Prospect Trails and Maps

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Find the top rated trails in Prospect, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
44 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

55.9 mi
State: CT
Gravel

Billings Trail

3.3 mi
State: CT
Dirt

Branford Trolley Trail

0.5 mi
State: CT
Concrete, Crushed Stone, Gravel

Briarcliff-Peekskill Trailway

12 mi
State: NY
Asphalt, Dirt, Grass

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Charter Oak Greenway

11.1 mi
State: CT
Asphalt

Cheney Rail Trail

1 mi
State: CT
Crushed Stone

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Derby Greenway

1.85 mi
State: CT
Asphalt

Farmington Canal Heritage Trail

40 mi
State: CT
Asphalt, Cinder, Crushed Stone, Grass, Gravel

Farmington River Trail

14.9 mi
State: CT
Asphalt, Cinder, Crushed Stone, Dirt

Harlem Valley Rail Trail

17.3 mi
State: NY
Asphalt, Crushed Stone

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kennedy Trail

1.7 mi
State: NY
Cinder

Kings Park Hike & Bike Trail

1.5 mi
State: NY
Asphalt

Kress Family Trail

2.5 mi
State: CT
Dirt

Larkin State Park Trail

10.4 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel
Accordion

Maybrook Trailway

3.7 mi
State: NY
Asphalt

Middlebury Greenway

4.4 mi
State: CT
Asphalt

Naugatuck River Greenway

5.4 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

North County Trailway

22.1 mi
State: NY
Asphalt

Norwalk River Valley Trail

5.8 mi
State: CT
Asphalt

Old Croton Aqueduct Trail

22.8 mi
State: NY
Asphalt, Concrete, Dirt

Old Mine Railroad Trail

2.2 mi
State: NY
Dirt

Pequonnock River Trail

12.8 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.55 mi
State: NY
Asphalt

Quarry Trail

0.1 mi
State: NY
Dirt, Grass

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Ridgefield Rail Trail

2.3 mi
State: CT
Gravel

Savin Rock Trail

1.2 mi
State: CT
Asphalt, Concrete

Shoreline Greenway Trail

2.3 mi
State: CT
Crushed Stone

Southwick Rail Trail

7.1 mi
State: MA
Asphalt

Stratton Brook State Park Trail

1.2 mi
State: CT
Asphalt, Cinder, Crushed Stone

Sue Grossman Still River Greenway

2.9 mi
State: CT
Asphalt

Trolley Trail (CT)

0.75 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...
CT 55.9 mi Gravel
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...
CT 0.5 mi Concrete, Crushed Stone, Gravel
The Briarcliff-Peekskill Trailway is a 12-mile linear park that runs from the town of Ossining north to Westchester County's Blue Mountain Reservation in Peekskill. The trail is built on land...
NY 12 mi Asphalt, Dirt, Grass
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for 11 miles between Bolton and downtown Hartford, though there is currently...
CT 11.1 mi Asphalt
The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...
CT 1 mi Crushed Stone
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
MA 0.21 mi Asphalt
Columbia Greenway Rail Trail offers 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts, from Main st, across the Great River Bridge over the Little River to the...
MA 2 mi Asphalt
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
MA 5.4 mi Asphalt
The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...
CT 1.85 mi Asphalt
The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...
NY 8.5 mi Asphalt
Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...
CT 40 mi Asphalt, Cinder, Crushed Stone, Grass, Gravel
The Farmington River Trail is built upon the former Central New England Railroad corridor and runs between the Farmington Canal Heritage Trail near Tunxis Meade Park and the Simsbury town line. A...
CT 14.9 mi Asphalt, Cinder, Crushed Stone, Dirt
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
NY 17.3 mi Asphalt, Crushed Stone
The Hop River State Park Trail is one of Connecticut's longest rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Near its western end is the Charter Oak...
CT 20 mi Crushed Stone
The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...
NY 1.7 mi Cinder
The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...
NY 1.5 mi Asphalt
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...
CT 2.5 mi Dirt
Canopied with deciduous trees for most of its 10.4 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
CT 10.4 mi Cinder, Crushed Stone, Dirt, Gravel
Accordion
Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...
NY 3.7 mi Asphalt
The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
CT 4.4 mi Asphalt
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
CT 5.4 mi Asphalt
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...
NY 22.1 mi Asphalt
When completed, the Norwalk River Valley Trail will run from Danbury to Long Island Sound in southwestern Connecticut, for a total of about 27 miles. Currently, several disconnected sections totaling...
CT 5.8 mi Asphalt
The Old Croton Aqueduct State Historic Park follows the route of the Old Croton Aqueduct, which carried water to New York City from 1842 to 1955. Most of the structure lies beneath the trail and has...
NY 22.8 mi Asphalt, Concrete, Dirt
Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...
NY 2.2 mi Dirt
The Pequonnock River Trail—portions of which are also known as the Housatonic Railway Rails to Trails, Monroe Housatonic Railbed Trail and Pequonnock Valley Greenway—is a developing system stretching...
CT 12.8 mi Asphalt, Crushed Stone
The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...
NY 11.55 mi Asphalt
The Quarry Trail is currently a 600-foot long unimproved strip of land along what is known as Quarry Road in the Village of Hastings-on-Hudson, NY. The trail links Old Croton Aqueduct State Historic...
NY 0.1 mi Dirt, Grass
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
MA 1.4 mi Asphalt
The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...
CT 2.3 mi Gravel
The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...
CT 1.2 mi Asphalt, Concrete
The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...
NY 3.4 mi Asphalt
When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...
CT 2.3 mi Crushed Stone
The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...
MA 7.1 mi Asphalt
The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...
CT 1.2 mi Asphalt, Cinder, Crushed Stone
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...
CT 2.9 mi Asphalt
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
CT 0.75 mi Asphalt
Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...
CT 4 mi Crushed Stone
The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...
NY 13 mi Asphalt
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30."  The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...
CT 4.5 mi Asphalt

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Trails by activity

Billings Trail

CT - 3.3 miles

Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...

Columbia Greenway Rail Trail

MA - 2 miles

Columbia Greenway Rail Trail offers 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts, from Main st, across the Great River Bridge over the Little River to the...

Derby Greenway

CT - 1.85 miles

The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...

Setauket-Port Jefferson Station Greenway Trail

NY - 3.4 miles

The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...

Accordion

CTfastrak Multi-Use Trail

CT - 4.4 miles

A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...

William R. Steinhaus Dutchess Rail Trail

NY - 13 miles

The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...

Kings Park Hike & Bike Trail

NY - 1.5 miles

The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...

Charter Oak Greenway

CT - 11.1 miles

The Charter Oak Greenway is a paved, multi-use trail connecting parks with residential and commercial areas. The trail runs for 11 miles between Bolton and downtown Hartford, though there is currently...

North County Trailway

NY - 22.1 miles

The North County Trailway is the longest of the four connected rail-trails breathing new life into the former New York Central Railroad's Putnam Division line. The "Old Put" provided passenger and...

Cheney Rail Trail

CT - 1 miles

The Cheney Rail Trail follows part of the corridor of the South Manchester Railroad, built by the Cheney brothers in 1869. The line was a 2.5-mile spur from the main Hartford, Providence, and Fishkill...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Southwick Rail Trail

MA - 7.1 miles

The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

CT - 4.5 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk March 1–November 30."  The 4.5-mile Windsor Locks Canal Trail follows the Connecticut River and the Windsor Locks...

Railroad Ramble

CT - 1.7 miles

The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...

Savin Rock Trail

CT - 1.2 miles

The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...

Air Line State Park Trail

CT - 55.9 miles

Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...

Sue Grossman Still River Greenway

CT - 2.9 miles

The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...

Shoreline Greenway Trail

CT - 2.3 miles

When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Harlem Valley Rail Trail

NY - 17.3 miles

Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...

EPCAL Alternative Transportation Path

NY - 8.5 miles

The EPCAL Alternative Transportation Path loops around the 2,900-acre Enterprise Park at Calverton (hence its name: EPCAL) on New York’s Long Island and links to the Town of Riverhead’s 65-acre...

Hop River State Park Trail

CT - 20 miles

The Hop River State Park Trail is one of Connecticut's longest rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Near its western end is the Charter Oak...

Sue Grossman Still River Greenway

CT - 2.9 miles

The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...

Air Line State Park Trail

CT - 55.9 miles

Air Line State Park Trail winds for just over 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. Over the state...

Accordion

Putnam Trailway

NY - 11.55 miles

The final passenger cars of the Putnam Division of the New York Central Railroad ran in 1958, but the rail line that so influenced development of this area still sparks nostalgia. The "Old Put"...

Old Mine Railroad Trail

NY - 2.2 miles

Fahnestock State Park is a relatively undiscovered gems in the New York State Park System. Located a few miles east of Cold Spring Village on Rt. 301 (Main Street), the park jurisdiction was recently...

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Setauket-Port Jefferson Station Greenway Trail

NY - 3.4 miles

The Setauket-Port Jefferson Station Greenway Trail stretches just over 3 miles along Long Island’s north shore. Construction was completed in two phases with the first trail section opening in 2009...

Chicopee River Canal Rail Trail

MA - 0.21 miles

The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...

Ridgefield Rail Trail

CT - 2.3 miles

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

CTfastrak Multi-Use Trail

CT - 4.4 miles

A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...

Branford Trolley Trail

CT - 0.5 miles

The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...

Harlem Valley Rail Trail

NY - 17.3 miles

Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...

Middlebury Greenway

CT - 4.4 miles

The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Kennedy Trail

NY - 1.7 miles

The Kennedy Trail begins at the northwest corner of the 68-acre campus of John F. Kennedy Catholic High School in Somers. The town, which sits 30 miles from White Plains and 55 miles from New York...

Southwick Rail Trail

MA - 7.1 miles

The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...

Savin Rock Trail

CT - 1.2 miles

The Savin Rock Trail offers just over a mile of paved pathway along West Haven’s coastline. Along the way, you’ll enjoy picturesque views of Long Island Sound and access to its sandy beaches. The west...

Shoreline Greenway Trail

CT - 2.3 miles

When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Kings Park Hike & Bike Trail

NY - 1.5 miles

The Kings Park Hike & Bike Trail runs for 1.5 miles between Old Dock Road at Church Street in Kings Park and Nissequogue River State Park. The trail is a town of Smithtown park and follows an...

Redstone Rail Trail

MA - 1.4 miles

The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...

Maybrook Trailway

NY - 3.7 miles

Owned by the Metro-North Railroad, the Maybrook Trailway starts at the Connecticut state line in Farringtons Park, and spans 5 miles into the town of Brewster. The trail follows what was once part of...

Ridgefield Rail Trail

CT - 2.3 miles

The Ridgefield Rail-Trail meanders for nearly 2.5 miles through the forested exburbs of Ridgefield, Connecticut. The trail passes among suburban acreages, along a creek at one point, and past a couple...

Shoreline Greenway Trail

CT - 2.3 miles

When complete, Connecticut's Shoreline Greenway Trail will be a scenic 25-mile route through four quaint New England towns off Long Island Sound. From Lighthouse Point to Hammonasset Beach State Park,...

Accordion

Kress Family Trail

CT - 2.5 miles

The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, 2.5-mile trail is popular with cross-country skiers and snowshoers in...

Southwick Rail Trail

MA - 7.1 miles

The Southwick Rail Trail is now complete from the Massachusetts–Connecticut state line, where it continues south as the Farmington Canal Heritage Trail. On the north end, the trail extends to the...

Branford Trolley Trail

CT - 0.5 miles

The Branford Trolley Trail is essentially a long footbridge occupying an old bridge along the route of an abandoned trolley track. The bridge links nature trails on both sides of the water through a...

Farmington Canal Heritage Trail

CT - 40 miles

Running north from the Yale University campus in New Haven through the heart of Connecticut, the multi-use Farmington Canal Heritage Trail, when completed will stretch uninterrupted more than 80 miles...

Naugatuck River Greenway

CT - 5.4 miles

The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...

Connecticut Riverwalk and Bikeway

MA - 5.4 miles

The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...

Vernon Rails-to-Trails (Hop River State Park Rockville Spur)

CT - 4 miles

Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...

Trolley Trail (CT)

CT - 0.75 miles

The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...

Harlem Valley Rail Trail

NY - 17.3 miles

Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...

William R. Steinhaus Dutchess Rail Trail

NY - 13 miles

The Dutchess Rail Trail is a local treasure in the Hudson Valley region of New York, and for good reason: the 13-mile trail runs through what seems like a perpetually green landscape of dense tree...

Chicopee River Canal Rail Trail

MA - 0.21 miles

The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...

Hop River State Park Trail

CT - 20 miles

The Hop River State Park Trail is one of Connecticut's longest rail-trails. Narrow cuts and a lush tree canopy make for enjoyable visits year-round. Near its western end is the Charter Oak...

Derby Greenway

CT - 1.85 miles

The Derby Greenway runs between Division Street and Main Street, paralleling the Naugatuck and Housatonic rivers. The trail runs on top of a flood control dyke for the rivers; a portion of it goes...

Middlebury Greenway

CT - 4.4 miles

The delightful asphalt Middlebury Greenway winds 4.4 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...

Stratton Brook State Park Trail

CT - 1.2 miles

The Stratton Brook State Park Trail presents a great way to work up an appetite for a picnic at Stratton Brook State Park, the first state park in Connecticut to be entirely wheelchair accessible. The...

New Milford River Trail

CT - 5 miles

The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....

Recent Trail Reviews

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

Bumpy but nice ride by river

August, 2017 by smithsr

As others mentioned a little bumpy from roots. Parking on south end is just beyond an old factory building. Turn down single lane road just before canal. There looks to be a gate across the trail, but there is a bike opening to the right. North end has nicer parking in a small park. Some historical info about canal in park. Trail continues north beyond park. Not sure how far it goes.

North County Trailway

Not Like It Used To Be

August, 2017 by bjohn435

The North County Trail is suffering from serious neglect. It used to be a well maintained, smooth riding experience. It is now in danger of becoming a Civil War era corduroy road. There are many areas that are in desperate need of re-paving. There is also a section that was eroded during Super Storm Sandy and has not been repaired. It's a shame that what was once a terrific trail has been allowed to degrade so much.

Pequonnock River Trail

broken trail

August, 2017 by timuze

This trail has a little bit of everything ..... asphalt, grass, hard packed dirt or gravel. We started on the North end at Pepper went south and was for the most part going on a slight downhill 80% of the way to The Trumbull trail end. It was for the most part lovely. Often very wide and smooth. I would go the opposite way as Linda and I always prefer to glide back to the car.

Accordion

Farmington Canal Heritage Trail

Farmington Canal Rail Trail (New Section) (NW Dr to Red Oak Hill Rd)

July, 2017 by russccc

Hi All,

They recently put the steel in place for the bridge over CT RT 6 in Farmington for Farmington Canal Rail Trail (FCRT). The section maybe in the maybe done in the fall of 2017? It should be complete rather fast! I scouted it out via car lots of this section done.
Trails, Russ C (tn) "Zenith"

Southwick Rail Trail

Southwick Rail Trail

July, 2017 by russccc

Hi All,
Someone asked where is H2~O??
The WATER FOUNTAIN is just due south of jct Southwick Rail Trail & Sam West Rd. Approximately 5.16 Miles North of the CT/MA Border. The fountain is probably seasonal. Nice Ride From CT Border to Main St Westfield, MA (Shop & Shop) Great Day & Good Time. Execellent Bike Pump & Repair Station at CT Quarry Rd & Phelps Rd Lot. Happy Trails, Russ C (tn) "Zenith"

Hop River State Park Trail

Riding the Hop River Trail

July, 2017 by furboy

We had two cars, and wanted to ride one way so we left one car behind the First Congregational Church 359 US 6, Andover, CT. The second car we parked at the trailhead 175 Colonial Rd, Manchester, CT where there is a dedicated parking lot. By car it was 15 minutes driving time one way between locations. From our start point we crossed RT 6 in front of the church to pick up the trail and then rode to the right heading west. The first 5 miles were a definite uphill grade, around mile 6 it became a downhill grade all the way to Manchester. Total distance between the two locations approximately 12 miles. Considering the trail is mostly hard packed dirt it was very well maintained, wider in some areas than others with a few road crossings. The scenery was mostly rocks that had been blasted through back when the railroad was built with a lot of ferns and greenery, but never saw the Hop River. There were mostly bikers on the trail, and everyone was very friendly. Other than the uphill grade for 5 miles it was a very pleasant ride. If you're looking for a nearby place to stay I highly recommended the Daniel Rust House in Coventry which was only 12 minutes from the church by car.

Farmington Canal Heritage Trail

Best of Connecticut

July, 2017 by nimmorp01

Started in Hamdon and road to Southington. Round trip was 28.04 miles. Rented bicycles from Cheshire bike shop which was all of 50 feet from trail. Trail was nicely paved the entire way except for a very short detour.

New Milford River Trail

Access way a little rough

July, 2017 by linda.gaboardi

Once you get in the main trail, it's a nice, easy ride. But I picked up some kind of metal shard in my tire, and I suspect it was on the access trail that starts on Boardman.

Windsor Locks Canal State Park Trail (WIndsor Locks Canal Towpath)

Beautiful but rough

July, 2017 by aswinsor

Beautiful ride along the river BUT you better have a very soft seat to absorb the rough surface!!

New Milford River Trail

Mostly Along River Road

July, 2017 by pbcibc

This is a nice place to stretch one's legs for about five miles. The southern end (just over Boardman Bridge from Route 7), with limited parking, runs through a town park for about 1.5 miles; the northern portion, ending at Gaylordsville, is just walking along the Housatonic on River Road, one of the few remaining dirt roads in the area. There is more parking at the park's main entrance off of River Road, about 1.5 miles north of Boardman Bridge.
If you like a flat trail in quiet woods and don't mind a few cars coming along, this is a pleasant way to spend a couple of hours. "There and back again" is about ten miles.

Maybrook Trailway

Short but Sweet for a Mountain Biker

July, 2017 by jrjets08

Paved ends at Griffin rd. Bridge, but Black fence ends at Pumphouse rd...Hoping it goes further,Then i go east and it ends at the Train Tressel which i understand because it would cost to much to cross it i guess,but then the cutoff is at at Lisi's towing which baffles me but when i drive down Rt.6 in my Vehicle the Black Fence starts up again Hmmm!!!.

Derby Greenway

Meh.

July, 2017 by nyjenniferc

Full of goose crap. Loud and noisy. Thought it would be serene and picturesque by the river, but it was really industrial and boring, with no shade. The parking lot in Derby sucks. The bridge in Derby was full of firework debris, paper and junk. Very disappointed.

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