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

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.

Accordion

Air Line State Park Trail

Air Line Trail going north.

December, 2016 by trainman1957

Wonderful news, the bridge is in going north in Thompson,Ct it is in finally. Now you can walk only over the bridge. Soon in the spring you will be able to ride from Putnam to the Mass line.

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

Closed for Eagle Nesting

December, 2016 by lindseylouise24

The trail is closed from November to April for Eagle nesting! Happy for the birds. Made me bike somewhere else and find some delicious roadside turnips.

Larkin State Park Trail

Disappointed

November, 2016 by susanrider

I drove about 50 minutes to the trailhead in Naugatuck and from the parking lot, the trail rose about 40 degrees and was rough and covered with leaves. Perhaps it smooths / levels out a bit later, but it looked as it it were suitable for a mountain bike only. I drove to another trail.

Air Line State Park Trail

Airline Trail - North

October, 2016 by CW4

I started at South Brook ST just west of Route 6. The surface of the trail was improved but with rough rocky gravel (1") on the surface. There was 3 1/2 miles of that, then it changed to a hard packed surface that was fun and easy to ride. I went the remaining 7 miles to Promfret Station, at the Route 169 crossing. From there it was back to the start, just over 11 miles. It was a very pretty ride except for the rough gravel at the start and end of my trip.

The remaining trail to Windham is in fine shape as I have done it on another trip. It is about 6 miles to the Route 6 crossing and another 2.5 to the Frog Bridge in Willimantic.

I hear that a sewer line is to be installed within the last 3 miles of the trail right-of-way in 2017 or 2018. That will complete the trail to the Quinnibaug River in Putnam.

Farmington Canal Heritage Trail

Farmington Canal Trail - New Improvments

October, 2016 by CW4

I recently road the newly constructed Cheshire Section, West Main Street to Route 322 in Southington. It is in place and ready to use. It will be officially opened in December but don't let that stop you. I thought it was very pretty. If you roll on north to the trails current end in Southington near Curtiss Street, it is 8 miles one way.

When you get back to West Main Street, if you have more energy, turn left on West Main and right on Walnut. Go 3/4 miles to Cornwall where you can continue south toward New Haven. Rumor has it that the missing 3/4 section is designed and will be started in 2017.

A new section of the Farmington Canal Trail is under construction from Northwest Drive in Plainville to the current southerly terminus in Farmington. A 2017 finished is possible for this new piece of trail. All that will leave out is the short Southington and Plainville sections.

Pequonnock River Trail

nice trail

October, 2016 by kmanto

My husband and I tried this for the first time. Really nice quiet trail. Just be careful as there are steep drop offs on one side. Lovely and will return!!

Farmington Canal Heritage Trail

New section in Cheshire

October, 2016 by pausau

A new 1.5 mile section opened in Cheshire in September 2016. It is not connected to the northern terminus of the old section at Cornwall Ave., but is easily reached from that point by taking a one-mile detour on lightly-used Willow Street. Within this section from W. Main St. (Rt. 68) to Jarvis St. there are the abutments of two bridges that once carried other tracks over this railroad and canal. At each site there is a large sign which was blank when I was there but should soon describe what was there. There is also a well-built observation platform overlooking a stagnant pond. This may have been a wide spot in the canal where barges going in oposite directions could pass.
Just north of Jarvis St. there is a large parking lot with two composting toilets. The trail north of here seems to be almost completed all the way to connect with the existing section in Southington, but there was a sign indicating closed, under construction when I was there. A very interesting little section.

Southwick Rail Trail

Where are the water fountains?

October, 2016 by lreopel

Other than there not being any way to refill my water bottle or get water without taking my own, the trail is a calming and beautiful place that is great for any age.
I have noticed that there are a handful of water fountains that are not usable (no running water)! Please, if you are wondering why there are not any working water fountains or if you want to get some put up at the "rest stops" let me know!

Farmington Canal Heritage Trail

A lovely place for a ride!

September, 2016 by arctander2

Kudos for all who have put in the energy and effort to make this trail happen! I just took 3 hours (up and back) from Plainville to Cheshire! Really lovely!

And it looks like they're almost completed on paving the bridges! Perhaps the next time I visit it'll be completed.

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