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 52 trails covering 448 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 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 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 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,...
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...
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...
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 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 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 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...
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 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 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 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 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...
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...
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...
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 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,...
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...
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...
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 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...
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 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 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...
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 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...
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 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...
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 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 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 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...
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 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 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 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 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...
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...
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 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 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 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...
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 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...
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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...
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...
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 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...
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 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 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...
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...
My actual rating on this one is 2.5 stars. One glorious day, probably in a couple of decades, this will be an amazing trail. Right now, it is an extremely mixed bag, and very challenging to do all the way. Me and the friends I rode with didn't make it to the end.
We started on this one as a continuation of the Air Line State Park Trail in Connecticut, heading from west to east, with the Forge Park/495 train station as our destination. The Douglas portion of this one was fine; none of it is paved, but it's maintained, free of ballast and standing water, and our bikes (one loaded tourer and two old-fashioned/90s mountain bikes) were fine on it, if not quite as fast as they would be on asphalt. There was very little traffic; most of the way was reasonably shaded, and the grades are gentle. At some point in Douglas State Forest, it starts skewing downhill, but not really enough to be noticeable. I probably wouldn't take a road bike on it, but a decent all-purpose bike should do fine.
Things became a little harder in Uxbridge. The trail got narrower, rockier, with some overgrowth. There were some pools of standing water, felled trees, the occasional stretch of ballast, and a few above-grade road crossings (i.e., steep hill to the road, then steep hill to get back on the trail), and heavy damage from ATVs. I, on a touring bike, was able to negotiate it, but I had to *negotiate*. And, more than once, walk my bike.
Things continued to be mediocre-to-challenging as we we approached Route 146. At the highway -- which is an uncrossable, shadless, multi-lane freeway -- the trail became complete garbage. We waded through deep pools of standing water and fought our way through fetid, swampy overgrowth before the way basically just disappeared. We had to ride *right* next to the highway itself for a short distance to find a steep, rocky little side path that drops you onto a surface road.
According to the information we had, the trail could be reacquired by riding through some nearby industrial parking lots, but this turned out not to be the case. Thank Cthulhu for Google Maps, because it seems you actually have to detour about a mile on the local roads, which are wide, fast, and without shade, in order to find the entrance to the Blackstone River Greenway, which is the next stretch of the trail. There is next to no signage for any of this.
After the mess that was Uxbridge, the BRG was *exceptional*. Smooth, shady, not heavily trafficked, and some beautiful views from river bridges. I enjoyed every single foot of it. Unfortunately, it dead-ends at a bridge that's still under construction. We needed to leave the BRG anyway, since it will ultimately connect to an existing trail in Rhode Island.
Returning to surface streets, there was no sign of the trail at this point, so we consulted Google Maps again and went up Castle Hill Way, which is a subdivision of condos, devoid of any indication that the trail's right-of-way is there. You have to ride up the road and then go through a little grassy area to get to the gate where the trail picks up. It was doable, but rocky and overgrown, with pockets of ballast and standing water, and stretches damaged by ATVs. Fun for mountain and gravel bikers, maybe, but not so much for us. There was a fenced-off road crossing, but we could maneuver our bikes around it.
The trail continued to be in poor condition, and eventually, somewhere in Bellingham, we ran into a long section of standing water and ballast. Amid the bugs, the heat, and the horrible, nearly impassable terrain, we decided we'd had enough and exited onto Old Elm St., taking the road the rest of the way. Had we gone another mile or so, we would have reached Center St., which we'd heard is where the trail becomes a smoothly paved path all the way to Grove St. in Franklin. We did pass an intersection with the trail on our way to the train station, so that seems to be correct.
So, as I said, this will be an incredible bike path one day. For now, except for the Douglas section, the Blackstone River Greenway ,and the paved section in Franklin and Bellingham, it is best used by people with strong mountain/gravel biking skills, and equipment to match. The painful parts are just not worth it.
Rode most of this one with some friends, picking it up in Danielson. Finding it was a tad tricky, but maybe that was related to where we picked it up. Once we got going, we really liked it. Smooth pavement, very well-shaded, and right next to a peaceful river. Absolutely wonderful after a long day of riding in near-90 degree heat. I wish it could have gone on longer.
This is a nice (mostly flat) trail that is paved from the road behind the Clark YMCA all the way to 140. There is a short on-road section with a decent uphill to pick up the trail over by Rt 140. Past 140, the trail alternates between sand, gravel, and loose rock on one uphill. Trail suddenly ends at a barrier that’s the edge of a cemetary.
I rode this trail out and back on 7/15/2021. Total out and back ride clocked in at 9.55 miles, 150 feet elevation change down heading North, so 150 feet uphill heading back South. I parked in the shopping plaza by the Taco Bell and rode the bike lane to the CTfastrack station where the trail starts.
For the most part the trail was clean except for a broken bottle just outside the first station, and a couple of trash cans that were left out for pickup on one of the sidewalk sections. There were not many people on the actual trail and every single one of them said hello and or thanked me for signaling when passing. The trail parallels not only the bus lane, but also an active train line, Amtrak is doing work on the line so in some places you can smell the new ties that they are installing. On the north end of the trail I stopped at a Dunkin' that was across the street from the station, and at the south end I stopped by the bike shop that is next to the hotel and part of the parking garage. There is a mix of businesses along the trail including convince stores and places to get food. The scenery is a mix of urban, industrial, tree lined, train tracks, and bus depots, if you pay attention you will even see a fiberglass Cobra Shelby along the sidewalk section. You will see plenty of busses, and if you are lucky maybe a train.
[Biked from Bushnell Park to Charter Oak Park and back, 7/11/21]
If you're driving to a trail, don't make it this one. As many have said, the experience of biking next to the I-384 is less than stellar. There were two places where the vegetation had overgrown the trail to the point where some cyclists are going to crash sooner rather than later. The trail is boring, the street portions are boring, there's really nothing that makes this trail stand out. If you don't want to see people but you want to hear cars anyway, this might be the trail for you. Hardly anyone else on the trail, must be that everyone else is wiser than I. Aside from being a boring, noisy trail with occasional Jumanji hazards, the pavement itself is in decent shape and the hills give a workout so I'll refrain from giving this 1 star.
I won't blame this on the trail given the recent storms, but there was also a downed tree blocking the entire path and the only way around was a muddy, flooded detour some intrepid souls must've carved.
Also protip: Labyrinth appears to be closed on Sundays, I'd call ahead if you're planning a beer with your ride :(
I like this trail to walk because it is well paved, flat, no hills, and friendly considerate people especially the bike riders who usually indicate when they are passing me. There is some industrial and kind of dumpy areas that abut the trail unlike where I came from, Woodstock NY, where the paths are pristine and beautiful. However, I like where the trail crosses a bridge across the Mill River just past Veterans Field in Northampton.
This is a great ride for me to test my novice skills. I find myself coming back to here twice a week after work just to get a quick workout in
Started at Prospect Street boat launch and road north. First mile or two of trail is wide and gravel with potholes. Nice scenery next to river. I'd score this part of the trail a 3. From mile 2 to 3 the trail is still wide but mostly grass with two dirt tracks (a car width apart). Grass is about 8 to 12" tall. Hard to see some bumps and defects. I'd score this part of the trail a 2. From mile 3.2 to the bridge at mile 4.4 (all distances from Prospect Street) boat launch the trail is in poor condition and a single track. I'd score this a 1. The bridge is the remnant of an impressive structure. The steel is rusty but in good shape. The timbers are rotting but for those not intimidated they can be walked. It's a shame the bridge isn't being saved for rail trail users. This is a dead end. I wanted to get back on to Route 119. I needed to go back 1.2 miles to find a poor quality side trail that dumped me out behind the Sunoco gas station.
The scenery on the ride was the best for the first 2 miles of the trip. After that, in general, you are inland and not looking to the side. Your focus is on navigating the trail.
We just rode this trail for the first time and we will certainly be back. Amazing views, paved surface, and plenty of opportunities to stop and sit. The only improvement I would suggest would be to add mile markers.
I went from West St., Uxbridge, MA to the Connecticut boarder, it was around 8 1/2 miles on the way and over 16 miles round trip. Nice ride, saw 1 horse along the ride along with a few walkers and bikers.
Easy access and very flat and straight. Nice trail to cycle for couples and families.
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