Southwick, MA Trails and Maps

1061 Reviews

Looking for the best trails around Southwick?

Explore the best rated trails in Southwick, MA. Whether you're looking for an easy walking trail or a bike trail like the Windsor River Trail and Mattabassett Trolley Trail . With more than 50 trails covering 418 miles you’re bound to find a perfect trail for you. Click on any trail below to find trail descriptions, trail maps, photos, and reviews.

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Activities
Length
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Type
50 Results
Activities
Length
Surfaces
Type

Air Line State Park Trail

54.6 mi
State: CT
Ballast, Crushed Stone, Dirt, Gravel

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Billings Trail

3.3 mi
State: CT
Dirt

Bloomfield Greenway Multi-Use Trail

1.8 mi
State: CT
Asphalt

Bridge of Flowers

0.1 mi
State: MA
Concrete

CTfastrak Multi-Use Trail

4.4 mi
State: CT
Asphalt, Concrete

Canalside Rail Trail

3.6 mi
State: MA
Asphalt

Captain John Bissell Trail

4.5 mi
State: CT
Asphalt

Charter Oak Greenway

16.6 mi
State: CT
Asphalt

Cheney Rail Trail

1.7 mi
State: CT
Crushed Stone

Chicopee River Canal Rail Trail

0.21 mi
State: MA
Asphalt

Columbia Greenway Rail Trail

2.4 mi
State: MA
Asphalt

Connecticut Riverwalk and Bikeway

5.4 mi
State: MA
Asphalt

Corkscrew Rail Trail

3.8 mi
State: NY
Dirt

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Grand Trunk Trail

6.2 mi
State: MA
Crushed Stone, Dirt, Gravel

Hanover Pond Trail

1 mi
State: CT
Asphalt

Harlem Valley Rail Trail

23.2 mi
State: NY
Asphalt, Crushed Stone
Accordion

Hartford Riverwalk

1.7 mi
State: CT
Asphalt

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt

Larkin State Park Trail

10.8 mi
State: CT
Cinder, Crushed Stone, Dirt, Gravel

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

48.4 mi
State: MA
Asphalt, Cinder, Crushed Stone, Dirt, Gravel

Mattabassett Trolley Trail

2.9 mi
State: CT
Asphalt

Middlebury Greenway

4.5 mi
State: CT
Asphalt

Middletown Westlake Area Bikeway

2.2 mi
State: CT
Asphalt

Naugatuck River Greenway

5.4 mi
State: CT
Asphalt

New Milford River Trail

5 mi
State: CT
Asphalt, Crushed Stone, Dirt

Putnam River Trail

2 mi
State: CT
Asphalt

Quinebaug River Trail

4.8 mi
State: CT
Asphalt

Quinebaug Valley Rail Trail

5.7 mi
State: MA
Ballast, Cinder, Dirt, Grass

Quinnipiac Linear Trail

1.25 mi
State: CT
Asphalt, Gravel

Quinnipiac River Gorge Trail

1.3 mi
State: CT
Asphalt

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

Rocky Hill Trail

0.9 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
Crushed Stone

Southern New England Trunkline Trail

22 mi
State: MA
Asphalt, Ballast, Crushed Stone

Southwick Rail Trail

6.5 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

Ware River Rail-Trail

12 mi
State: MA
Ballast, Dirt, Grass, Gravel

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone

Windsor River Trail

0.8 mi
State: CT
Asphalt
Trail Image Trail Name States Length Surface Rating
The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...
CT 54.6 mi Ballast, Crushed Stone, Dirt, Gravel
Visitors to the Ashuwillticook Rail Trail will find the full splendor of the scenic Berkshires along this nearly 12-mile-long paved trail. The Ashuwillticook (ash-oo-will-ti-cook) follows MA 8 through...
MA 11.9 mi Asphalt
Open in several disconnected segments, the Billings Trail is a dirt path that traverses a lovely scenic and wooded landscape outside Norfolk in northern Connecticut. Built on the abandoned railbed of...
CT 3.3 mi Dirt
Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...
CT 1.8 mi Asphalt
The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...
MA 0.1 mi Concrete
A part of Connecticut's first bus rapid transit line, the CTfastrak Trail serves as recreational and multi-use path for walking and bicycling between Downtown New Britain and Newington Junction. The...
CT 4.4 mi Asphalt, Concrete
The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...
MA 3.6 mi Asphalt
The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...
CT 4.5 mi Asphalt
The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...
VT 18.1 mi Dirt
The Charter Oak Greenway offers more than 16 miles of paved pathway through Hartford and its eastern suburbs. At first glance, the trail looks as if it is simply a highway side path, but the journey...
CT 16.6 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 1.7 mi Crushed Stone
The Chicopee Center Canal Walk offers a short pleasant route in Chicopee, a small city on the outskirts of Springfield in southern Massachusetts. The pathway closely follows the slow-moving canal and...
MA 0.21 mi Asphalt
The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...
MA 2.4 mi Asphalt
The Connecticut River Walk and Bikeway, which will one day run 21 miles along the river, currently has two open segments. The longest stretches 3.7 miles from the Chicopee town line to the South End...
MA 5.4 mi Asphalt
The first section of the Corkscrew Rail Trail opened in June 2015. It begins at Knapp Road in Stephentown and heads south under a shady tree canopy towards New Lebanon, near the New York/Massachusetts...
NY 3.8 mi Dirt
First a canal, then a railroad, and now a trail define the history of the Farmington Canal Heritage Trail. Completed segments span Connecticut south to north, from New Haven to the Massachusetts...
CT 48.3 mi Asphalt
A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...
CT 16.5 mi Asphalt, Crushed Stone
The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...
MA 6.2 mi Crushed Stone, Dirt, Gravel
The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...
CT 1 mi Asphalt
Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...
NY 23.2 mi Asphalt, Crushed Stone
Accordion
The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...
CT 1.7 mi Asphalt
It’s hard to pick a favorite season to experience the Hop River State Park Trail, set amid the dense forests of Eastern Connecticut. Sections of the 20-mile rail-trail dive through steep rock cuts...
CT 20 mi Crushed Stone
The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...
CT 3.1 mi Dirt
The Larkin State Park Trail meanders 10.8 miles through the woods and around the lakes and low hills of southwestern Connecticut. The rail-trail follows the route of the New York & New England...
CT 10.8 mi Cinder, Crushed Stone, Dirt, Gravel
The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...
MA 9.6 mi Asphalt
The Massachusetts Central Railroad was destroyed by a hurricane in 1938, but the 104-mile corridor is being reborn as a cross-state rail-trail. Currently, nearly 50 miles from Boston to Northampton...
MA 48.4 mi Asphalt, Cinder, Crushed Stone, Dirt, Gravel
Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...
CT 2.9 mi Asphalt
The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...
CT 4.5 mi Asphalt
Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...
CT 2.2 mi Asphalt
The Naugatuck River Greenway will one day span 44 miles from Torrington to Derby in western Connecticut, but is currently open in a few short disconnected segments totaling just over 5 miles. The...
CT 5.4 mi Asphalt
The first phase of the New Milford River Trail runs southeast from Gaylordsville via the scenic but lightly traveled River Road, through Sega Meadows to Boardman Bridge, a distance of about 5 miles....
CT 5 mi Asphalt, Crushed Stone, Dirt
The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...
CT 2 mi Asphalt
The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...
CT 4.8 mi Asphalt
The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...
MA 5.7 mi Ballast, Cinder, Dirt, Grass
The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...
CT 1.25 mi Asphalt, Gravel
The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...
CT 1.3 mi Asphalt
The Railroad Ramble occupies a corridor abandoned by the Central New England Railroad, which provided service from 1871 through 1967. In Lakeville, the trail can be found just off of Route 41 behind...
CT 1.7 mi Asphalt, Dirt, Grass
The Redstone Rail Trail is built on the former New York, New Haven & Hartford Armory Branch, which in turn is a former branch line of the New York & New England RR. Its name comes from the numerous...
MA 1.4 mi Asphalt
The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...
MA 0.9 mi Asphalt
The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...
MA 1.62 mi Crushed Stone
The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...
MA 22 mi Asphalt, Ballast, Crushed Stone
The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...
MA 6.5 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
Coming in at just under 3 miles, the Sue Grossman Still River Greenway is anchored by the towns of Winchester to the north and Torrington to the south. It occupies the right-of-way of the Naugatuck...
CT 2.9 mi Asphalt
The Trolley Trail runs through Plainfield and is a key link the East Coast Greenway. Plans are to use this trail as a link between the Moosup Valley State Park Trail and the Airline State Park...
CT 0.75 mi Asphalt
The Rockville Spur, a section of Vernon Rails-to-Trails, is a stone-dust rail-trail stretching 4.2 miles into the heart of historical Rockville. The trail begins on Warren Avenue in Vernon, but you’ll...
CT 4.2 mi Crushed Stone, Dirt
This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...
MA 12 mi Ballast, Dirt, Grass, Gravel
The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...
MA 0.7 mi Crushed Stone
Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...
CT 5.4 mi Asphalt
The Windsor River Trail is a paved trail along the Connecticut River in Windsor Meadows State Park. The trail begins at the state park’s parking lot on E Barber St. The Captain John Bissell Trail,...
CT 0.8 mi Asphalt

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Trails by activity

Columbia Greenway Rail Trail

MA - 2.4 miles

The Columbia Greenway Rail Trail offers just over 2 miles of paved, tree-lined pathway through Westfield in southwestern Massachusetts. The trail runs from Main Street, across the Great River Bridge...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

Mattabassett Trolley Trail

CT - 2.9 miles

Where a trolley once ran, now you can too on the south bank of the Mattabessett River. The electrified trolley shuttled passengers from Berlin to Middletown and beyond. The smooth blacktop and an easy...

South Spencer Rail Trail

MA - 1.62 miles

The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...

Accordion

Middlebury Greenway

CT - 4.5 miles

The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...

Middletown Westlake Area Bikeway

CT - 2.2 miles

Over 2 miles from start to finish, this U-shaped trail meets both the commuting and the recreational needs of local residents in Middletown. The trail begins on Middle St, marked by a trailhead with a...

Naugatuck River Greenway

CT - 5.4 miles

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

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

Windsor Locks Canal State Park Trail

CT - 5.4 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...

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....

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...

Quinnipiac River Gorge Trail

CT - 1.3 miles

The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...

Kress Family Trail

CT - 3.1 miles

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

Putnam River Trail

CT - 2 miles

The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...

Southwick Rail Trail

MA - 6.5 miles

The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...

Quinnipiac Linear Trail

CT - 1.25 miles

The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...

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...

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...

Trolley Trail (CT)

CT - 0.75 miles

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

Hartford Riverwalk

CT - 1.7 miles

The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...

Windsor Locks Canal State Park Trail

CT - 5.4 miles

Note: Per the State of Connecticut's website, the trail is open from dawn to dusk April 1–November 14. Eagle nesting activities can delay the opening of the southern trail head in Windsor...

Quinebaug River Trail

CT - 4.8 miles

The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...

Cheney Rail Trail

CT - 1.7 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...

Hartford Riverwalk

CT - 1.7 miles

The Hartford Riverwalk is a charming network of paved pathways for cyclists and pedestrians that runs along the banks of the Connecticut River through the state capital. The trail provides an off-road...

Accordion

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

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...

Bloomfield Greenway Multi-Use Trail

CT - 1.8 miles

Bloomfield Greenway Multi-Use Trail is 1.8 miles between Bloomfield and Simsbury. The trail is envisioned to someday act as a connector between the City of Hartford and the Farmington Canal Heritage...

Canalside Rail Trail

MA - 3.6 miles

The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...

Bridge of Flowers

MA - 0.1 miles

The Bridge of Flowers delights the senses of visitors walking among the trees and blossoms on the old trolley bridge spanning the Deerfield River, which connects two communities in northwestern...

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...

Grand Trunk Trail

MA - 6.2 miles

The overall goal of the Grand Trunk Trail in south-central Massachusetts is to connect the communities of Brimfield, Sturbridge, and Southbridge by trail. Currently, two sections of the trail are...

Naugatuck River Greenway

CT - 5.4 miles

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

Hanover Pond Trail

CT - 1 miles

The Hanover Pond Trail is a mile-long rail-trail in Meriden, Connecticut offering scenic natural escape combined with historical exploration. The smooth asphalt trail is open to a diverse range of...

Putnam River Trail

CT - 2 miles

The Putnam River Trail extends between Arch Street in the Putnam District and Providence Street to the south. The trail follows the east bank of the Quinebaug River between the river and Kennedy...

Manhan Rail Trail

MA - 9.6 miles

The Manhan Rail Trail, well integrated into the local communities it serves, offers a pleasant ride or stroll. It conveniently weaves together parks, community points of interest, neighborhoods, and...

Quinnipiac River Gorge Trail

CT - 1.3 miles

The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...

Ware River Rail-Trail

MA - 12 miles

This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...

Quinebaug Valley Rail Trail

MA - 5.7 miles

The Quinebaug Valley Rail Trail runs on the corridor once occupied by the Southbridge & Blackstone line of the Providence & Worcester Railroad, transforming a corridor once designed to link rural...

Trolley Trail (CT)

CT - 0.75 miles

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

Rocky Hill Trail

MA - 0.9 miles

The Rocky Hill Trail weaves through the tranquil greenery of the Burts Bog Greenway Conservation Area in Northampton, Hampshire County. The 121-acre peat bog is an ecologically sensitive site that's...

Southern New England Trunkline Trail

MA - 22 miles

The Southern New England Trunk Line Trail (aka the "SNETT") was designated as a National Recreation Trail in 1994. It is built upon a segment of the former right-of-way of the New Haven Railroad's...

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...

Farmington River Trail

CT - 16.5 miles

A dozen miles west of Connecticut’s capital of Hartford, the Farmington River Trail forms a 16.5-mile arc that connects to the larger Farmington Canal Heritage Trail on both ends. The rail-trail was...

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....

Accordion

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...

Quinnipiac Linear Trail

CT - 1.25 miles

The Qunnipiac Linear Trail is an easy multipurpose path in Wallingford, Connecticut. The trail skirts Community Lake while traveling a heavily wooded corridor along the Quinnipiac River. It is one of...

Middlebury Greenway

CT - 4.5 miles

The Middlebury Greenway provides a paved, off-road option for a self-propelled journey across suburban Middlebury. The trail touches on several business districts and parks, ending at an amusement...

Kress Family Trail

CT - 3.1 miles

The 3.1-mile Kress Family Trail in Roxbury occupies the former route of the Shepaug Valley Railroad (the Shepaug, Litchfield and Northern Railroad). The railroad was famously known as the “crookedest...

South Spencer Rail Trail

MA - 1.62 miles

The South Spencer Rail Trail runs for less than 2 miles from downtown Spencer to an area south of town near Spencer State Forest. The path, which is also known as the Depot Trail, occupies a former...

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...

Quinebaug River Trail

CT - 4.8 miles

The Quinebaug River Trail exists in two segments in northwest Connecticut. The northern section parallels Park Road and Tracy Road for about 2 miles in an industrial section of Putnam with few trail...

Canalside Rail Trail

MA - 3.6 miles

The well-maintained Canalside Rail Trail provides users with a variety of trestle bridges, views of waterbirds stalking fish and frogs, and gentle grades that alternate between open sky and forested...

Ware River Rail-Trail

MA - 12 miles

This unpaved state-owned trail is open for public use from Coldbrook to Baldwinville. An on-road detour is necessary through the village of Baldwinville, but the right-of-way is open for public use on...

Harlem Valley Rail Trail

NY - 23.2 miles

Paralleling the Connecticut and Massachusetts borders, which lie only a few miles away, the Harlem Valley Rail Trail is a beautiful paved wooded pathway along the former New York & Harlem Railroad...

Westville Lake Community Trail

MA - 0.7 miles

The Westville Lake Community Trail offers a short, scenic excursion along the east bank of Westville Lake in Southbridge. Much of the crushed-stone pathway is under a lush tree canopy. Along the way,...

Captain John Bissell Trail

CT - 4.5 miles

The Bissell name looms large in this part of New England, and has been immortalized in multiple ways, including the Bissell Ferry, the Bissell Memorial Bridge and now, the Captain John Bissell trail,...

Air Line State Park Trail

CT - 54.6 miles

The Air Line State Park Trail winds nearly 55 miles from the northeast corner of Connecticut, where the state borders Massachusetts, down to East Hampton in the heart of the state. The pathway is...

Quinnipiac River Gorge Trail

CT - 1.3 miles

The Quinnipiac River Gorge Trail is a 1.3-mile rail-trail in Meridan, Connecticut. The trail occupies the former railbed of the Meriden, Waterbury & Connecticut River Railroad, a 17-mile line which...

Southwick Rail Trail

MA - 6.5 miles

The Southwick Rail Trail extends from the Massachusetts–Connecticut state line north to the Westfield town line and connects to the Columbia Greenway Rail Trail. Along the way, it travels through...

Catamount Trail - Sections 1 and 2

VT - 18.1 miles

The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to North Troy near Canada. The trails are popular for winter...

Recent Trail Reviews

Windsor Locks Canal State Park Trail

A beautiful trail in need of resurfacing

May, 2022 by eajack

My wife and I rode our recumbent trikes on the entirety of this trail on a Saturday evening. For the most part, we encountered only walkers. And based on the surface condition of the trail, I understand why. The pavement has deteriorated and is full of root-bumps and small dips. It was a very rough ride.

I would recommend this trail for walkers, joggers, or cyclists if you've got a bike/trike with a suspension. The bulk of the trail is on the old towpath between the river and the canal, so other than the north and south ends, you are separated by water from the rest of the world. This makes for a quiet, relaxing, and scenic trek. The northern terminus near the parking lot, which also forms a "T" with the CT 190 bridge, and the southern terminus by the renovated mill building are new and in great shape. All we need now is for Connecticut to resurface the original portion... even stone dust would be better than the broken pavement.

Ashuwillticook Rail Trail

Ashuwillticook Rail Trail

May, 2022 by bktourer1

If you haven't seen or been there yet, new 1.5 section towards Pittsfield was officially opened last week. Ends/Starts at Crane Road. Parking lot and toilets are available. New dirt lot on Rt. 8 before you turn off US7/Rt 8 connector road

Hartford Riverwalk

Lovely!

May, 2022 by afalls4

I went here on a beautiful Sunday afternoon. What a lovely place! This is a paved trail that follows the river and has a nice playground and picnic area at one end. There are various sculptures related to Abraham Lincoln along the way. It was very relaxing to stroll along the water. The views of the bridges and the Hartford skyline are stunning. Will definitely return!

Accordion

Harlem Valley Rail Trail

What can I say, this is a great trail for a bike ride. Great scenery, flat for the most part and wasn't a lot of people. Must do trail

May, 2022 by carlosccalhoun

What can I say, this is a great trail for a bike ride. Great scenery, flat for the most part and wasn't a lot of people. Must do trail

Middlebury Greenway

Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.

May, 2022 by carlosccalhoun

Trail is nice for the size, well paved but hills. You can park on the back side of Maggie's and there are other places to park along the way.

Air Line State Park Trail

South from Willimantic 5*; north from Windham Rt 6 (went 2 miles) to Putnam 3*

April, 2022 by andrix

On e Bikes; trail to north from Windham generally passable but long wet areas (eventually turned around) and trail a bit rougher than going south from Willimantic. The south trail is in much better shape and had inviting scenery with streams, farms and wetlands/lakes + virtually no wet areas on trail. Went to RT 87 (about 8 miles) from Willimantic. Plan to do this again and go further.

Farmington Canal Heritage Trail

Farmington to Canton

April, 2022 by aldcon_tl

Great trail and very scenic. All paved and pavement in very good shape. Parked at lot on New Britain Ave. and went NW to Collinsville and then to Rte. 44 in Canton. Then rode trail back to start.
10 miles each way. Very enjoyable journey. 90%+ of ride is on nice wide trail. First half of trip is constant, gentle up gradient. Ride back about 60% faster since going mostly gently downhill along river.

Air Line State Park Trail

Pomfret section of trail

April, 2022 by aldcon_tl

Parked at lot on Railroad St off of 44. New parking lot and pavilion with new overpass for trail over main road. Took trail NE to Town Farm Rd. and then streets into Putnam. Trail in this section gets average rating of 2+. Trail base is coarse rock (1.5" +) with washed out ruts. Somewhat bumpy ride. Only good for bikes with wider tires. In Putnam went south on Putnam River Trail (excellent paved trail) south to bridge over Quinebaug River. Crossed river climbed up steep hill to get to old rail trail and took this back to starting point.
Next went SW from rail station on trail to Covell Road. This section of trail in very good shape. Hard packed gravel base. I'd rate this a 4. Easy going for most bikes.

Farmington River Trail

Best Trail in Ct.

April, 2022 by whitney495

I usually park at the lot at the corner of Red Oak Hill dr. and New Britian ave. and head north. You go thru Unionville then to Collinsville where you can stop for a drink and bite to eat. You can go back to your car from there (16 miles round trip) or continue on to Canton and even farther. Well, maintained, great scenic views of the Farmington River rapids. It can get crowded on weekends. During the week, is perfect.

Air Line State Park Trail

It could be better

March, 2022 by revgil

I live close to the Pomfret Station so I decided to give the Airline Trail North another chance. I had ridden from the new bridge north toward Putnam last fall and found that much of it to be unride-able. Today I headed south, and after a short time, I realized it was just too rough for my seventy year old body. Horse’s hooves and dirt bikes had dug it up.
It’s really a shame that the powers that be don’t pony up and pave it. I think that it could be one of the best trails in the country.

Hanover Pond Trail

Short and Sweet

February, 2022 by petesalomone

Pleasant trail between Platt HS and Quuinnipiac gorge. A good walk in the woods and along the short of Hanover Pond. Be sure to read the signage about the former amusement park.

Connecticut Riverwalk and Bikeway

Awesome run, it was late 40th and windy however i was so happy to run outside. I like the river view and and it's away from the traffic. I can get a decent 6 miles out it. Good place to stretch by the stairs amazing view.

February, 2022 by yikertam

Awesome run, it was late 40th and windy however i was so happy to run outside. I like the river view and and it's away from the traffic. I can get a decent 6 miles out it. Good place to stretch by the stairs amazing view.

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