Explore the best rated trails in East 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 49 trails covering 436 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 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,...
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 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,...
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 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...
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...
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...
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 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...
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...
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 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 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 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,...
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...
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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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...
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 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...
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...
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...
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...
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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...
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 Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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...
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 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...
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...
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...
More than a mile of the Ashburnham Rail Trail opened in 2015 from a point just south of Ashburnham's center to Turnpike Road. The rustic route, planned to be paved in the future, offers a...
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 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...
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,...
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...
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...
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...
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 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 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 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...
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...
The Washington Secondary Bike Path offers just over 19 miles of paved trail from Cranston (Providence’s southwestern neighbor) to Coventry. The rail-trail, Rhode Island’s longest, follows the former...
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 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...
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 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 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 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 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...
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...
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...
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...
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...
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...
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...
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 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...
We enjoyed this short path to cap off the weekend after having ridden in the cape. Loved the train stop building, wish you could go in and read up and see pictures of the history; instead they had picture signs dotting the ride. Also there were some stone benches along the way and a bike shop I’d say at the halfway point. We saw bunnies too.
I rode this trail on 7/12/19 from Moosup, CT east into Sterling, CT. The first 5 1/2 miles are unimproved rail trail, good for MT bikes or aggressive hybrid riders. At the route 14A crossing I found some improvements underway, 1.5 miles of bull dozer work to a bridge under construction just past Carbuncle Pond WMA. The surface was soft and broken and very hard to ride. This leads me to believe that Road Island has a project underway to extend the Trestle Trail from Log Bridge Road (the current end) westerly to just west of the CT line at Route 14A. I will explore the area in the late fall to see how work has progressed. There is a second bridge in the Village of Green, RI that needs work, but I did not get that far.
Tuesday July 09, 2019, 5:30 pm.
Weather 88' F, low humidity, very light clouds.
Great weather for riding this great trail. Massachusetts really sets the bar for bike trails. This one has a line down the middle to help the careless riders better their performance. There are benches near view spots with poems and examples of flora and fauna carved into boulders. There are granite mile markers on both poles and pavement stones at the side of the trail. The pavement was very smooth and there are only some slight inclines. Tunnels and bridges, a variety of scenery, this is both a community trail and a destination trail. I drove 2.5 hours for this one and the much shorter Canalside trail a half hour away in Turner Falls, doing both on the same day with a mid-trip visit to the Bridge of Flowers in Shelburne Falls. All 3 places worth the trip, but now I have to complete the other sections of the Mass Central Greenway. Good job Massachusetts!
Tuesday, July 09, 2019. Weather 88' F, few whisps of clouds, and low humidity.
It was a great weather for riding and a great trail to ride. The photos here are exactly what you see, except for the very nice park at the beginning of the trail. The village of Turner Falls is quite nice to visit also.
Only 15 minutes away in Shelburne Falls is the Bridge of Flowers, which is a beautiful short walk with a pub at one end. Combine these two activities into one great outing.
I parked at 15 Spring Lake Road in Sterling. A very brief portion is paved, up to the bike overpass, then its mogul after mogul. Great for mountain biking, not so much for hybrid or road biking. Sand, gravel, muddy bits...unkept. Beautiful area, share the trail with dirt bikes and at atvs either direction.
This trail was nice and flat. We got misdirected when we came to the main rd. The bike route follows straight across but we got confused as the sign said road closed, bridge out- but that was exactly where we needed to go. Then you turn to the right and follow thru old brick buildings that are mostly un-occupied. There is road crossings as others stated and they are marked. The cool trestle bridge was a nice view of the river. Past the bridge is a straight way then a few turns as you go slight uphill before it ends at the rail yard. There is a few picnic tables an benches along the entire bike route. Weather was good and cloudy also a nice breeze or it may have been hot along the open canal. We brought the kids to the amazing playground after. There is also a skate park too and you can fish as we saw ppl do- I assume state license needed; we were from CT.
very nice 5 mile trail. great for walking. surface is rather bumpy even on my hybrid. can't beat the views. lots of wildlife.
Long Wharf to Yale is partially on-road, busy and tricky. Agreements with landowners have been completed and future construction will eliminate some of the on-road. 2018 trail completions in Cheshire and Southington make the trail continuous for 23 miles.
The remaining section in Southington is scheduled for construction in 2020. The Plainville section is currently in design. Construction could start in 2021. It might be phased, so construction might be complete in 2024 or later. When the Southington section is complete it will be relatively safe to ride on-road across Plainville.
From Northwest Dr on the Plainville/Farmington border the trail goes continuously to Main St Westfield about 34 miles. A few railroad bridges in Westfield have to be rebuilt to complete the trail to the Westfield River
North of the Westfield River the railroad is active. The best on-road routes include hilly and traffic. In Southampton the trail will be on the abandoned railroad right of way, but the right of way has not yet been purchased.
Getting to the trail in Easthampton requires about 10 miles of on-road. The last 7 miles of the trail to Northampton are complete
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.
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.
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!
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