Biking paths are numerous in New Haven Connecticut

Derby Greenway

Division Street to Main Street Derby, CT

Trail Length: 1.7 miles

The trail, which is 1.7 miles long, runs atop the flood control walls on the Naugatuck and Housatonic Rivers and is tied together by the portion of the trail running on O'Sullivan's Island. The trail links Derby to Ansonia and Shelton and also links the six major bridges in Derby. One of the centerpieces of the trail is the spectacular new pedestrian footbridge.
Trail Surfaces: Asphalt
Trail Activities: Bike, inline skating, wheelchair accessible, walking

Farmington Canal Heritage Trail

New Haven through Farmington to Massachusetts border,

Trail Length: 40 miles

Running north from the Yale University campus in New Haven through the heart of Connecticut, the Farmington Canal Heritage Trail comprises several distinct segments totaling 40 miles of rail-trail. The trail follows the corridor of the defunct Farmington Canal.

New Haven section. The trail's southern terminus is Yale's new Malone Engineering Building. The start of the trail is a 1.25-mile urban path. There is no designated trail parking, but on-street or garage parking is available. Starr Street marks the trail's end. To continue to the Hamden to Cheshire section, riders need to travel 4 miles on lightly trafficked roads. Turn right on Starr, travel one block, turn left on Newhall Street, and continue about a mile through the Putnam Avenue intersection; Newhall becomes Leeder Hill Drive. Follow Leeder Hill to Treadwell Street, take a right, then take an immediate left on Martin Terrace. At the road's end, turn left on Mather Street, followed by a right on Waite Street. Take the first left on Coram Street, then left again on Beverly Road. Follow Beverly around, then bear right on Woodbine Street. Make the third left on Elgin Street, go one block, then continue straight on Connolly Parkway. At Wilbur Cross Parkway (State Route 15), turn right to pick up the Hamden to Cheshire section.

Hamden to Cheshire section. A prominent sign for the New Haven & Northampton Railroad Canal Line marks the trailhead of this northbound segment at the Connolly Parkway in Hamden. Approaching Cheshire, you'll reach Lock 12 and keeper's house, now a historical park. Here you'll find trailhead parking, picnic tables, toilets, a drinking fountain, and a phone. Trail's end lies 1.6 miles north at a parking lot on Cornwall Avenue in Cheshire.

Southington section. From a trailhead parking area on West Main Street in downtown Southington, this 2-mile asphalt trail bridges the Quinnipiac River and passes through the heart of a restored mill section starting at Center Street. From here, turn right on Center Street and continue north to the trail's end on Hart Street.

Farmington to the Massachusetts border section. The 22-mile northern section of the Farmington Canal Heritage Trail shares its Tunxis Meade Park trailhead with the 8.5-mile Farmington River Trail. Within the first mile, you will cross a high bridge over the Farmington River. The trail first leaves the corridor 5.8 miles along in Avon, meandering a mile along surface streets and beneath Route 44 before rejoining the corridor at Sperry Park. Continue north through East Granby. Reaching a small bridge on Route 10, briefly follow the sidewalk, then turn right on Drake Hill Road and look for the trailhead to the right of Iron Horse Boulevard; turn left here to rejoin the corridor.
The trail continues north, paralleling the boulevard and passing Drake Hill Road Park. The trail continues 4 miles to a major break at Wolcott Road. From here, you can either backtrack to the closest trailhead at Route 315 or continue to the border. At Wolcott Road, turn right and travel a mile to a three-way intersection. Take another right, go about 100 yards, and turn left on Route 189. The trailhead lies a mile down this road on your right. From here, the trail continues 4 miles to the Massachusetts border.

Parking and Trail Access:
To reach the southern trailhead on the Yale campus, take Interstate 91 to Exit 3/Trumbull Street. Drive straight on Trumbull for three blocks to Hillhouse Avenue and look for on-street or garage parking. On weekends and after 4:30 p.m. on weekdays, Yale’s parking lots are open to the public for free.
To reach the Cheshire trailhead, take Interstate 691 to Exit 3 and head south on State Route 10/Highland Avenue through town. Turn right on Cornwall Avenue and proceed to the trailhead and adjacent parking. To drive to the southern access point, leave Route 15 (Wilbur Cross Parkway) at Exit 60 and drive north on Route 10 (Dixwell Avenue) for a quarter mile. Take the first entrance to the mall on your right and proceed to the large parking lot on the south side of the mall, which is adjacent to the trail.
To reach the West Main Street trailhead, take Interstate 691 to Exit 3 and head north on State Route 10/South Main Street to West Main. Turn left on West Main and proceed to the trailhead parking area.
To reach the southern trailhead in Farmington, take Interstate 84 to Exit 38 (from the south) or Exit 39 (from the north). Once in town, drive a mile west of Route 10 on Meadow Road to Tunxis Meade Park.
To reach the State Route 315 trailhead, take I-84 to Exit 38 (from the south) or 39 (from the north). Once in Farmington, head north on Route 10 through Avon and Simsbury. The Route 315 trailhead parking area lies 2 miles beyond the Iron Horse Boulevard trailhead.