Bicycle trips in SW Connecticut and upper Westchester

20 journeys of 5 to 50 Miles in southwestern Connecticut and northeastern Westchester County, New York

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We live in a beautiful part of the country, rich with varied terrain, verdant fields and forests, and handsome homes, both new and old. One of the best ways to get out and enjoy the villages and countryside is on a bicycle.

Here are 20 trips, all designed to take advantage of some of the better bicycling roads and the nicest scenery we have. Ours is hilly territory, but many roads skirt the rough hills and generally stick to flatter valleys. Many of these are included.

The trips vary from about five miles to more than 40. All are "loops" that return to a starting point, which happens to be in Ridgefield. However, the starting point is really relative and, of course, you could begin your journey at any place along the line. What's more, with a good map, you can find shortcuts or long-cuts of your own, variations or even combinations of these routes. If you are an average bicycler, we recommend that you go in the direction given for the loop; riding in the other direction may sometimes offer steep grades.

At the end are two "return routes." At the fountain at Routes 33 and 35, Ridgefield is 800 feet above sea level. No matter how you slice it, you must do a bit of climbing to reach the village, especially from the south. However, some routes are easier than others, and we've described these and cited them in the trip descriptions.

We recommend that you always carry a map that includes your route.  A compass is good to have, too, if you're unfamiliar with the territory and may lose your sense of direction -- especially easy on a cloudy day. We have begun carrying a small GPS (Garmin 60CSx), which has every paved and most dirt roads in North America.

Some of the trips include dirt roads -- usually well-maintained with clay tops. However, if you are riding after a recent, heavy rainfall, some of these roads may be muddy or at least soft, making them harder to negotiate, especially with thin tires.

One final note: because this area has a lot of traffic, I usually do long trips early Sunday mornings when few cars are on the road. It's also a beautiful time to bicycle, free of traffic noise and exhaust fumes.--Jack Sanders


Around Silver Spring

About: Five miles. Few hills, mostly flat. Trip includes scenic Silver Spring Swamp, Silver Spring Country Club, fields and woods.

Towns: Ridgefield.

Route: Park at First Congregational Church, corner Routes 33 and 35. From fountain, head west on 35 toward New York, but take first left onto Olmstead Lane, south bearing right at intersection onto South Olmstead Lane, to St. Johns Road, bear right. Follow St. Johns south about 1/3 mile, bearing right at intersection with Silver Hill. Take left on Silver Spring Lane and follow to end, then right on Silver Spring Road. Bear left at intersection with St. Johns (scenic pond will be at your right). About quarter mile north on right will be Silver Spring, noted local spring, marked only with open space signs. Farmers in the 1700s came here for the best water. Continue north past pretty farmhouses with fields where you can sometimes see coyotes and wild turkey, as well as bluebirds. Bear right at end of Silver Spring and merge onto Route 35, back to church.

State Line Loop

About: 10 miles. One steep hill, otherwise easy. The trip takes you through woods and some horse country.

Towns: Ridgefield, Lewisboro.

Route: From center, follow Route 35 from fountain toward New York State. At second left (before Little Red Schoolhouse), turn left, then immediately bear left again onto Silver Spring Road. Follow south about 3.5 miles into Wilton and then, when the road turns to dirt, Lewisboro, N.Y. Watch for first right, East Street, also dirt. Follow East Street across bridge at end of scenic Brown's Reservoir, which serves Norwalk. East Street climbs a steep but short hill. At top, right onto Lockwood Road and follow Lockwood to its end at Elmwood Road. Right on Elmwood about 1.5 miles to its end. Right on West Lane back into Ridgefield. Right on Route 35 back to fountain.

The Two Ponds

About: 10 miles. No steep hills, two pretty ponds and two interesting parks are among the features of this easy-to-handle trip.

Towns: Ridgefield.

Route: Take Route 35 (Main Street) north to stop sign at Route 116. Cross to 116, but then bear right at the cemetery fork onto North Street. After about 2.5 miles, right onto Barlow Mountain Road, past Pierrepont State Park _ great for hiking and fishing. Continue a short distance beyond pond to Ledges Road on left. Follow Ledges to stop sign at Ridgebury Road; left on Ridgebury to Route 116. Right on 116. In a few hundred feet, Richardson Park is on left, providing good picnicking and light hiking area; continue few hundred more feet to left on Mamanasco Road, skirting Mamanasco Lake, Ridgefield's largest body of water. Mamanasco ends at Tackora Trail, turn right, then left at the stop sign to Route 116 (North Salem Road). Right on 116 back to Route 35 in village.

Lower Ridgebury and Ledges

About: This 14-mile trip around the lower part of Ridgebury and "The Ledges" has only one fairly steep hill and is ideal for cyclers wishing to build their strength for longer journeys. Plan to stop and explore Pierrepont State Park.

Towns: Ridgefield

Route: From center of Ridgefield, take Route 35 (Danbury Road) past commercial district and condos to light at Limestone Road; veer left onto Limestone through portions of the Ridgefield Lakes section of town; after about 1.5 miles, road becomes Bennett's Farm Road; continue past Ridgebury Elementary School to stop sign at Old Stagecoach (Ridgebury Firehouse is at left); bear right up hill along Arigadeen Farm, last working farm in town; right onto Ridgebury Road and very soon, left onto Chestnut Hill Road; left onto Spring Valley Road and follow to its end at stop sign at lower Ridgebury Road; right on Ridgebury to stop sign; cross straight onto Ledges Road which runs "under" the Asproom Ledges, once mined for coal and other minerals; right at stop onto Barlow Mountain Road past Pierrepont Pond and entrance to Pierrepont State Park; left at stop onto North Street, which leads back into village; at end, where it meets Route 116 (North Salem Road), go straight; about a block beyond, at next stop, merge straight onto Route 35 (Main Street) and return to village.

Along the Line

About: 18 miles. A few medium hills; one short steep hill. This route takes you through woods and by many old houses and elegant estates.

Towns: Ridgefield, Wilton, New Canaan, Lewisboro.

Route: From center, follow Route 35 from fountain toward New York State. At second left (before Little Red Schoolhouse), turn left, then immediately bear left again onto Silver Spring Road. Follow south into Wilton; road turns to dirt in Lewisboro, N.Y.; pass East Street and bear right at intersection with Wilton Road; Silver Spring becomes Bald Hill Road; turn right onto North Wilton Road and, as you're going downhill, watch for Valley Road on left; follow Valley south about 3 miles to Route 106; straight on 106, then follow it when it turns right; at top of gradual incline, right onto Canoe Hill (very steep but short incline at beginning); bear right at Brushy Ridge; follow to Route 123 (Smith Ridge), turn right and follow into New York; just north of Vista, by brown church, take right onto Elmwood Road, follow north to end, right on West Lane to Route 35 and back to center.

The Two Salems

About: Approx. 20 miles. A few mild hills. A trip through scenic Titicus River Valley and the horse country of North and South Salem areas.

Towns: Ridgefield, North Salem, Lewisboro.

Route: From center of Ridgefield, take Route 116 north into New York. Left at Route 121 through pretty village of North Salem, past famous Balancing Rock (a glacial deposit). Continue south on 121, past many horse farms. After a few miles, you will pass Route 138 on right. About a mile later, still on 121, turn left on School Road, a dirt road past modern mansions. At end, right on Mead Street, to Route 35, left to return to Ridgefield. You can get off 35 for a while by taking left onto quieter Spring Street shortly after the South Salem Firehouse. This will bring you into South Salem village. Keep right on Spring Street and you will wind up back on Route 35 near Connecticut line.

Over Dingle Ridge

About: 20 miles. One big hill, a couple small ones. This takes you past some of the most scenic territory in the area and is well worth the little extra effort at the north end of Dingle Ridge Road.

Towns: Ridgefield, North Salem, Southeast.

Route: From center of Ridgefield, take Route 116 north into New York State; right on Route 121, past Peach Lake to old Route 6. Turn right and follow this four-lane but lightly used highway about one mile to Dingle Ridge Road on right. The first part of Dingle Ridge is steep, rising nearly 400 feet in elevation; if you're not an active cyclist, feel free to walk your bike up this part and enjoy the vistas to the right. Dingle Ridge, which soon turns to well-maintained dirt surface, heads south past stately horse farms and estates, wide fields, and woods. At first main intersection, bear left onto Vail Road, follow southward past Finch Road. Keep left again onto Norton Road. About a mile later, turn left onto Wallace Road, also dirt, which turns into Mopus Bridge Road in Ridgefield. Follow Mopus Bridge to first right (near its end) which will lead onto Ridgebury Road. Turn right on Ridgebury to three-way-stop intersection. Go straight across onto Ledges Road to its end; right on Barlow Mountain past Pierrepont State Park and pond, and Ridgefield Recreation Center. Left on North Street back to Route 116 in center of Ridgefield. Keep south onto Route 35, Main Street, to your starting point.

The Hamlets

About: 28 miles; rolling hills and flatlands. A trip through six upper Westchester hamlets that include many handsome houses. The journey also features many miles of wooded road, a beautiful reservoir, and attractive countryside.

Towns: Ridgefield, Lewisboro, Bedford, Pound Ridge, New Canaan.

Route: Take Route 35 west; soon after crossing New York line and passing traffic lights, look for Spring Street on right. Follow into hamlet of South Salem; just past Presbyterian Church, turn left to continue on Spring back onto Route 35; right on 35, through lights at Cross River, down hill to Route 121, left on 121 to Route 22 just north of Bedford Village; left on 22 into village, keeping left at the Green; take left onto Route 172 (Pound Ridge Road), follow nearly five miles to hamlet of Pound Ridge; following signs to Scotts Corners, turn right onto Route 137 about half mile to fork in road at intersection of Westchester Avenue and High Ridge Road (137); carefully bear left onto Westchester Avenue (sign says "to Route 124) and follow through commercial hamlet of Scotts Corners and into New Canaan, where road becomes Route 124; near top of a hill, bear left around island onto Luke's Wood Road; continue about a mile, turn left onto West Road which leads to Route 123 in hamlet of Vista; left onto 123 north to either Elmwood Road or West Lane (see Return Route 2 at end).

Urban Circle

About: 28 miles through some countryside, but also some urbanized sections of Bethel and Danbury, including a trip around Danbury Airport.

Towns: Ridgefield, Redding, Bethel, Danbury.

Route: From center of Ridgefield, take Route 102, Branchville Road, to Route 7; left on 7 about 2 miles to Simpaug Turnpike on right (at Walpole Woodworkers); follow north, jogging across railroad tracks, but following road as it parallels track; cross bridge and turn left immediately; at West Redding, pass post office on right and soon, left onto Sidecut Road to Route 53; left on 53 into Bethel; follow 53 into Danbury (South Street); at traffic light at intersection of South, Main Street and Rogers Park, right onto Main, follow past green into center of city; at traffic light by library, left onto West Street; continue through light at Deer Hill and watch for small triangular park on left; just past park, left onto Division Street to end at Wooster Village; right on West Wooster Street to stop sign, right to light at Park Avenue; left on Park Avenue; Park becomes Backus Avenue, passing the Danbury Fair Mall; straight through light at Kenosia Avenue; soon, left onto Miry Brook (almost oppose Wooster School); follow around the back of the airport; right onto Old Sugar Hollow Road, by small cemetery; right onto Route 7 south into Ridgefield to Route 35 and back into center of town.

New York Reservoirs

About: 28 miles; a couple of fair hills but mostly flat. Westchester is loaded with New York City reservoirs. This trip, using all state roads, takes you past two, the more scenic of which is the Titicus. You'll pass through about six miles of North Salem woods and pastures.

Towns: Ridgefield, Lewisboro, North Salem.

Route: Take Route 35 west to Route 22 at Katonah, passing the Cross River Reservoir on your left, about 10 miles; right (north) on 22 about five miles, right onto Route 116 alongside the Titicus Reservoir. Follow 116 back into Ridgefield to Route 35 in village.

Northern North Salem

About: 31 miles of rolling hills, a few steep. This journey offers plenty of scenic "back roads" through woods and fields, over good state highways and old dirt roads. Fields on Hardscrabble Road are great for birding-- stop by Outhouse Orchards for a refreshing apple.

Towns: Ridgefield, Lewisboro, North Salem.

Route: Take Route 35 west into New York State and follow to Cross River; at light, right onto Route 121; left onto Route 138 into Goldens Bridge; left before bridge, past shopping center, to Route 22; right onto 22; follow north through Purdys under I-684 to traffic light; turn right onto Hardscrabble Road, over I-684 and on past orchards and North Salem Vineyards winery; at end, left on June Road, right on Bloomer Road past golf courses to Route 121; dogleg across 121 to Dingle Ridge (between convenience store and liquor store) and, after a short distance, right on Finch Road; at intersection with Vail, Finch becomes dirt; follow into Connecticut, where it becomes Chestnut Hill Road and pavement returns; soon, right onto Spring Valley Road south to Ridgebury Road; right on Ridgebury to three-way-stop intersection. Go straight across onto Ledges Road to its end; right on Barlow Mountain past Pierrepont State Park and pond. Left on North Street which leads back to Route 116 in center of Ridgefield. Keep south onto Route 35, Main Street, to your starting point.

Scenic Saugatuck

About: 33 miles, much of it along the Saugatuck River and Reservoir. In fact, you follow the river till it becomes a reservoir, then pass right by the dam that creates the reservoir. Plenty of beautiful woods and some deep gorges, plus pretty countryside. In winter months, you may see bald eagles over the reservoir.

Towns: Ridgefield, Danbury, Redding, Weston, Wilton.

Route: From center, take 35 north to Route 7; left onto 7, cross into Danbury and a short distance later, take right onto new West Starrs Plain Road, left on Starrs Plain, right onto West Redding Road (at bridge) to Long Ridge Road; right on Long Ridge; cross tracks and bear left past shopping area to Side Cut Road to Route 53. Turn right and follow 53 about six miles, past the very scenic head of the Saugatuck Reservoir, a great place to stop and enjoy the view. About a half mile after entering Weston and near the top of a hill, watch for Valley Forge Road on left. This beautiful road skirts wooded and houseless edge of reservoir, past dam and through gorge. South to four-way intersection; go straight through two stop signs onto Lyons Plain Road to Route 57; right on 57, left at light onto Broad Street, left onto Newtown Turnpike, right at light onto Route 33 (Wilton Road). Follow 33 back to Ridgefield (see Return Route 1 for less hilly bypass of part of 33).

Six-Town Jaunt

About: 34 miles.

About: Variety of countryside, using both state and town roads, and even an unpaved bike trail through some woods near Wilton center. Some hills, none awful. Towns: Ridgefield, Danbury, Redding, Wilton, New Canaan, Lewisboro.

Route: From center, take 35 north to Route 7; left onto 7, cross into Danbury and a short distance later, take right onto West Starrs Plain Road, left on Starrs Plain, right onto West Redding Road (at bridge) to Long Ridge Road; right on Long Ridge; just after crossing tracks, right on Simpaug Turnpike; continue south on Simpaug about two miles to Route 7; follow 7 south to Georgetown, left on Route 107, right on Route 57; almost immediately after, turn right onto Main Street, which turns into Old Mill Road, then Mather Street, paralleling railroad tracks, south to Honey Hill, right to Route 7, left and south on 7 about 1.3 miles past Wilton High School to School Road (at light), turn right onto School Road, then bear left; on left, look for Bike Trail sign; follow trail through pretty woods; exit onto Lover's Lane at right, up hill past theater and Congregational Church to light at Route 33; cross 33 to Belden Hill Road (old Route 106) and continue south about 1.2 miles to stop sign; turn right onto Route 106 (New Canaan Road) and down long hill; 106 will jog left, then right, then left, then right -- watch signs closely. You'll end up at Route 123 in New Canaan. Right on 123 and north about 7 miles into Lewisboro (Vista), N.Y.; watch for West Lane on right; follow West Lane into Ridgefield to Route 35 (see return trip 2).

Country, sea and city scenes

About: 37 miles.

About: This pleasant ride takes you through rural countryside, a couple of villages, along the shore, and even through industrial South Norwalk. Towns: Ridgefield, Lewisboro, New Canaan, Darien, Norwalk, Westport, Wilton.

Route:  From fountain, take Route 35 (West Lane) west to Little Red Schoolhouse in triangle, bear left here to remain on West Lane but leave Route 35; continue on West Lane into New York; at third stop sign, turn left to stay on West Lane, to Route 123. Left on 123 to Vista Hamlet; at gas station at top of hill, turn right onto West Road; at end, right on Lukes Wood Road to Route 124; left on 124 to New Canaan village. At second light after firehouse (on left), continue straight onto Main Street which, in a mile or so, at four-way intersection, becomes White Oak Shade Road; cross over Merritt Parkway and soon turn right onto Brookside south to U.S. Route 1. Cross Route 1 and, at church, turn left onto Old Kings Highway (ancient predecessor of U.S. Route 1) and soon bear right onto bridge over I-95; continue on Old Kings, bear right onto Rowayton Avenue; after a mile or so, go under train bridge and in a few blocks, left at light into Rowayton harbor village. You are now on Route 136, which goes left off Rowayton Avenue onto McKinley Street by new bank. (For a short side trip, instead of turning, continue south on Rowayton a few blocks past restaurants, fish market, and boats, to small park, which has water fountain and benches overlooking Rowayton Harbor.) At top of McKinley, left on Highland to Wilson Avenue, right on Wilson; at bottom of hill, on left, note marsh -- large flocks of wild turkeys can often be seen here. At light, turn right to remain on 136 and Wilson Avenue through industrial section of South Norwalk. Wilson becomes Meadow; at end, left on Woodward, then very shortly, right on Burritt to stop sign; left on Water Street, north several blocks, then bear right over the lift bridge and past Veterans Park to first right onto Sea View Avenue which, at sharp curve, turns into First Street; right onto Cove Avenue, left on Fifth, then carefully straight through intersection and, very soon, bear right onto Calf Pasture Road. (At end is Calf Pasture Park -- free access to bicyclists year round, with lots of beaches and views; food and rest rooms in season.) Just before park, left onto Canfield, then left again to remain on Canfield past Shorehaven Golf Club; at top of hill, right onto Pine Hill to end; right on Old Saugatuck Road, which becomes Duck Pond Road. At end, right on Route 136, Saugatuck Avenue, which goes into Saugatuck section of Westport. Continue north under train bridge to Riverside and Route 1 in Westport center. Cross Route 1 onto Route 33 and follow Route 33 back to Ridgefield (see return trip 1).

Over Ponus Ridge

About: Here's a 37 mile journey through some beautiful countryside, including woods and a reservoir, and a bit of city outskirts. It takes you over Ponus Ridge, named for the Indian chief who sold early settlers much of the land that's now Stamford.

Towns: Ridgefield, Lewisboro, Pound Ridge, New Canaan, Stamford, Darien.

Route: Route 35 into New York; shortly beyond traffic lights, slant left onto Ridgefield Avenue; left onto Cross Pond Road, bearing left at first major intersection, until it ends at Route 124; left on 124 into Pound Ridge; left on Route 137, follow signs to Scotts Corners on Westchester Avenue; in center of Scotts Corners, by Shell gas station, right onto Trinity Pass; left onto Ponus Ridge (by top of Laurel Reservoir); Ponus Ridge runs 5 miles along the west border of New Canaan (watch for and read small monument to Indian Ponus at Davenport Ridge intersection); in Stamford, Ponus Ridge becomes Hope Street; follow south about 3 miles to light at Church Street; left onto Church; bear left as Church soon merges into Glenbrook; soon, right on Courtland (Route 106), and in two blocks, left onto Maple Tree Avenue, which brings you onto West Avenue in Darien; follow West Avenue (a posted bike route) to Route 1 by railroad overpass in center of Darien; turn left onto Route 1 and a short distance later, left onto Route 124 (Mansfield Avenue); follow 124 north into center of New Canaan; right on Maple, left on Main, right on East Avenue (or just follow signs to Route 123); at 123, take left and follow north to Ridgefield (see Return Route 2).

A Dip Down to Darien

About: Approximately 40 miles. Despite its length, this route has no "mean" hills and plenty of fine countryside and countless handsome homes.

Towns: Ridgefield, Lewisboro, Pound Ridge, New Canaan, Stamford, Darien.

Route: Take Route 35 west into New York State about 3.5 miles to left onto Route 124 to Pound Ridge; bear left at stop sign onto Route 137 and continue about quarter mile to fork; bear left toward Scotts Corners on Westchester Avenue (not 137) and continue south through commercial Scotts Corners hamlet and into New Canaan where road becomes Route 124. Continue south into New Canaan village; watch signs closely for right turn, then left to stay on 124, which becomes South Avenue. A short distance south of the village, right onto Route 106 about 4.5 miles. Just into Stamford, before 106 goes over railroad main line bridge, take left on Maple Tree Avenue, which becomes West Avenue and follow about 2.5 miles to Route 1 in Darien center. Here there are lots of places to stop for refreshment. Left on Route 1 for about one block, then left on Route 124 back to New Canaan village. Watching for signs to Route 123, take right on Maple, left on Main, right on East Avenue to 123; left on 123 (see return trip 2).

Newtown Turnpike Trek

About: 42 miles. Hilly at end. For those who are in fairly good shape. This trip includes wonderful samples of countryside in seven Connecticut towns. You will follow the route of the old Newtown Turnpike, a stagecoach route that connected Norwalk and Newtown. Parts today are well-paved state highway while other sections are dirt roads.

Towns: Ridgefield, Danbury, Redding, Bethel, Newtown, Weston, and Wilton.

Route: From center, take 35 north to Route 7; left onto 7, cross into Danbury and a short distance later, take right onto West Starrs Plain Road, left on Starrs Plain, right onto West Redding Road (at bridge) to Long Ridge Road; right on Long Ridge; cross tracks and bear left past shopping area to Side Cut Road to Route 53; left on 53 about 2 miles into Bethel, watch for Nashville Road on right; take Nashville into center of Bethel (bearing right at fork intersection after about .75 mile); turn right on Route 302 (Greenwood Avenue) and follow 302 into Newtown, about 4 miles. Right on Flat Swamp Road, right on Poverty Hollow. This is part of old Newtown Turnpike, which ran from Norwalk to Newtown; you'll follow turnpike about 16 miles altogether. To do that, turn right on Hopewell Road (part of the turnpike); until about 1996, this section was still a dirt road. Cross Route 58 onto Newtown Turnpike and follow south through scenic Redding countryside; it will turn into Route 53 at the pretty Saugatuck Reservoir. Follow 53 south till it meets Route 57 near Cobbs Mill Inn. At stop sign, note dirt road ahead but to right of Route 53 -- that's the continuation of Newtown Turnpike. Take that route south; it soon returns to pavement and follows a valley and comes out at Route 33 at Three Bears Inn. While turnpike continues south into Norwalk, you turn right on 33 and follow it to Route 7, follow 7 and 33 north to where 33 splits off to the left across railroad bridge. Take 33 north. Just after crossing into Ridgefield, watch for old gasoline station on right -- just before it, take right onto Wilton Road East and follow north about 1.5 miles till it rejoins Route 33 at Main Street, Ridgefield (see also return trip 1).

Nine-Town Trip

About: 43 miles. Rolling. Hills at end. A long but beautiful journey that includes pretty villages, handsome countryside, and a lonely dirt road.

Towns: Ridgefield, Danbury, Redding, Bethel, Easton, Fairfield, Westport, Weston, Wilton.

Route: Follow route of "Newtown Turnpike Trek" through Danbury, Redding, Bethel, and into Newtown. Once on Poverty Hollow, don't turn onto Hopewell, but continue south through beautiful valley. Route becomes Valley Road. Stay on Valley which turns to dirt through deep woods of Bridgeport Hydraulic Company. Woods have many wildflowers in spring. Swamp you'll cross is excellent birding spot. At crossroads, continue south on Valley in Easton till it comes out on Route 58. This section has signs noting it's an official scenic highway. Follow 58 to Route 136, turn right and follow along northern Fairfield about 4 miles into Westport to Coleytown Road, right onto Coleytown, merge onto Lyons Plain, right on Route 57 in Weston, left at light onto Broad Street, left onto Newtown Turnpike, right at light onto Route 33 (Wilton Road). Follow 33 back to Ridgefield (see Return Route 1 for less hilly bypass of part of 33).

A Pair of Cities

About: This 45 miler will take you from the wooded countryside, to the center of a big city, near the center of a medium city, and back into the countryside. Hills are all well-graded. It's best done on early on Sundays or holidays when traffic isn't too bad.

Towns: Ridgefield, Lewisboro, Pound Ridge, Stamford, Darien, Norwalk, New Canaan.

Route: Take Route 35 into New York to left on Route 124 to Pound Ridge; left onto Route 137 which becomes High Ridge Road and runs into Stamford. Continue south; about 2.5 miles after going under Merritt Parkway, you come to light at a multi-road intersection. Continue straight onto Summer Street; continue south to Main Street, which is U.S. Route 1. Follow Route 1 into scenic Darien and then Norwalk. In Norwalk Route 1 becomes Connecticut Avenue but, shortly after Norwalk Hospital (on left), it turns right under New Route 7 bridge. You, instead, stay straight on Riverside Avenue, which comes into Route 123. Go straight onto 123 and follow north back home (see Return Trip 2).

Southport and the Shore

About: Here's a 45 mile trip that includes rolling (but not outrageous) hills, an old seaport, harbors, some beaches, shoreline mansions, and a bit of the city of Norwalk.

Towns: Ridgefield, Weston, Westport, Fairfield, Norwalk, New Canaan, Lewisboro.

Route: From Ridgefield center, take Route 102, Branchville Road to Route 7; right on 7 to left on Route 107 a short distance to right on Route 53 into Weston; at stop near Cobb's Mill Inn, right onto Route 57 south through Weston into Westport; just after going under Merritt Parkway, look for fork in road and bear left at fork (actually, it's straight ahead) to stay on Weston Road (i.e., leave Route 57); left at end of Weston Road onto Cross Highway to four-way stop at North Street; right on North to end; left on Long Lots, right on Bulkley Avenue North to U.S. Route 1 (Post Road); left on Post Road into Fairfield; before I-95 overpass, look for Center Street on right; take Center under I-95 and under railroad bridge to Pequot Avenue; left a couple blocks into the village of Southport; right by food market onto Main Street to Harbor Avenue, right on Harbor, past park, then right on Westway back to Pequot; left on Pequot, which will lead past fine homes and to Southport Beach (where a bicyclist can stop and enjoy a rest on the sand; only cars need permits.); over small bridge and left, Pequot becomes Beachside Avenue which passes many mansions (Don Imus and Phil Donahue live along here); at intersection by swamp, cross over to road that goes up hill and over I-95 and train tracks; continue straight at stop sign as road merges with Greens Farms Road; continue on Greens Farms to stoplight at the Sherwood Island connector; straight across on Greens Farms to stop sign at Hills Point (alongside I-95); continue straight across onto bike lane and follow into Compo section of Westport, across bridge; left at light, then just after I-95 overpass, take right to Route 136 (Saugatuck Avenue). Left on 136 into Norwalk, where it becomes Winfield Street; at light at end of Winfield, right onto East Avenue; at intersection at lower end of Norwalk Green, head straight along right side of green to light at U.S. Route 1 (North Avenue); left onto Route 1 several blocks to Main Avenue (the old U.S. Route 7); right on Main Avenue and continue north to Route 123, a left at a three-way traffic light; cross tracks and follow 123 north to Ridgefield (see Return Trip 2).


Return trip 1

Return to Ridgefield from Wilton center area: These two options avoid some stiff hills at the upper end of Route 33 in Ridgefield. In the first, take 33 from Route 7 or Wilton Center about 3 miles north to Vista Road on left (just beyond firehouse). Near its end, it turns to dirt. At end, turn right onto Silver Spring Road, also dirt, and follow it north into Ridgefield to Route 35 by the Little Red School house. Bear right on 35 into Ridgefield center. The second option is to continue on Route 33 into Ridgefield and, just before the abandoned gas station, bear right onto Wilton Road East and follow this north until it reconnects with Route 33 at the south end of Main Street near Ridgefield center. This is a steady, comfortable grade.

Return trip 2

Return to Ridgefield from New Canaan area: One of the easiest approaches to Ridgefield from the south is Route 123, which starts in Norwalk and ends in New York state at Route 35. The inclines are the smoothest of any state road heading north and, in Connecticut at least, the shoulders are wide. Once into New York State on 123, you have two choices for return routes. Just above Vista about a quarter mile, Elmwood Road forks off to the right. This road parallels 123. It's a bit less smooth and a bit more hilly, but it also has a 30 mph speed limit and much less traffic. Route 123, on the other hand, has a smoother surface and very gradual grades. Try both and see which you like. On Route 123, West Lane will be a right about 2.5 miles north of Vista. Elmwood ends at West Lane; turn right. Follow West Lane eastward to Route 35, right on 35 into Ridgefield village.


Cycling Books

For more trips in this area, check your favorite book store for the following:


20 Bicycle Trips in central Fairfield County and Northeastern Westchester Centered on Ridgefield, Conn. was compiled by Jack Sanders. If you'd like to comment, suggest a good trip, or offer an update or correction, please write Jack Sanders, 91 Olmstead Lane, Ridgefield, CT., 06877. E-mail: jackfsanders@gmail.com

Copyright 1996-2007 Jack Sanders,

Last Revised Sept. 14, 2007

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