends to convey the image of a major thoroughfare. However, in pre-pavement days, just about any public road could be called a highway.

Old Danbury Road is the name of the short stretch of highway, just east of Danbury Road, that runs between Haviland and Danbury Roads. It forms the east side of a triangle, and connects to Danbury Road opposite the Limestone gasoline station.
This was the original beginning of the Danbury and Ridgefield Turnpike, which ran from Haviland Road north through Sugar Hollow to Danbury. The turnpike was incorporated in 1801 and built shortly thereafter.
Around 1928, Old Danbury Road was bypassed by the straighter stretch of Danbury Road, which was by then a free state highway.

Old Farm Road is a paper highway, having appeared as the main road on a 1957 subdivision map filed by Herman J. Leffert and others. The 100-acre parcel was called Rolling Meadow Estates. The neighborhood, now called Ridgebury Estates, is situated between Briar Ridge and Shadow Lake Roads.
The Leffert subdivision was never developed. Other roads shown on the map are Pasture Lane, Pheasant Lane, Hawk Court, Little Brook Lane, Dairy Court, and Dairy Drive. Although the road was never built, the name of Old Farm Road still appears on some maps and in some records in the town hall.

Several deeds in the 1830s refer to the Old Hill, a locality that seemed to be near Lake Mamanasco. The name was probably derived from Old Hill Lot - a term in which the "old" modifies "lot." To say that a hill is old is stating the obvious and would not be typical of 18th or 19th Century names.

Old Main Highway is a quaint and accurate name for the road east of and parallel to the railroad tracks and Route 7 in Branchville.
Years ago - at least before 1920 - the Sugar Hollow Turnpike, the highway that is now Route 7, ran on the east side of the tracks in Branchville until several hundred yards north of the train station. Hence this road was part of the "main highway."
The roadway was moved to the west side of the tracks, probably to avoid two crossings over the tracks and over the Norwalk River.
The 1934 assessors' maps call this road "Old Norwalk Road." Modern maps frequently call it West Branchville Road (q.v.), one of the most ludicrous of Ridgefield's road names since the road is in the easternmost part of Branchville and the town.

Two deeds in the 1850s mention the "Old Meeting House Tract," a term that referred to a parcel on the corner of North Salem Road and North Street.
It was on this plot that the first church building of the Methodist Society was erected in 1824. The structure was used as a church until 1841 when a new Methodist church was erected at the north corner of Main and Catoonah Streets, a site that remained the location of the Methodist church here for more than a century. In the mid-1960s, it was razed and replaced with a brick office-store building when a new church was opened at Main Street and King Lane.
After the first church was vacated, the property was sold to private owners - probably Jared Mead and Lewis Slauson - who converted it into a house. Eventually, the tract became part of the Ridgefield Cemetery, and the Lounsbury family plot today occupies the exact spot where the church stood.

The Old Horse Pound, discussed in more detail under Horse Pound Swamp, was a term that appeared in a 1796 deed for six acres "on the Mountain near the Old Horse Pound."
The horse pound, presumably used to contain stray horses, was established in 1717 somewhere in the southwestern part of town, probably in the vicinity of West Lane or South Salem Road, perhaps near the state line.
The fact that it was called "old" in 1796 suggests that it had not been used in some time.

Old Mill Pond was the named used by Otto H. Lippolt on the map of his 1959 Hemlock Hills subdivision for a small body of water on the west side of Old Mill Road.
The name suggests that there was a mill, undoubtedly a saw mill, connected with the pond some years ago. It may not have been a very old mill, for no mention of a saw mill in this neighborhood was found in an inspection of all the town's land records before 1880. 
The pond has also been called Lippolt Pond.

Old Mill Road runs from George Washington Highway to Ned's Mountain Road, past the Old Mill Pond. It is the main road of Otto Lippolt's Hemlock Hills subdivision, and was developed in the early 1960s.

Old Musket Lane is a short, dead-end road of Powderhorn Drive. Both roads are part of a subdivision, called Gun Hill Farms, the initial work on which was done by Donald Thomas, but which was named and developed by Robert E. Roche.
Mr. Roche was interested in guns and things Western, and selected these colonial-sounding firearms names.
The subdivision existed by late 1964 when development began. Old Musket Lane was probably built around 1965; it became a town road in 1970.

Old Nod Road is another name for Old Branchville Road, according to a deed filed with the town clerk in 1946.
Old Branchville Road connects to Nod Hill Road, which leads up Nod Hill and into Wilton where the road is also called Nod Hill Road.
Old Branchville Road was the original route of a highway from the village to the southeast corner of town. Before Branchville as a community came into being with the arrival of the railroad around 1850, today's Old Branchville Road may have been more commonly thought of as a route to Nod Hill and may have been called the Road to Nod Hill - shorted to Nod Road.
However, today the road is called Old Branchville because it was the original route of the road from the village to Branchville. It was less used after the new, less-hilly route after the railroad arrived.

Old Norwalk Road is another name for Old Main Road, the narrow highway that parallels Route 7, east of the railroad tracks in Branchville, and that is foolishly also called West Branchville Road. This road was the original path of Route 7 in this vicinity and, to people to the north, like Danburians, it was the Norwalk Road. It was also often called the Danbury-Norwalk Road or Turnpike.

Old Oscaleta Road is the name applied to the short, old section of the west end of West Mountain Road into New York State. As the name suggests, the road was once the western extension of Oscaleta Road.
Before the new section of West Mountain Road was built west of Old West Mountain Road, Oscaleta Road served as the main road over the mountain into Lewisboro. Thus, Oscaleta and Old Oscaleta Roads, now separated by a quarter of a mile of West Mountain Road, used to be one highway, which explains the connection between the two names.
For the origin of the name "Oscaleta," see Oscaleta Road

Old Pierce Road is a little lane, dirt until recently, off Danbury Road, named for Charles Pierce, who lived there. Mr. Pierce worked on the estate of Colonel Louis D. Conley, who in the 1920s owned most of the land on both sides of Danbury Road for his nurseries. The road was little more than a driveway.
In 1979, the road was improved to serve a subdivision of the property of Actor Cyril Ritchard, famed for his portrayal of Captain Hook in Peter Pan. Mr. Ritchard had lived in a house on the nearby pond until his death in 1977.

Old Quarry Road extends from Grove Street to the town transfer and recycling center, and the highway department depot. Somewhere near them, it becomes South Street (q.v.).
The road was so called from early in the 20th Century for an old stone quarry, which is still visible on the adjacent Schlumberger-Doll property on the south side of the road. The small quarry was worked in the 19th Century, perhaps even the 18th Century, probably to supply stone for foundations, basements, and fireplaces of Ridgefield homes.
The road was also called Dump Road as late as 1958 (when the name appears in the minutes of a Board of Selectmen's meeting). The dump started back around 1916 or 1917 when a few townspeople began tossing their trash on a small piece of land owned by William Peatt Sr. Mr. Peatt, according to the late Francis D. Martin, didn't mind. Soon, the area became the place to toss your garbage.
Mr. Peatt owned a little less than an acre and by the 1920s, it couldn't hold the wastes being disposed of there. Mr. Martin tried for three years to get the town to buy his own 10 adjoining acres. Finally, the town agreed, and paid $500 for what was to become one of the most important pieces of land in town. In the late 1960s, the dump became a landfill (a dump covered each day with fill). The landfill was closed in the early 1980s and replaced with the current transfer station system. The recycling center was established in the early 1970s.
Before a formal dump was established here, people disposed of their trash on the back corners of their property or at a mutually agreed upon neighborhood dump. These have become sweet pickings for bottle collectors. One of the best old dumps was situated on South Olmstead Lane, but is now covered with houses. Many dumps, buried with fill and by time, remain undiscovered and probably hold plenty of treasures for bottle and memorabilia collectors.

In 1777, the proprietors granted Benjamin Northrup one rood "lying in the Old Ram pen so called." The pen, along upper West Lane, was connected with the Ram Pasture (q.v.).

Old Redding Road is the proper term for the road that leads from Route 7 near Florida Hill Road into Redding. It is sometimes incorrectly called Seventy Acres Road (q.v.).
The name is derived from the fact that it was once considered a main highway from Ridgefield to Redding - or the Redding Road.
Probably the earliest mention of this route was a 1746 deed from Joseph Karley to Ephraim Jackson for "one piece [of land] lying on ye north side of ye road leading to Reading." The parcel was just across the present-day Route 7 from Miller's Pond.
Although today it is a road of its own, Old Redding Road in the 18th Century was merely a part of what we today call Florida Hill Road. Route 7 then was little more than a path, if that, and Florida Hill Road veered north just east of the Norwalk River on the route that made Old Redding Road its continuation.
Some maps, including the 1946 town zoning map and the official town map of 1960, labeled this road Seventy Acres Road. Why this was so is unclear. The road in Ridgefield is only about 500 feet long and then becomes Old Redding Road in Redding. It does not even connect with Redding's Seventy Acres Road, which is about a half mile away from the Ridgefield line, and off Mountain Road.
In 1964, when the town had a sign erected saying that this was Seventy Acres Road, Redding First Selectman Bart Sanford wrote Ridgefield First Selectman Leo F. Carroll, asking that the sign be changed to Old Redding Road. He cited confusion caused by the Ridgefield name - which did not match the Redding end of the road and had no connection with the real Seventy Acres Road. Mr. Carroll immediately ordered a new sign.
The name, "Redding," is derived from Colonel John Read, an attorney and land speculator, who in 1714 bought a large tract of land from Chicken Warrups, a local American Indian. Read drew up a formal patent, with Chicken Warrups as lord of the manor and himself as a tenant. The territory was called Reading by 1717 and by 1729, it was a parish of Fairfield. It broke from Fairfield and incorporated as a town in 1767.
Tradition, says Hughes' and Allen's Connecticut Place Names, maintains that the unpopularity of Colonel Read by the 1760s was so strong that people decided that the name "be not Reading, but Redding." However, it is more likely that the new spelling was adopted, suddenly or gradually, because it better reflected the pronunciation of the word.

Old Ridgebury Road is a name applied to the highway that veers off to the right - northeastward - from upper Ridgebury Road and runs into Danbury where it also bears that name.
According to the Daniel M. McKeon, who had lived more than 60 years in Ridgebury and was a student of its history, the name is incorrect. It should be simply "Ridgebury Road."
And he's probably right. There is no reason to call the highway "old" Ridgebury Road because there is no "new" Ridgebury Road that has replaced it. The highway is merely part of Ridgebury Road (q.v.) into Danbury's Mill Plain District (q.v.). Before 1846, when northern Ridgebury was ceded to Danbury, the entire length of the highway was within Ridgefield.
The highway called Ridgebury Road that veers off to the left - northwesterly - at this intersection should be considered Turner Road (q.v.), Mr. McKeon said. Town officials have considered Turner Road to be only the little lane that heads westward into New York State from Ridgebury Road at the Danbury line.
Old Ridgebury Road dates from the 18th Century and connected rural Ridgebury's center with the bustling little 19th Century business and industrial center of Mill Plain.

In 1856, Elias Gilbert quit claim a lease to Jabez Mix Gilbert for land in west-central Ridgefield, but mentioned that he was not giving up his right to draw water - presumably for a mill - from Upper Pond or from "the Old Saw Mill Pond." This reference is probably to Saw Mill Pond (q.v.) on the south side of Saw Mill Hill Road.
The adjective "old" probably referred to the fact that it was an early pond - or the earliest - of several mill ponds in this neighborhood, used to power the sundry mills at Titicus.

Old Sib Road, sometimes called simply Sib Road, is one of the biggest mysteries among Ridgefield's more than one thousand place names. Who or what "Sib" was has not been ascertained, despite considerable research.
Only one possibility, albeit remote, has so far been found.
Neither the name nor the highway is very old. The road does not show up on maps until the 20th Century, although it may have been an old logging trail in the 19th and maybe even 18th Century. The name, or a name like it, does not show up in any deed before 1885.
Sib itself is an unusual word that long ago fell out of popular use. One meaning, employed into the 19th Century, was "kinship" or "relationship." Another was "peace," based on an Old English root. However, that use was last known in the 13th Century!
Interviews with old-timers found no answer. The late Frank Baxter, whose family had lived in the neighborhood for more than a century, does not know the origin. As a child he called it "Port Road" (q.v.) because it led to the Port of Missing Men Resort atop West Mountain. (The restaurant was also called Anderson's Tea House, and the road "Anderson Tea House Road" (q.v.) or just "Tea House Road (q.v.)
The late Julius Tulipani, a former selectman who in his youth helped build the roads around the Port of Missing Men early in the century, knew the road only as Tea House Road. The late Francis D. Martin, who lived in Ridgefield some 80 years and along Old Sib Road for nearly 40 of them, did not know the origin.
The late John Mullen, another oldtimer, said in a 1975 interview that the name may have been a corruption of "Sid," nickname of Sidney D. Farrar. Mr. Farrar, a professional baseball player in the 1880s and father of opera star Geraldine Farrar, had a 30-acre farm on North Salem Road from 1923 until his death in 1935 (see Farrar Lane). While his land did not border Old Sib Road, it came close to the beginning of the highway at Tackora Trail.
Adding some weight to Mr. Mullen's suggestion are two 1951 maps for portions of the subdivision called Eight Lakes (q.v.), through part of which Old Sib Road runs. The two maps (town clerk numbers 2000 and 2001) label the highway "Old Sid Road." Map 2005 of the same series says "Old Sib Road."
Mr. Martin believed that the connection with Mr. Farrar was impossible because he recollected the road's being called "Sib" before Mr. Farrar had his farm nearby. The name made its debut on a map in 1946, when the town's first zoning map was published.
Old Sib Road was built around 1908 by laborers, including Mr. Tulipani, who were hired by H. B. Anderson. It was part of a network of roads designed for the recreation of users of his resort.
Many of the workers came here after having build a huge dam at Valhalla, N.Y., and quite a few settled here.
While narrow and unspectacular in appearance, Old Sib Road is among the best-built roads in town. According to James Loughlin, who moved to the road in 1952 and had done a little research into it, Old Sib Road is a Telford road, a design, named for its inventor, that employs a stone foundation.
Preliminary work on the road was done by a crew which took large, long stones and stood them on edge on the roadway. Next, a crew with small rocks came along and filled in the gaps between the large stones. Finally, another crew laid gravel and dirt atop the stone base. It was almost as if someone built a tall stone wall on its side.
"That road should be there forever," said Mr. Loughlin. "God help the contractor that has to come in and put pipe in under that road."
There have been places along the road where modern pavement has worn thin and the stone base can be seen. In some spots, the stones have projected through the pavement.
Old Sib Road, which begins at Tackora Trail, continues into New York State, where it becomes a dirt road in a Westchester County park located in the town of North Salem. The state line is marked with a granite monument on the north side of the road.
Some years ago, North Salem got tired of commuters using this road as a shortcut, and partiers parking along it and tossing their litter there. North Salem erected an earthen pile at the state line to prevent cars from entering the road.
Old Sib Road, one of the highest roads in town, reaches an elevation of 800 feet above sea level along its western end. In the days when it was lined with fields, it was famous for its vistas, particularly its view of Lake Mamanasco some 200 feet below. However, the return and growth of trees has blocked many views.

The lower half of town - that is, all below Ridgebury - was occasionally called the "Old Society" to differentiate it from the "New" or "Second" Society, which was Ridgebury.
For example, in 1772, Matthew Smith sold Lemuel Morehouse eight acres described as lying "near ye west corner of ye Old Society" (probably somewhere near today's Ridgefield High School).
In 1796, Josiah Hall sold Abner Gilbert land in "Ridgefield Old Society."
Mostly Congregationalists, who called their church a "society," settled Ridgefield. The term came to refer not only to the church group, but to the territory - or parish - that it covered. And considering the closeness of church and state in those days, the naming of a part of town as a "society" is not unusual.
Town and church government were nearly one in the early 18th Century. The townspeople had to apply to the State Legislature in 1712 to have a full-time minister. That first minister, the Rev. Thomas Hauley, received community land as compensation for coming here. He served not only the religious, but the temporal needs of the community, working as town clerk and probably as school teacher. And townspeople were taxed to pay his salary.
The Town Meeting voted in 1723 to build a "Meeting-house." This was no single-purpose building; for years it served as a church, town hall, and public schoolhouse. Thus, calling a part of town "Old Society" or "First Society" was not strange to theocratic Ridgefield.
The term would have had to come into use sometime after 1761 when the Second Society at Ridgebury was established - with permission of the State Legislature.

Old South Salem Road was the original route of South Salem Road (q.v.) as it entered New York state. The wider and straighter state highway bypassed the road in the late 1930s.
It is an old road, dating probably from the 1720s. The name will be discussed in more detail under South Salem Road.

Old Stagecoach is a name that accurately reflects this road's history.
The name applies today to an old highway from Ridgebury Road southward to Aspen Ledges Drive. The portion between Ridgebury Road and Bennett's Farm Road at the Ridgebury Firehouse was for years considered part of Bennett's Farm Road, but as a result of a 1961 petition by townspeople, the Board of Selectmen renamed it Old Stagecoach Road.
The section south of Bennett's Farm Road had been known as Old Stagecoach (or Stage Coach) Road since at least 1946, but was not a developed road until the late 1950s when Robert Kaufman built the Ridgefield Knolls. However, the whole route, plus a section now abandoned, were part of a highway dating back to at least the middle 1700s.
For many years Old Stagecoach Road was little more than a path through the woods. The rebirth of the roadway was recorded in the Feb. 9, 1950 Press, which reported:
"A few weeks ago, a John Morganti Company bulldozer blazed a fresh path over one of early Ridgefield's historical roadbeds up in Ridgebury. 
"Long overgrown with young saplings and weeds, the roadbed is still referred to by a few old-timers as the Old Stage Coach Road, a relic of the days when it was a stage route from Ridgebury to Norwalk...
"Climbing steeply in a southeasterly direction from Bennett's Farm Road near Pork Hollow Farm, the old road is still discernible between two parallel stone walls. Beyond the point where the Morganti bulldozer stopped (after penetrating slightly less than a mile into the woods), it winds further over the rough, wooden Ridgebury hilltop, picks its way down an almost perpendicular cliff known as 'The Ledges' and is lost somewhere in the Titicus River flatlands where it once connected with North Street...
"The area was once populated, though rather sparsely. The bulldozer trail winds past two or three old fieldstone foundations and chimney remains, at least one of which was built without the aid of mortar. Purpose of the recent activity in that section of Ridgebury is to redevelop it for residences.
"The Old Stage Coach Road nearly bisects a 220-acre tract recently purchased by Lawrence M. Samuel of Limestone Road from the estate of the late George R. Read. Mr. Samuel purchased the property ... for development and resale...
"The property at one time was part of the Rundle Farm, was purchased by George Read near the turn of the century..."
As shown on the town's 1946 zoning map, Old Stagecoach Road continued southwesterly from the modern-day intersection with Aspen Ledges Drive down a steep incline to Ledges Road, coming out a little east (and opposite) of Sherwood Road. This took it down some steep territory - called the Aspen Ledges - a drop of more than 300 feet in elevation over a distance of less than 2,000 feet. It must have been a precarious and uncomfortable trek for a stagecoach.
Beers 1867 atlas shows the route down the Aspen Ledges as going almost directly to the south. This steeper, more direct route may have been the one used by the stage. However, it may also have been a mapmaker's error. (The road does not appear at all on Clark's 1856 map, although it surely existed by then.)
The road's namesake was a stage line established in 1836 by David Hunt of Ridgebury, who lived in a house now owned by Daniel M. McKeon on Old Stagecoach Road, just below Ridgebury Road. Here, the stage left at 2:30 in the morning, bound for Norwalk to meet the steamboat for New York City. It waited in Norwalk for the next boat from New York.
Passengers traveling this line came from Danbury, Mill Plain, and other areas to the north. They could get rides to the Hunt house, where they awaited the stage's early morning departure.
This, of course, was in the days before the railroad. When the New York and New Haven's coastal line was opened in 1847 and the Danbury to Norwalk line followed in 1850, Hunt's run to Norwalk was made old-fashioned and tedious. Stages still ran to places like Branchville (Ridgefield Station) to meet the trains and bring passengers to and from the village, and perhaps runs up to Ridgebury existed, too. But even the village trips were obviated by the opening in 1870 of a branch railroad into the village, probably ending the era of the stage in Ridgefield. (Ridgefield had been on intertown and interstate stage routes probably since the first half of the 18th Century. A main line followed almost the whole length of Route 35 in Ridgefield for a stage that ran from New York to Danbury, and then probably on to Hartford.)
In 1994, the section of the old road was the subject of a dispute between a developer, who wanted to put some houses on the Ledges, and the Conservation Commission, which wanted the route of the old stagecoach road preserved. The developer did not want to rearrange the lots and felt the true route of the old roadway is unclear and unknown.
Old Stagecoach Road is not an uncommon name. There are at least a dozen others in Fairfield County.

Old Still Road was apparently another name for Still Road (q.v.). It appears on a 1915 property map filed with the town clerk's office. It probably referred to the old still once operated here rather than to the age of the road.

Old Stone Court is a 600-foot, tertiary road off Bobby's Court, created by Lewis J. Finch's 1985 subdivision of 10 acres into five lots.
The name, approved by the Board of Selectmen in 1987, is one of those meaningless road names that appear in countless subdivisions. In this case, the name sort of states the obvious - all stone is "old." Stone has been made around here in millions of years. And certainly the road, created in the mid-1980s, hardly qualifies as being old.

Old Town Road is a short lane between Route 7 and Wilridge Road, developed in the 1950s by Joseph L. Dioguardi (1910-1989). Sometimes appearing as Olde Town Road, the name was selected by Mr. Dioguardi to reflect research he did into the road, one of several he developed in the neighborhood.
According to a letter written by him to the Board of Selectmen in 1963, Mr. Dioguardi searched the title of the road back to 1759 and found that it originally extended through Wilton to Pelham Lane at Nod Hill Road. Since its connection with Route 7 is very close to the Wilton line, it is possible that the road was created by Norwalk settlers to run along the northern border of Norwalk - an easterly continuation of Pelham Lane. (Wilton was part of Norwalk in the 17th and 18th Centuries.)
The developed section was accepted as a town road in 1964.

Old Trolley Road, long a short, dead-end road off the east side of Ridgebury Road between George Washington Highway and Shadow Lake Road, was much expanded in the 1990s in the Stone Ridge subdivision.
The road originally served several lots that were the only part of Otto H. Lippolt's 1959 "Ridgebury Acres" subdivision of 72 lots that were ever developed.  The road was extended in the Stone Ridge subdivision, and many more houses built along it.
The name preserves a little-known and unsuccessful episode in Ridgefield's history. In 1894, an "electric street railway" was started up in Danbury, and formally began operations Jan. 1, 1895. Various routes were established, including ones to Bethel, to Lake Kenosha in Mill Plain, and to the Fair Grounds (now the mall) and on to Ridgebury. (I have seen an account of the first trolley trip to Ridgebury, but for the life of me, I cannot find it.)
The trolley tracks in Ridgebury may have been laid on a bed that had been created years earlier. In 1850, the New York, Housatonic and Northern Railroad was established on paper, and issued $1 million in stock to build a 40-mile-long railroad from White Plains to Brookfield, passing through Ridgebury and Danbury.
A rail bed was actually constructed for much or all of the route. It entered Ridgefield from North Salem just north of Chestnut Hill Road, traveled through swamp and the present Dlhy Ridge Municipal Golf Course, and came out onto Ridgebury Road at Benson Road. There, it traveled up the middle of Ridgebury Road for about a third of a mile, veering off to the east over what's now Old Trolley Road, then heading southward, crossing George Washington Highway and running east into Danbury.
In North Salem, N.Y., much of the old railbed is visible as it wanders through back country and eventually can be seen along Route 121 as the road heads south to Cross River.
While the bed was built and is still clearly visible in many places, the complete tracks were apparently never laid. Financial problems in the company apparently spelled doom for the enterprise.
However, a short section of track was laid by 1869 between Danbury and Brookfield, and these were later taken over by other railroads. These tracks are still in use today.

Old Wagon Road, a 1,600-foot dead-end road off West Mountain Road, is part of the Eleven Levels subdivision (q.v.), a development for which Jerry Tuccio received approval in 1969. The road was accepted as a town road in 1978.
The name probably suggests that the road - or part of it - was an old farm path.

Old Washington Road is indeed old. It may not, however, commemorate our first President.
The road, which originally ran between Branchville and Florida Hill Roads, now has a dead end before it reaches Florida Hill Road.
Bert Ison improved the southern part of the road and developed the land along it. His subdivision, which includes other newer roads, is called Washington Park Estates after the road.
Mr. Ison said in an interview years ago that the late Raymond and Robert Keeler, whose family had lived since the 18th Century in this neighborhood, told him that the road was not named for George Washington. Instead, it recalls Ridgefield's "hermit," George Washington Gilbert (1847-1924), who once lived near where Old Washington Road crosses the old railroad bed. Mr. Gilbert, a town character in the late 19th and early 20th Centuries, was covered under Hermit Lane (q.v.), another road named for him and located near the old northern terminus with Florida Hill Road.
Old Washington Road was called Washington Street on the 1946 zoning map.

Old West Lane was a 20th Century term for a Ridgebury road, part of which is now called Canterbury Lane (q.v.).
As early as 1799, deeds mention "West Lane," a highway that ran westerly from Ridgebury Road opposite George Washington Highway, to the New York State line. We have been unable to ascertain whether it met with another road in that state. Beers 1867 atlas shows it as an unimproved road while maps from 1856 and 1908 do not even acknowledge its existence. It was probably laid out in the 18th Century as a route to North Salem - a westerly extension of George Washington Highway (q.v.) - but fell into disuse, perhaps because there was no suitable continuation of it in New York.
By 1879, a deed was labeling the road "an old highway called West Lane," a description that was eventually converted into Old West Lane.
On Aug. 24, 1969, the Planning and Zoning Commission approved changing the name to Canterbury Lane because land along it was being subdivided for houses and the commission feared there would be confusion with the West Lane that runs from Ridgefield village into Lewisboro.

Although there is an Old West Mountain Road and a West Mountain Road, the "old" road does not follow the usual naming rule.
Both Old West Mountain and West Mountain Roads (q.v.) are old, dating from the 18th Century and serving different purposes. Unlike many other "old" roads, Old West Mountain Road was not an older road for which a newer one was built as a substitute. The name simply refers to its being an old road on West Mountain.
Old West Mountain Road connects Barrack Hill Road at Four Corners (q.v.) with West Mountain Road. Its purpose was probably as a route from the northern or north central part of town to South Salem village. It was also an access to fields and woodlots on the mountain.
Silvio Bedini suggests that Old West Mountain Road may have been part of an Indian trail that connected the Indian settlements at Lake Mamanasco with other settlements in New York state, particularly at Mud Pond in Pound Ridge. The fact that the Indians had a fort somewhere on Barrack Hill (see Fort Hill), near the north end of Old West Mountain Road, adds plausibility to the Indian-trail theory.
Old West Mountain Road is a 20th Century name. In the 19th Century, it was sometimes called Burt Road (q.v.) because members of that family owned much of the land along it. Even a 1940 deed, using an old property description, calls it Burt Road.

Old West Road was another name for what is today called Pumping Station Road (q.v.). The term was used as late as the 1930s and early 1940s, but it is not known when the name first came into use. The name is derived from the fact that the road heads west into New York State.

Olmstead Lane, a short road that runs between West Lane and Wilton Road West, is an old highway that bears the name of an old Ridgefield family.
The road probably existed by the 1750s, perhaps serving more as an access to fields than as a highway. It is said that some of the British soldiers moved along this road in April 1777 after the Battle of Ridgefield and while on their way to their overnight camp on Wilton Road West.
That it should be called Olmstead Lane is fitting. Five houses along this short road were either built or owned by members of the Olmstead family (four of those houses still stand). All five were along the leg between West Lane and South Olmstead Lane.
Probably the first of the Olmstead houses was the Stephen Olmsted place, at #75 Olmstead Lane. This dates from sometime in the middle 1750s. Other Olmstead houses are at 91 and 90 Olmstead Lane, and at the corner of Olmstead and West Lanes. The fifth house, just north of the Rosa place, was razed in the 1950s, though a new house was being built on the site in late 2005.

Old Family
The Olmstead family is an ancient one in this country. Brothers Richard and James Olmstedd and James' nephew, John, came from England in 1632 to Boston. Richard, who eventually moved to Hartford, became one of the petitioners for the founding of Norwalk and, as a settler there starting in 1650, held various important militia and government positions.
Richard's sons, Richard and Daniel, were among the first settlers of Ridgefield.
From this family over the next two centuries sprang a couple of hundred Ridgefield Olmsteads. At least a dozen of them served in the Revolution. Four were officers and two were fairly notable soldiers. One of them was Capt. David Olmsted, about whom the Red Petticoat legend is told (when he learned his wife waved a red petticoat at passing British troops to save their house from being burned - red being a loyalist color - he reportedly yelled: "Woman, if I had seen you, I would have shot you dead.") The other was Matthew Olmstead, a guard over Major John Andre at the time of the famous spy's execution.

The Wit of Mat Olmstead
Whether this is the same Matthew Olmsted of whom S.G. Goodrich wrote in his 1856 Recollections of A Lifetime, is not certain. Goodrich called him "Mat Olmstead, the Village Wit" and said of him:
"He ... was a day laborer, and though his specialty was the laying of stone fences, he was equally adroit at hoeing corn, mowing, and farm-work in general. He was rather short and thick-set, with a ruddy complexion, and a mouth shutting like a pair of nippers - the lips having an oblique dip to the left, giving a keen and mischievous expression to his face, qualified, however, by more of mirth than malice. This feature was indicative of his mind and character, for he was sharp in speech and affected a crisp, biting brevity, called dry wit. He had also a turn for practical jokes, and a great many of these were told of him, to which perhaps he had no historical claim."
To illustrate this, Mr. Goodrich told the following story, which happened, it was said, one December night in the early 1800s in the bar-room of the Keeler Tavern, where Mat and his friends were "lounging."
A stranger happened in, wearing a "new hat of the latest fashion, and still shining with the gloss of the iron. He seemed conscious of his dignity, and carried his head in such a manner as to invite attention to it. Mat's knowing eye immediately detected the weakness of the stranger."
Goodrich relates the encounter as follows:
"What a very nice hat you've got on," (said Mat). "Pray, who made it?"
"Oh, it came from New York," was the reply.
The stranger took off his hat, gingerly, and handed it to him.
"It is a wonderful nice hat," said Matthew, "and I see it's a real salamander."
"Salamander?" said the other. "What's that?"
"Why a real salamander hat won't burn!"
"No? I never heard of that before. I don't believe it is one of that kind."
"Sartain sure; I'll bet you a mug of flip of it."
"Well, I'll stand you."
"Done. Now I'll just put it under the fore-stick (in the fireplace)?"
It being thus arranged, Mat put the hat under the fore-stick into a flowing mass of coals. In an instant, it took fire, collapsed, and rolled into a black, crumpled mass of cinders.
"I du declare," said Mat Olmstead, affecting great astonishment. "It ain't a salamander hat arter all. Well, I'll pay the flip!"
Mat, about whom Goodrich tells other stories, lived in "a little brown tenement situated on a lonesome lane that diverged to the left from the high-road to Salem." The lonesome lane was Olmstead Lane and the "tenement" may be what is in 2005 the Harrington home at 90 Olmstead Lane.
The road has a long history of residents prominent in civic service, dating back to those who served in the Revolution through the 19th Century to modern times. Perhaps the most notable 19th Century son was James Harvey Olmstead, born at 75 Olmstead Lane in 1830, who went on to become a district attorney, judge, and state central committeeman (Democratic) in Stamford. In recent years, Olmstead Lane has been the home of a postmaster, a Board of Finance chairman, the chairman of the Historic District Commission, a school board chairman, a former probate judge, and town attorney. It has also been home to authors, artists and actors.
Olmstead Lane was so called at least by the turn of the century when the name appears on a state highway department right-of-way map for Wilton Road West. The name does not appear on the land records before 1885.

Ed or ead?
The family name in Ridgefield was originally spelled Olmsted. Early in the 19th Century, the conversion to Olmstead began. The first "ead" spelling in the land records appeared in 1829.
An interesting document found in the attic of one of the Olmstead houses graphically shows the transition in spelling. Consisting of several pages from the school notebook of David Olmstead (1835-1855), the 1850 document has examples of the 12-year-old boy's writing exercises. On one page, David practices his own name 14 times. The first through sixth examples say "David Olmsted" while the seventh comes out "David Olmstead" and then the rest return to Olmsted.
It appears that David's teacher had written down examples of handwriting to copy for penmanship practice. David spelled his name Olmstead, though not everyone in the clan did, and the teacher apparently used the traditional spelling. Not one to go against his teacher's directions, David spelled his own name incorrectly 13 times, slipping only once into the correct spelling he was accustomed to.
Within the large clan throughout the country, there are still many people - perhaps 50% of them - who spell the name Olmsted.
In Ridgefield a few people with Olmstead blood remain, though no one is left who bears the name. 

O'Neill Court is a road off North Salem Road, part of the 1982 subdivision by Joseph H. Donnelly called "Scotts Ridge."
The name recalls playwright Eugene O'Neill, who lived from 1924 to 1927 in a house across North Salem Road from the subdivision.
While Ridgefield has been home to many writers, clearly Eugene Gladstone O'Neill (1888-1953) was the most noted and has been called "America's preeminent playwright." He won four Pulitzer Prizes - for Beyond the Horizon (1920), Anna Christie (1921), Strange Interlude (1928), and Long Day's Journey into Night (1956) as well as the Nobel Prize for literature in 1936).
Born in New York City in 1888, O'Neill was the son of James O'Neill, a poor Irish immigrant who became a leading stage actor of his time. In 1906, he went to Princeton University but was soon suspended for a prank and never returned. In his early years, he was a seaman in New York and a reporter in New London. While recovering from tuberculosis, he was taken reading by Stringberg plays and in 1914 enrolled in a playwrighting program at Harvard.
His first marriage in 1909 ended in divorce, and in 1918 he married Agnes Boulton, a fiction writer. Their daughter, Oona, born when the O'Neills lived here in 1924, became the wife of Charlie Chaplin, the noted film comic. The second marriage ended in divorce in 1929. He died in Boston in 1953.
While a Ridgefield, Mr. O'Neill led a quiet life with Agnes, Oona and his young son, Shane. (See also Notable Ridgefielders on this website.)

Orange Ridge was a bastardization of Norran's Ridge, which in turn was a corruption of Nawranawoo's or Norranorwa's Ridge. It referred to the ridge behind Fox Hill Village condominiums on Danbury Road and north of Farmingville Road at Great Swamp. The recently develop Norrans Ridge Road traverses part of this ridge and took its name from these older names.
Orange Ridge was used by George L. Rockwell in his History of Ridgefield.

Orchard Lane is a private, dead-end, dirt road off St. John's Road, part of a 1956 subdivision by Warren and Elizabeth Simmons. The name probably reflects a former use of the land in the area of the road.

Orchard Street was the original name for the road that we today call East Ridge Road.
The name first appeared in an 1880 deed in which Lewis H. Bailey sold Hiram Davis an acre bounded on the north by "Prospect Avenue" and on the west by a highway "known as Orchard Street."
The name also appears in 1912 on Whitlock's Atlas. At around the same time, the road was also being called Middle Ridge. Oddly enough, neither name won out, and "East Ridge" came into and remains in common use.
An orchard, possibly owned by the Lounsbury family (see Governor Street), was undoubtedly the source of the road's name.

In 1830, Sarah Warren sold Reed Haviland land "near and west of the house of said Haviland and known by the name of the Mine Lot or Ore Bed."
The Ore Bed was a limestone mining operation near or at the intersection of Haviland, Danbury and Limestone Roads. It was discussed in some detail under "Mine Lot."

In about 1717, the proprietors gave Henry Witne (Whitney) eight and a half acres "lying in a place called ye Ore Yard." 
There is no clue in the deed as to its location or purpose, but the Ore Yard may have been the Ore Bed mentioned above.

Oreneca Road is an old highway on West Mountain. The name today applies to the road as it runs between West Mountain Road northwesterly past Rippowam Road and up to Girl Scout Camp Catoonah and a Norwalk YMCA camp, where it becomes private property.
Legend says that this road was part of an Indian trail that ran from Lake Mamanasco over Old West Mountain Road (q.v.), Rippowam Road and into New York State to Mud Pond in Pound Ridge. It was probably this story that led Ridgefielders in the late 19th or early 20th Century to select Indian names for this and Rippowam Road (q.v.). 
Or perhaps the roads were named after the nearby lakes of the same name in Lewisboro, N.Y.
Oreneca was a sachem of the Ramapoo tribe, the Indians who inhabited Ridgefield when the settlers arrived. The name also appears as Narranoke, Naraneka, or Noroneke. According to the minutes of a proprietors' meeting in 1715, he was "Tackora, alias Oreneca."
Little is known about this Indian, who probably left with his people for parts west after the Indians' interest in Ridgefield lands was sold. In the first Indian deed to the settlers (1708), he was one of eight signers, and was listed as "Naraneka." In the second deed (1715), he signed alone as "Oreneca, alias Tackora." In the third deed (1721), the last he signed, he was "Norreneke." (It's little wonder that Oreneca Road is spelled incorrectly so often by the average Ridgefielder today!)
Catoonah, the head sachem of the local Indians, had land in what is now Pound Ridge, where he died. Perhaps Oreneca moved there, or farther west.
The name Oreneca is not all that unusual, and may have been a common Indian word. Similar sounding names appear in Connecticut geography: Oronoka in Stratford, Oronoke in Waterbury, and Oronoque in Milford and Stratford. Various Fairfield County localities bear or bore names like Oronauke, Oronooke, Orronack, and the possibly related Noronoco. John C. Huden translates the basic set of sounds as "curved place" or "land at the bend," and says it was a Quinnipiac word. Probably purely coincidentally, the meaning is perfect for the road, which was once part of that Indian trail with a couple of notable bends (at West Mountain and at Rippowam Roads).
Even in the language of Indians of the Virginia region, there was a word, oronacah, meaning any ground that had been planted with corn.
In the 18th Century, Oreneca Road may have been part of the original West Mountain Road, and travelers would have had to go northerly up Oreneca to Rippowam, and then south to Old Oscaleta Road, which led into the South Salem part of Lewisboro. The shortcut from near Old West Mountain Road to the lower end of Rippowam Road may have been established sometime between 1856 (when it does not appear on Clark's map) and 1867 (when it does appear on Beers' map).
Why Oreneca and Rippowam Roads managed to stay in use after the shortcut was built is unclear; most roads leading to "nowhere" in the "outback" were abandoned when bypasses were established. It is possible that Oreneca Road served as a handy route to woodlots along the western border of town as well as as a path to the southern and western shores of Round Pond.
It is not known whether Oreneca and Rippowam Roads preceded the flatter Oscaleta Road as the route to northern Lewisboro.
When David L. Paul was developing his apartment-condominium project on Danbury Road around 1970, he considered calling the place Oreneca Village because there was an old Indian burial ground on nearby Norran's Ridge. The few residents of Oreneca Road, particularly the late Harrison Horblit, immediately objected on the grounds that their mail would end up on Danbury Road or the apartments' mail would end up on Oreneca Road.
Mr. Paul gave up and instead selected Fox Hill Village - recalling the fact that Col. Louis D. Conley of Fox Hill in Bennett's Farm district had once owned the Outpost Inn on Mr. Paul's property.
Oreneca Road was so called by 1907 when the name appears on a property survey, on file in the town clerk's office. Years ago, it was sometimes called Oreneca Trail.

A postcard from around 1920 shows a view which is labeled: "Lake Oreneca (Round Pond) and Dr. John G. Perry's Residence." The name was probably used by Dr. Perry or perhaps H. B. Anderson, whose house was nearby, because it was more colorful than Round Pond. Obviously, the name didn't stick with the pond.

Oscaleta is an unusual word that has tricked many into believing it is of American Indian origin. It is, in fact, a word from a dialect of Spanish and means "little kiss." Its roots are in the Latin word, osculum, "to kiss," and the archaic Spanish, osculo, plus a diminutive suffix. The English word, osculate, is a fancy way of saying "to kiss."
In nearby Lewisboro, N.Y., a body of water was named South Pond or South Lake in the 19th Century. According to Stanley Newton, a student of Lewisboro history, a man named Richard Hoe Lawrence, a wealthy fellow who had spent much time in Spain, returned to the United States and a gentleman's farm and lodge on South Pond in the late 1800s. He apparently felt South Pond was too bland a name and, perhaps inspired by the shape of the pond, used a word he had heard and liked in Spain, naming it Lake Oscaleta.
The nearby old road in Lewisboro picked up the name as well, presumably because it was the road that led to Lake Oscaleta. That road runs into Ridgefield's West Mountain Road. Long ago, the western section of West Mountain Road followed the same path as today's Oscaleta Road; it was considered the Connecticut extension of Oscaleta Road.
At the state line, there is still a section of the original old highway, today called Old Oscaleta Road. It is separated for a short distance from Oscaleta Road by the highway we now call West Mountain Road, which was originally a piece of Oscaleta Road.
It is possible that Oscaleta Road was the original main road to upper South Salem (Lewisboro), for it is flatter than the alternate route that, before 1850, would have taken people over Oreneca and Rippowam Roads. It is also possible that Oscaleta Road was built around 1800 as a bypass to the more hilly route. Both routes are very old.
Oscaleta Road in Ridgefield has been so called since at least 1907 when the name was used on a property survey on file in the town clerk's office. Some Westchester County histories spell it Oscaletta, such as in Oscaletta Lake in Westchester County and Its People (1946). However, Richard M. Lederer, in his The Place Names of Westchester County, N.Y. (1978), uses the Oscaleta spelling as does A History of the Town of Lewisboro (1981). The old T. H. Mead estate on lower Rippowam Road was called "Oscaleta" early in this century.

A deed written in 1835 mentions land "at Otter Pond." From landowners mentioned in the property descriptions, including Selleck, Whitlock, Dan, and Thrall, it appears that the pond was situated in the vicinity of the Ridgefield Lakes (q.v.), perhaps at or near Fox Hill Lake (itself, man-made).
The pond evidently no longer exists or has been supplanted by one of the more modern Ridgefield Lakes. 
Sometimes called "the playboy of the wild," the otter is a fairly common member of the weasel family, still found along some of our streams, where its frolicking can be observed by those patient enough to seek it out. Otters were undoubtedly more common in the agricultural Ridgefield of 1835 than in the subdivided suburb of the 1990s, but sightings are still not all that unusual.

Outpost Pond on Danbury Road is a small body of water whose name is connected with one of the biggest commercial operations Ridgefield has ever seen - the 1,500-plus acre Outpost Nurseries, and it is odd that something so big should be recalled by something so small.
The pond was built by Col. Louis D. Conley in the late 1920's, but probably didn't pick up its name until Colonel Conley established his Outpost Inn two months before his death in 1930. It was a famous dining spot, drawing people from miles around for nearly 30 years.
The Colonel, who once led the New York National Guard's "Fighting 69th" Division, built an estate like few others the town has ever seen. At the height of the operation, he owned almost one-tenth of the town, some 30 or 40 houses in which his staff lived, a huge mansion for his family, a sizable farm, kennels for championship dogs, and even his own electrical generating plants and water supplies.
Little of the man-made splendor remains as it was. His 34-room mansion became the Fox Hill Inn along eastern Bennett's Farm Road after 1946, but was torn down in the mid-1970's by the new owner, IBM. The kennels, where later the Coast Guard trained dogs and Gaines tested chow, are now the Red Lion Restaurant. And the inn, damaged by fire around 1970, was torn down. Before the fire, David L. Paul had planned to use the inn as a community building for his Fox Hill Village. He considered calling the apartment and condominium complex "Outpost Village," but the Conley family, which still used the business name, disliked the idea.
What mostly remains of the Outpost holdings represents Colonel Conley's greatest contribution to Ridgefield: thousands and thousands of trees.
Born in 1874, Louis D. Conley grew up in New York City where he spent most of his life and where he and his two brothers took over their father's Conley Tinfoil Company, a major U.S. industry of the era. Around 1914, tiring of hot summers in the city, Colonel Conley bought the old Selleck house atop the hill as an "outpost" from New York City.
"It was the most beautiful place in the state of Connecticut and the most difficult to run," said the late Julius Tulipani of High Ridge, who was superintendent of Outpost Farms starting in 1919.
The estate was almost a small, self-contained empire, growing its own crops, raising livestock, operating its own water system with a 90,000 gallon storage tank, and supplying its own generating plant (the generator had two, 4,500-pound flywheels); later, Colonel Conley became one of only a handful of people in the country who set up wind-powered generators.
Most of the people who worked on the farm lived there in houses supplied by the Colonel. They included families whose names are well known in town today: Marinelli, Cassavechia, Servadio, Baldaserini and of course, Tulipiani.
Even when he was wintering in New York City, Colonel Conley made use of his Ridgefield farm. He would have fresh milk and butter, packed in ice, sent to the city on the 7:32 a.m. train out of Ridgefield.
In 1923, at the suggestion of a friend, Colonel Conley - who had sold off the family business - established Outpost Nurseries, primarily as a hobby. It wound up a giant business venture. The colonel began buying many pieces of land and eventually owned virtually every parcel along Danbury Road from today's "Gasoline Alley" to Route 7, and almost all of the land along Route 7 from Farmingville into Danbury, plus most of the land between - some 2,000 acres.
He (and his successors) planted hundreds of thousands of trees and shrubs. Most, of course, were sold, but thousands still remain, nursery stock that has now turned into woodland.
Many names of modern roads serving subdivisions on former Outpost land carry the names of the kinds of trees that had been planted there years before. There's Copper Beech Lane, where the copper beeches grew and still grow; Poplar Road, Birch Lane, Linden Road, Cherry Lane, Dogwood Drive and Laurel Lane. In addition, there's Nursery Road.
Outpost Nurseries became one of the largest retail nursery businesses in the East. Among its many jobs between 1925 and World War II were plantings of the 1933 Chicago World's Fair; the 1939 New York City World's Fair; the National Art Gallery in Washington; parks along Riverside Drive and elsewhere in New York City; Harvard, Yale and Williams colleges; Narragansett and Monmouth Raceways; and the estates of such people as Cole Porter, Lowell Thomas, Gov. Thomas E. Dewey, President Franklin D. Roosevelt (at Hyde Park), Walter Winchell, Robert Montgomery, and the Buckleys at Sharon.
The business was doing so well that nurseries were set up in New Jersey, South Carolina, Pennsylvania, and Long Island to grow trees and shrubs that couldn't be raised in Ridgefield's climate or soil. An office was maintained on Park Avenue in New York while the main office was on Route 7, just north of Route 35, in the stone building that's the centerpiece of Stonehouse Commons (just north of the Red Lion).
In 1928, Colonel Conley bought the Danbury Road house, built in 1812, that was to become the Outpost Inn. It opened in July 1930, and over the years, was leased to various restaurateurs including the late Joseph J. Gibney and Laurence I. Graham (who became Wilton's first selectman in the early 1970's). The pond was probably built in 1928, the same year the state abandoned the road that runs into the Fox Hill Village property and replaced it with the straight strip of Route 35 now in use.
In the early 1960's the building served as part of the Shapley School for boys (later co-ed; see Shapley Stretch), which went bankrupt. Mr. Paul bought the property in a 1968 foreclosure auction, and chose the name Fox Hill for his development because Colonel Conley's mansion was situated on that hill.
For many years, Outpost Pond was probably the most popular skating pond in town. With the arrival of the condominiums, public skating ended.
Colonel Conley died Sept. 7, 1930. An editorial in the Danbury Times said: "The colonel has done much to beautify Ridgefield. Attractive buildings have been created, and hundreds of waste acres (that) had been allowed to run to scrub and wild growth, have been cultivated, graded and planted." The nursery became "a splendid public park, running for miles along both sides of roads between Danbury and Ridgefield."
After the colonel's death, the family operated Outpost Nurseries, continuing a large business employing 200 or more people. In 1945, the family sold to the late J. Mortimer Woodcock, who had been the manager (and was from 1967 to 1971, Ridgefield's first selectman). Mr. Woodcock bought only 10 acres, but leased 1,000, and changed the name to Woodcock Nurseries.

Overlook Drive is a road with a semicircular path, attached at each end to Ramapoo Road. Its "overlook" is to the east, its best views being from the westernmost curve of the road, where the elevation above sea level is nearly 720 feet.
The road was part of the 1956 subdivision, Ramapoo Hills (q.v.), by Judge Joseph H. Donnelly. The land was once the Conklin dairy farm.
Overlook Drive was accepted as a town road in 1963.

Overlook Groves is a 1985 subdivision of 27 lots on 66 acres east of Limekiln Road. The lots are served by Nursery Road and Whitewood Hollow Court (q.v.). The subdivision was created by the Crosswicks Company of Wilton.