Wallingford Trails and Maps

Looking for the best trails around Wallingford?

Find the top rated trails in Wallingford, 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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  • Length
Activities
Length
Surfaces
Type
41 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

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Charter Oak Greenway

11.1 mi
State: CT
Asphalt
Accordion

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

Maybrook Trailway

3.7 mi
State: NY
Asphalt

Middlebury Greenway

4.4 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 Mine Railroad Trail

2.2 mi
State: NY
Dirt

Pequonnock River Trail

12.8 mi
State: CT
Asphalt, Crushed Stone

Putnam Trailway

11.9 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 border, ...
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 the ...
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 marsh ...
CT 0.5 mi Concrete, Crushed Stone, Gravel
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 paved ...
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 is ...
MA 0.21 mi Asphalt
Accordion
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 Southwick ...
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 Bridge ...
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 across ...
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 recreational ...
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 short ...
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 being ...
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 Greenway, ...
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 City, ...
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 abandoned ...
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 winter, ...
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 residential ...
CT 10.4 mi Cinder, Crushed Stone, Dirt, Gravel
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 the ...
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 off-road ...
CT 4.4 mi Asphalt
The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer ...
CT 0.3 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. Thanks ...
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 freight ...
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 nearly ...
CT 5.8 mi Asphalt
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 expanded ...
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 from ...
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" carried ...
NY 11.9 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 Park ...
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 the ...
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 red ...
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 and ...
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 Westfield ...
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 York, ...
CT 2.9 mi Asphalt
...
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 and ...
CT 4 mi Crushed Stone
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 Canal ...
CT 4.5 mi Asphalt

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Trails by activity

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 border, ...

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 the ...

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 paved ...

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 ...

Accordion

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 ...

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 ...

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 is ...

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 Southwick ...

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 Bridge ...

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 across ...

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 recreational ...

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 ...

Farmington River Trail

CT - 14.9 miles

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 short ...

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 being ...

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 Greenway, ...

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 abandoned ...

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 the ...

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 off-road ...

Naugatuck River Greenway (Beacon Falls)

CT - 0.3 miles

The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer ...

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. Thanks ...

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 freight ...

Norwalk River Valley Trail

CT - 5.8 miles

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 nearly ...

Pequonnock River Trail

CT - 12.8 miles

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 from ...

Putnam Trailway

NY - 11.9 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" carried ...

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 the ...

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 red ...

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 ...

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 and ...

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, ...

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 Westfield ...

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 ...

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 York, ...

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 and ...

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 Canal ...

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 border, ...

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 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 marsh ...

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 paved ...

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 paved ...

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 ...

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 ...

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 is ...

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 Southwick ...

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 Bridge ...

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 across ...

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 recreational ...

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 ...

Farmington River Trail

CT - 14.9 miles

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 short ...

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 being ...

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 Greenway, ...

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 City, ...

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 abandoned ...

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 winter, ...

Larkin State Park Trail

CT - 10.4 miles

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 residential ...

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 the ...

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 off-road ...

Naugatuck River Greenway (Beacon Falls)

CT - 0.3 miles

The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer ...

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. Thanks ...

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 freight ...

Norwalk River Valley Trail

CT - 5.8 miles

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 nearly ...

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 expanded ...

Pequonnock River Trail

CT - 12.8 miles

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 from ...

Putnam Trailway

NY - 11.9 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" carried ...

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 the ...

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 red ...

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 ...

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 ...

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 and ...

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, ...

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 Westfield ...

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 ...

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 York, ...

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 and ...

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 Canal ...

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 border, ...

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 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 marsh ...

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 paved ...

Accordion

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 ...

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 ...

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 is ...

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 Southwick ...

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 Bridge ...

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 across ...

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 recreational ...

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 ...

Farmington River Trail

CT - 14.9 miles

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 short ...

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 being ...

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 Greenway, ...

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 City, ...

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 abandoned ...

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 winter, ...

Larkin State Park Trail

CT - 10.4 miles

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 residential ...

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 the ...

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 off-road ...

Naugatuck River Greenway (Beacon Falls)

CT - 0.3 miles

The Naugatuck River Greenway segment in Beacon Falls offers a short, but scenic route along the river that is paved and well-lighted. Just north of the trail's end at the Depot Street Bridge, lies Volunteer ...

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. Thanks ...

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 freight ...

Norwalk River Valley Trail

CT - 5.8 miles

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 nearly ...

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 expanded ...

Pequonnock River Trail

CT - 12.8 miles

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 from ...

Putnam Trailway

NY - 11.9 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" carried ...

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 the ...

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 red ...

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 ...

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 ...

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 and ...

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, ...

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 Westfield ...

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 ...

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 York, ...

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 and ...

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 Canal ...

Recent Trail Reviews

Farmington Canal Heritage Trail

Great ride!

May, 2017 by wilsonk9alex

Took my brand new bicycle on its maiden voyage on this trail. It was great fun. Rode for about 3 hours and loved every minute of it. The historic information posted along the trail is nicely done. The fact that there are restrooms at the trail head is fantastic! They really did a nice job with this trail. Highly recommend it for all. Very kid friendly.

Harlem Valley Rail Trail

Nice! As every trail should be.

April, 2017 by lughnerson

I travel far and wide to get to almost any bike trail, paved or not. This one is asphalt and pretty nice. Starting in Millerton near the refurbished rail station, I went south to Wassaic, end of the line where a noisy, fuel-smelling, working train station is the final stop. (I think there are bathrooms inside.) It is kind of a nice juxtaposition from the trail and village starting point. As described above, the rail trail goes through lovely rural county. A few root-bumps here and there, but nothing terrible. When the northern section has enough miles connected to make it worth my hour+ drive, I will give another review.

Millerton is a lovely village. If you like tea, check out Harney's tea shop, a small cafe, gift shop and tasting room.

Air Line State Park Trail

Airline Trail South

April, 2017 by CW4

Trail Report - The section of the Airline Trail from the dirt parking lot on Route 149 to the Blackledge River is currently under construction, about 1and 1/2 miles. You can ride east but not to the west due the resurfacing work.

New Extension Route 196 in East Hampton to Alden's Crossing (1.6 miles), is about 1/2 done. It has the gravel bedding in place but not the stone dust riding surface. The drainage design is poor and there are 4 large wet areas and erosion spots. It is ride-able but not too scenic or any fun.

Accordion

Putnam Trailway

Worth the Trip to Get There

April, 2017 by lughnerson

I go far distances and other states to spend time exploring different bike trails. It took my a little more than hour to visit the Putnam Rail Trail. This was the hilliest ride outside of mountain biking that I have done, yet the scenery was superb. Lots of lakes and reservoirs. Despite the 95-degree heat it was my favorite bike ride last year.

North County Trailway

Good ride

April, 2017 by sschwinn

I rode (using my cyclocross bike) this trail today end-to-end in conjunction with the Putnam Trail to make a 62+ mile out and back ride.
Overall the trail is in fairly good shape with somewhat tricky start/end points as noted in the previous review. As there is really no parking at the southern end I parked in a commuter lot just off the Saw Mill parkway about 2 miles from the south end and backtracked to complete the end-to-end.
While a road bike could be used for this trail I suggest a hybrid or cyclocross bike due to some tough pavement in spots and pretty heavy debris on the two on-road sections. The Putnam Trail is fine for a road bike.

Putnam Trailway

Putnam Trailway

April, 2017 by sschwinn

I rode this trail from end-to-end today in conjunction with the North County Trail. The trail is in very good shape. Fine for road bikes. It appears the new extension at the northern end is almost complete. the junkyard near the northern terminus was a nice touch!

Pequonnock River Trail

Bridge over parkway

April, 2017 by jmumper1

Work has begun to connect the Bridgeport section of the trail which ends at the north end of Quarry Road, over the Merrit Parkway to Rocky Hill Road in Trumbull. Progress can be seen from the ramps connecting RT-15 to RT25.

Maybrook Trailway

Great section running only still.......3.4 miles

April, 2017 by 10509.brewster

Paved section enter off N. Main St behind Kobackers to Peaceable Hill Rd. Run down the stairs around the corner on Rt 6 up the hill towards Brewster Honda back up the steps and continue to dead end/turnaround by Exit 10 ramp close to Danbury border. Combined with the local roads for a great run! Once the section is paved over the railroad bridge over RT 6/202 it will be a straight run, no stairs.

Derby Greenway

Best for walking, not biking.

February, 2017 by shortgal

The trail is not very wide (fits about four people across) and not really long enough for a decent bike ride. Best suited to walking. As others have said there are a lot of sections that are not shaded.

If you want a longer walk you can cross Division St and walk a section that was added on the Ansonia side. There are a few short inclines, most of the trail is flat.

Pequonnock River Trail

Nice winter scenery

January, 2017 by slipsoup

Unfortunately our ride on this trail was cut short due to the weather, combined with having to ride on the road. We started in Bridgeport near Glenwood Park. There was parking on the street near the start of the trail on Crown Rd. I'd suggest skipping the first segment of the trail that "starts" near the Bridgeport Transportation Center. This part is basically a brief road ride through a not so nice section of the city. The ride through Glenwood Park is nice, as it flanks the river. To continue to Twin Brooks Park and the continuation of the trail, you have to go left on Route 127 (White Plains Rd.). You can access Route 127 to the right, past a metal gate, just after passing remnants of a stone structure. If you bear left after this structure, you'll cross a bridge over the river to a parking lot. We look forward to returning to ride the rest.

Farmington Canal Heritage Trail

Southington-Farmington Construction Updates

December, 2016 by martinip

With the southern section nearly continuous from New Haven to Southington (minus the West Main Street-Cornwall Avenue gap in Cheshire), the next major gap is Plainville and its surroundings. The Curtiss Street-Lazy Lane segment is due to be constructed as part of the SRS Superfund remediation, though it looks like not much has been done yet besides brush-cutting. The small bridge immediately north of Curtiss Street has also been re-decked for trail use. Lazy Lane-West Queen Street is in the early stages of planning as a state project and will bring the trail almost to the end of the active railroad.

Heading north from Plainville, the trail construction from Northwest Drive to Red Oak Hill Road in Farmington is moving right along, with most of the trail already paved. The last major piece here will be the Route 6 bridge, which is due to be installed in 2017.

The active railroad between Birch Street in Southington and Northwest Drive in Plainville will present challenges to resolving the remaining gap, but a study is underway to determine the best possible routing.

Air Line State Park Trail

Construction Update - South

December, 2016 by martinip

Was in East Hampton briefly yesterday - it looks as though work is now underway to extend the trail west from the center of East Hampton to Alden's Crossing. Grading had been done and there were new railings on the footbridge east of Alden's Crossing. The next segment will be from Alden's Crossing to the Portland town line, with Portland also beginning work to build out its portion of the trail.

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