Southwick, MA Bike Trails and Maps

854 Reviews

Looking for the best Bike trails around Southwick?

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

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Activities
Length
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Type
33 Results
Activities
Length
Surfaces
Type

Ashuwillticook Rail Trail

11.9 mi
State: MA
Asphalt

Billings Trail

3.3 mi
State: CT
Dirt

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

Farmington Canal Heritage Trail

48.3 mi
State: CT
Asphalt

Farmington River Trail

16.5 mi
State: CT
Asphalt, Crushed Stone

Harlem Valley Rail Trail

17.2 mi
State: NY
Asphalt, Crushed Stone

Hop River State Park Trail

20 mi
State: CT
Crushed Stone

Kress Family Trail

3.1 mi
State: CT
Dirt

Manhan Rail Trail

9.6 mi
State: MA
Asphalt

Mass Central Rail Trail

38 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
Accordion

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

Railroad Ramble

1.7 mi
State: CT
Asphalt, Dirt, Grass

Redstone Rail Trail

1.4 mi
State: MA
Asphalt

South Spencer Rail Trail

1.62 mi
State: MA
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

Westville Lake Community Trail

0.7 mi
State: MA
Crushed Stone
Trail Image Trail Name States Length Surface Rating
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
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 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
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
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 17.2 mi Asphalt, Crushed Stone
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 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 40 miles from Boston to Northampton...
MA 38 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
Accordion
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 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 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 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 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 Locks. Due...
CT 5.4 mi Asphalt

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Trails by activity

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...

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...

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,...

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...

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...

Sue Grossman Still River Greenway

CT - 2.9 miles

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...

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...

Stratton Brook State Park Trail

CT - 1.2 miles

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

New Milford River Trail

CT - 5 miles

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

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...

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,...

Mass Central Rail Trail

MA - 38 miles

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 40 miles from Boston to Northampton...

Hop River State Park Trail

CT - 20 miles

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...

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...

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...

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...

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...

Ashuwillticook Rail Trail

MA - 11.9 miles

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...

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...

Farmington Canal Heritage Trail

CT - 48.3 miles

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...

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 Locks. Due...

Naugatuck River Greenway

CT - 5.4 miles

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

Southwick Rail Trail

MA - 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...

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...

Accordion

Farmington Canal Heritage Trail

CT - 48.3 miles

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...

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...

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...

Hop River State Park Trail

CT - 20 miles

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...

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...

Billings Trail

CT - 3.3 miles

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

Columbia Greenway Rail Trail

MA - 2.4 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...

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...

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...

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...

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...

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...

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...

Charter Oak Greenway

CT - 16.6 miles

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...

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,...

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...

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...

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...

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...

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...

Harlem Valley Rail Trail

NY - 17.2 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...

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...

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 Locks. Due...

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...

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...

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....

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...

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...

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...

Mass Central Rail Trail

MA - 38 miles

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 40 miles from Boston to Northampton...

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...

Charter Oak Greenway

CT - 16.6 miles

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...

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...

Sue Grossman Still River Greenway

CT - 2.9 miles

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...

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...

Recent Trail Reviews

Ashuwillticook Rail Trail

Super Trail

June, 2019 by tbobinsky_tl

Beautiful scenery, good asphalt surface with big bumps well marked. Not much at the south end but great food and ale at the north end...plan accordingly. May also want to plan camping at Clarksburg State Park...about 15 minutes from the trail head. Met a few RTC members. So far for me, this is the best trail in Massachusetts. Please support - and a big thank you to - the Conservation Trust! Signed, one happy biker from New Hampshire.

Ashuwillticook Rail Trail

Great Trail

June, 2019 by coachmrpaul

Found this gem while visiting the Berkshire’s. Well maintained and a pleasure to ride. I went from Adams to Lanesborough. I appreciate the markings for the rises in the pavement (very few) due to roots coming up. Bravo Berkshire area for taking care of this one.

Captain John Bissell Trail

Great hard surface trail, light-traffic roads

June, 2019 by kathleenpwood

We love all of Main St, South Windsor, and it's perfect for a bike ride. I recommend starting at the top of Main St rather than by Chapel Rd as suggested here. It's a sample of old New England with lots of well-maintained vintage homes (including the birthplace of Jonathan Edwards), tobacco barns, fields, & farms. The road itself is a very moderate incline, similar to rails-to-trails. The bike trail alongside I291 is also very easy biking. We only had time to go about halfway on that portion before we needed to head back. An absolutely perfect ride!

Accordion

Ashuwillticook Rail Trail

Well Maintained and Peaceful Ride

June, 2019 by tnjgronberg

Great scenery along the entire route. We started at the south end and rode all the way to the north end and back.

Farmington River Trail

Excellent

June, 2019 by yiwang100

This is the 1st trail I rode since started biking 7 years ago. It is still one of my favorites. Close to the north end there is a small town with nice restaurants and a surprisingly good small museum displaying local history. It is well worth a visit.

Farmington Canal Heritage Trail

Very Nicely Paved Trail

May, 2019 by stvatandem

My wife and I rode our tandem from the Brickyard Rd Trailhead northward to the Phelps Rd Trailhead (just short of the MA line). The route is pretty well marked and the pavement is good. Most of the trail/roadway crossings have pedestrian/cyclist buttons to trigger the traffic warning signals and the cars do stop when they see you standing at the crosswalk.
Regarding places to eat: We only saw a sign for one business along the trail. I recommend doing a google search ahead of time to see what's nearby and plan accordingly.

Ashuwillticook Rail Trail

Nice Ride Overall

May, 2019 by airalapb

I rode the 24 mile loop it's pretty much a gradual descent from South to North overall it's in great condition lots of benches and some picnic like tables along route. There are however locations where either roots have damaged the pavement or buckling has occurred they are spray painted and there is signage indicating they are coming up they are pretty high 3-4 inches so keep an eye out for them. These locations are within 4 miles of South parking lot by the mall. I will ride again for sure.

Harlem Valley Rail Trail

Biking Rails to Trails in Massachusetts from Missouri

May, 2019 by riepejar

We were told once we arrived on the trail, that it was not complete. We discovered that we had to share a gravel road that was not on the rail portion. The trail to the North was in process of being worked on and not at all passable. Some notice needs to be posted saying Trail is under construction or sharing roads with cars is noted. The Map looks Identical to the Cape Cod trail which was excellent .....no indication that the Harlem trail was not complete

Hop River State Park Trail

Hop River Trail Construction News

February, 2019 by CW4

Contact with the Hop River design team has developed some news on the last remaining undeveloped area on the Hop River Trail. The section on the Windham side of the Willimantic River is under construction. A late summer opening is anticipated. This work will allow traffic over the Willimantic River from the current end at Mackey's Ag. store. A parking area is also part of the work.

The Trail from the Columbia town line to Kings Road (the current end of the developed trial) will be under design late this year. Bids, construction and all that stuff pushes the completion into 2021.

So late this summer, with a MT bike, you will be able to cross the river from Windham and follow the unimproved rail bed to Flanders Road, turn right to Kings Road and get back on the improved trail, That's less than a mile of off trail and local road.

Redstone Rail Trail

nice easy trail

October, 2018 by slevesque_tl

My kids and I love to take our dogs for a walk here

Ashuwillticook Rail Trail

Scenic fun

October, 2018 by raines100

The trail is in good condition, flat, clean, and scenic. It checked all the boxes.

Air Line State Park Trail

Response to Construction News

September, 2018 by blueskye

In April 2018 the Windham Town Council approved $1,300,000 for rehabilitation on the Willimantic River bridge behind Mackeys. This would include 800 feet of trail. It was put out for bids due on July 26th. I haven't seen any work yet. There is still the bridge over the Hop River which looks to be in terrible shape and may never be repaired.

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