Explore the best rated trails in West Springfield, 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 54 trails covering 454 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 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...
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 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 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...
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...
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 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,...
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 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 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,...
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...
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 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 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 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...
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 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...
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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...
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 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 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 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 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 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...
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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 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 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 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 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 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...
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 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...
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 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...
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...
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 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...
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 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 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...
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...
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 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 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 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...
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 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 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 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 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 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 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 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...
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 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 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 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...
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...
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...
We finished this part of trail on June 18. All paved. The newest section had interesting concrete panels for bridge decks. Good mix of open and wooded areas helpful on 80 degree day. Great Scenery. Very flat. Would suggest some added signage inside state park where road is used. Also at north end of park no signage to indicate how to get to Hillsdale section.
My son and I did a pre-fathers day ride. Trail was terrible. Many dead birds on trail and not well maintained. Would not recommend. No trail markers, or mile markers.
I was a first time user and started from the trailhead near Keene State after parking in the shopping center lot on Emerald St. The pavement was done after the first 0.5 mile and then after the bridge over the highway the trail became packed dirt/stone. It has been dry so the going was fine and the trail is relatively smooth. At mile 5 the trail becomes a 100 yard stretch of sand as it runs along the road- hard going and I just took the road on the way back to bypass it. After this the trail gets narrower until it is simply a dirt track through a mowed strip of grass along a power line right of way. Around mile 7 there started to be patches of mud which had enough solid surface to get through, the longest was probably 20-30 yards long. I wasn't able to reach my goal of 10 miles before turning back due to a large mud puddle (mostly puddle) at mile 8.7- no way to bypass it due to the overgrown vegetation on each side and more mud than I was in the mood to handle. But I enjoyed the ride, it was not crowded when out of Keene (between 9-11am on a Saturday morning). My bike is a hybrid with road tires and did OK.
We rode from Millerton to Wassaic and back last Saturday. All paved. Very scenic. Flat. Not much bike or walking traffic. Look forward to completing the other way to Hillsdale. Enough shady areas to make this a good trail later on in the summer.
I have done the trail in sections and I have done the entire loop. I recommend doing the whole loop if you can. The Farmington River Trail is quite scenic and offers a mix of closed paved trail, closed dirt trail, trails through parks, roads, and sidewalks. Along the trail there are plenty of places to stop and relax, shop, eat, even play mini golf, there are views of the river, and open areas. In Collinsville there are places to eat or grab a snack. Simsbury offers plenty of dining choices as well, and not far from the trail is the Drake Hill Flower Bridge. The trail along the river south of Collinsville can get really busy especially on weekend afternoons. Overall a great trail but combining it with the Farmington Canal Heritage Trail section that makes it a loop of just under 30 miles makes it a great ride.
The southern section is beautiful along the river. I rode from Simsbury to the Heritage trail. Cinder part is ok. Had a few problems with signage and luckily had downloaded the trail map. I had to stop Often to make sure I was in the right place
Took a bike ride up and down the trail and it’s very well done. Well paved and marked. Very well thought out with port-a potties and stop areas. Highly recommend it.
The day that I rode this trail was a beautiful Spring day and there were various other riders, walkers, runners and, in Northampton, people going for stroll. It is a well maintained trail, not too long, plenty of things to see and places to relax. Part of the trail is rural feeling, but other parts are located right near downtown. A nice mix.
I was pleasantly surprised that trail had been repaved or at least repaired. Most of the tree limbs and frost heaves are now gone. Pretty ride made better by surface upgrade - thanks
Beautiful trails to skate, lots of pebbles near intersections but otherwise clean and smooth.
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