Find the top rated trails in Westfield, whether you're looking an easy walking path or a long bike trail, you'll find what you're looking for. Click on a trail below to find trail descriptions, trail maps, photos, and reviews.
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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 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...
As of January 2012 the Quinebaug River Trail has two segments. The southern segment follows the course of the Quinebaug River in Danielson, beginning at the intersection of Palmer Street and Prospect...
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
The North Central Pathway will one day stretch 16 miles between the cities of Winchendon and Gardner in northern Massachusetts, primarily along a former railroad right-of-way. Three open sections...
Note: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....
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...
Nestled in the Hoosic River Valley, between Mount Greylock and the Hoosac Mountains in Berkshire County, the Ashuwillticook Rail Trail takes its name from a Native American word meaning "the pleasant...
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 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...
Harlem Valley Rail Trail provides a scenic ride through rolling farm fields and dense woods on the bed of the New York and Harlem Railroad that ran from New York City to Chatham. The rail-trail is...
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...
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Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
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 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...
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 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...
Canalside Rail Trail begins at McClelland Farm Road in Deerfield and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately a...
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In central Massachusetts, the Norwottuck Rail-Trail (formerly the Northampton Bikeway) runs between New South Street in Northampton and the neighborhood north of Look Memorial Park in Florence....
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...
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 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...
Grand Trunk Trail is part of a larger trail network, the Titanic Rail Trail, which will stretch more than 60 miles through south-central Massachusetts and the northeastern corner of Connecticut along...
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 North Central Pathway will one day stretch 16 miles between the cities of Winchendon and Gardner in northern Massachusetts, primarily along a former railroad right-of-way. Three open sections...
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...
The delightful asphalt Middlebury Greenway winds 4.5 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
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 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 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 Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
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...
As of January 2012 the Quinebaug River Trail has two segments. The southern segment follows the course of the Quinebaug River in Danielson, beginning at the intersection of Palmer Street and Prospect...
The Sue Grossman Still River Greenway runs for nearly 3 miles through a wooded corridor between Lanson Drive and Harris Drive in Torrington. The paved trail occupies the old right-of-way for the New...
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The Blackstone River Greenway (previously known as the Blackstone River Bikeway) is a 3-mile trail that represents the first open segment of the Massachusetts portion of a pathway that will eventually...
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Thanks to skilled engineers with the former Hartford, Providence, & Fishkill Railroad, the pretty Vernon Rails-to-Trails overlooks ravines and streams and passes between rock walls verdant with ferns...
Note: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....
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...
Canalside Rail Trail begins at McClelland Farm Road in Deerfield and heads north on the former NYNH&H Railroad, crossing the Connecticut River near its confluence with Deerfield River. Approximately 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,...
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...
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...
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 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 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...
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...
Canopied with deciduous trees for most of its 10.8 miles, the Larkin State Park Trail (a.k.a. Larkin Bridle Path) is primarily a wilderness trail, with wooded vistas, wetland views and sparse...
Stretching east from Northampton, the 10-mile Norwottuck Branch of the Mass Central Rail Trail connects the towns of Northampton, Hadley, and Amherst. Part of the Connecticut River Greenway State...
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 delightful asphalt Middlebury Greenway winds 4.5 miles through the residential community of Middlebury, connecting businesses, parks and neighborhoods. The popular trail offers residents an...
The Bridge of Flowers is a 400-foot-long former trolley line bridge that has been converted into a garden pathway. Open from April 1 to October 31, the bridge spans the Deerfield River between...
The Blackstone River Greenway (previously known as the Blackstone River Bikeway) is a 3-mile trail that represents the first open segment of the Massachusetts portion of a pathway that will eventually...
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 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 Manhan Rail Trail wends its way between Easthampton and Northampton, with a spur trail leading out The Oxbow near Mt. Tom. Easthampton is a typical New England factory town brimming with commerce...
Note: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....
The Kress Family Trail follows an old rail bed of the former Shepaug Railroad, which winds along the Shepaug River. The flat, out-and-back trail is popular with cross-country skiers and snowshoers in...
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...
We have ridden this trail before, and really enjoyed it, especially the part near the ponds below Oxford Airport. We expected it to be somewhat rough, and we are always willing to walk through particularly wet/mucky areas and to put up with rough stretches. However, the trail has really gotten much worse. After about 2-2.5 miles in, it became extremely sandy/silty, and we could only ride on the narrow edges. Then at about 4 miles in, there was a stream flowing through the whole trail, with nothing but mud and muck; no way to ride through, as it continued as far as we could see, so we had to turn around. End of ride for the day...
I love walking this trail. I have yet to make it to the end with the kids as they get tired we have gone most of the way. I walk there a few times a week with them. They love seeing the turtles in the water. Only thing I dislike is those who dont clean up after their dogs. I have stepped in dog doo on the trail, and alot of those who do clean up throw the colored baggies in the bushes so you always see colored bags oi n the ground and un the tree.if your not going to take the bag with you then leave the pool it will eventually go away your bag on the other hand will go nowhere :(
Looks like the bridge over Rt 6 in Bolton is finally going in. Connection to the Hop River Trail this Summer?
I’ve been walking the millbury Worcester trail since it opened. It’s so sad what’s become of it. Loaded with trash and broken glass. The trail is now under construction to include a center and lengthening the trail! Why bother if it’s not going to be maintained.
Just got my new gravel bike and this trail was a perfect bridal (horse) trail ride.Mud ,cinder,dirt and gravel are what you will encounter ,but the high berms,ponds and deep woods experience are worth the trip!
When I rode it in September 2016, it stopped a short way into the town of New Lebanon, dead-ending before it reached the village. It's a nice ride as far as it goes. Hopefully it's now as long as the map says it is.
This trail is beautiful in the fall. Well maintained and mostly paved. Its a smooth ride but gets a bit rocky crossing between bolton and vernon. Other than that this trail is amazing. Can be a bit crowded on weekends though
After heavy rain on April 16th, the trail along the Willimantic River is temporarily flooded and impassable,
I am fairly new at skating, so I am always on the lookout for nice trails to try. Near the park itself, the skating is great. It is fairly smooth, has nice wide paths, and only a little bit of hill. As I went further from the main park however, it was almost entirely up hill, and there were several bridges that may not be too bad normally, but they are rougher and have lips that prevent just coasting onto them. On this particular day it had snowed recently so while the paths were dry, the bridges were covered in slush and very hard to do anything but carefully walk on while holding the railings. It took me a long time just to go half a mile because of the slope and bridges, and then when I decided to turn around, the hill was so steep, I frequently had to go into the grass to avoid going too fast. Normally I would just ride hills like that out, but the path was rather curvy, and there always seemed to be a rough bridge at the bottom. My brakes were useless. If you are an advanced skater, this may be a fun challenge, but for me, it was more trouble that it was worth. Nice park/trail for other purposes though.
I have used this trail for many purposes. First off, I love finding dog parks and having one right on this trail is a great asset. While it is not my favorite, and dogs being there is rather hit or miss most days, it is still functional for what it is and my dog enjoys going there before or after our walks. There are also a few places where the dogs can access the water if they are into swimming.
Second, it is a pleasant walking trail that is both scenic and urban. It leads from the dog park, follows the river, and into downtown Putnam where lots of shops, restaurants, and more await. As a dog trainer, I highly recommend the trail because you get all kinds of training done in one location (dog on dog greeting, urban walking, trail walking, and socialization with all kinds of people and places).
Also, I recently took up Inline Skating, and this trail is perfect for it! It is smooth all the way, and while there are a couple hills, they aren't very hard to go up or down. I couldn't be happier with my skating experience here.
Lastly there is always a lot of available parking at various points along the trail: at the dog park, near two river access points, near picnic areas, near a band stand, and of course in downtown Putnam itself. It is so convenient! I love this trail and visit it often.
It's a fantastic trail. I went after a snowstorm a few days after and to my surprise the trail itself was nice and clean, snow cleared! It runs along the Quinebaug River and it is a very peaceful place for a walk. I have not completed this trail seeing how we just started walking but will look forwarded to completing this trail. Great place for a bike ride, Walk, Run, skate, strollers. All paved once you get to the trail.
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