Explore the best rated trails in Longmeadow, 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 440 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.
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,...
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...
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 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...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
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,...
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...
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...
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
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...
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...
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...
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...
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,...
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...
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...
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...
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...
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...
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...
Burrillville Bike Path runs for just over a mile through its namesake rural community in northwest Rhode Island. It connects the villages of Pascoag and Harrisville through a corridor that once...
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...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
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...
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...
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...
The North Central Pathway is envisioned as a trail network connecting points of interest through and between Winchendon and Gardner. Several completed sections of trail make for a lovely ride or walk...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
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...
Throughout history, the Blackstone River has been an important waterway, from its use by American Indians who fished its once-abundant salmon to its role as a major artery for the transportation of...
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...
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...
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...
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 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...
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...
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,...
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 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...
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...
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...
This 5.8-mile trail is part of the planned East Coast Greenway, an off-road path that will eventually run from Calais, Maine, to Key West, Florida. The Moosup Valley State Park Trail will connect with...
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...
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...
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...
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...
Built in the 1910s by the Boston and Maine Railroad (B&M) as part of the Connecticut River Division Main Line, the route introduced daily service to the B&M Fort Hill Branch in the early 1920s to meet...
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...
The Ashuelot Recreational Rail Trail passes such scenic and historical landmarks as covered bridges, abandoned mills, and postcard-perfect towns. Starting on asphalt in Keene, the rail-trail can be...
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...
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...
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...
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...
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...
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...
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...
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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...
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...
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...
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...
I've ridden all sections in Southbridge, Sturbridge and Brimfield. The last is most extensive as it allows several different routes in the same area. The surface runs from gravel to loose crushed stone to grass and mud depending on the area as well. Inexperienced or older riders may find some parts of the Brimfield trails difficult. But if one takes their time there are some marvelous water views of the Quinebog River and adjoining marshes on that end of the trail to enjoy. The Southbridge/Sturbridge end of the trail allows a 4 mile plus run from Westville Dam out to the Calcutt Bridge and back. Adding in the Westville Community Trail in the Westville Reservation (a narrow and winding one that runs the woods on the east side of the river) adds another .75 miles to the route approximately.
Nice family friendly trail close by. Great for children to ride their bikes and walk your pets.
On Feb. 17, 2020, I walked from Smith Street, East Hampton west for 2.9 miles through the tunnel under Rt. 66 where the improved section ends. This section has a good surface of stone dust. There is only 0.25 mile gap between the final 0.7 mile section in East Hampton where that newer segment connects to the 2.3 mile long trail in Portland. There are plans to build a boardwalk through this section to make the connection, as the trail is a running stream with several inches of water.
The trail has a slight break at Main Street that is a bit confusing to navigate. When heading west, turn right on Main Street, cross Main Street at the light, and walk through the parking lot in front of the fire department building to pick up the trail.
At the eastern end of the trail, the bridge over the Willimantic River in Willimantic on the Hop River State Rail Trail received a new deck in 2019 and opened to the public in September 2019, thus making a direct connection to the Air Line Trail.
I have ridden this a few times. Very nice trail. Well maintained. Beautiful area.
The trails in Vernon are among the most maintained of all trails in Central and Easter CT. There's plenty of parking along the trails which gives you easy access. The scenery is amazing including bridges, side paths, and tunnels.
It's too bad that so many of these trails don't allow the use of snowmobiles and off-road motorcycles. I see a lot of people complain about motored vehicles, but it really makes no sense to me. To me, both activities are equal and should have equal access. You have one group of people who enjoy hiking and biking, and another group of people who enjoy dirt-biking and snow-mobiling. Why does the hiking biking community always win out? Why do they get priority over the other group? Are the activities we enjoy less valuable/important than the activities you enjoy? I'm not whining, but I don't think it's fair. There is no logical reason to allow one activity and restrict the other. It's done out complete bias against and inconsideration for the preferred activities of other groups of people. If noise, speed etc. is the issue, then set rules regulating these things, don't ban the activity altogether.These trails should be open to all applicable activities, with a set of rules allowing everyone to enjoy the trails with each other.
I went on this trail as a runner. The first half mile is nicely paved and was very nice. After that though the trail was not very runner friendly. Lots of water hazards, loose rocks, up down ruts and off road vehicle traffic. The trail itself is beautiful with very few road crossings. I could see having a good time as a mountain biker but not great for running.
I did the loop today going north on this River Trail then back south on the FCT. The gravel is at mile 12.3 after a little on the road segment but it only lasts about 3/4 mile. I had to go very slowly on the gravel dust because I was on my road bike (22mm) but it was tolerable because it was short (&pretty). At the entrance to the Stratton State Park a sign indicates you can take the road downhill to Simsbury felt safe. froDOWNdown to Simsbury which was much better on thin tires. indicating on esign The on the road section was well marked today - although many of the signs were large temporary ones. I how
This trail starts out OK, but as you move further North, into to country the trail narrows and is less maintained. My biggest concern is there is not enough parking places, entrances , and no benches.
This is an amazing trail" with windy. curves, up and down climbing, plenty of benches, and lots of awesome bridges.
Beautiful and no crowded from Amenia to Milerton - 8 plus miles from the parking lot indicated on the map. Trail ends in Millerton - I did not ride along rite 22 to pick up the rail trail again for the final five r so miles, as it is crazy town to ride on Route 22. Overall, a pleasant there and back (I went past the parking lot to make a twenty mile ride). I hope that the trail does get connected and soon.
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