Explore the best rated trails in Deerfield, MA, whether you're looking for an easy walking trail or a bike trail like the Common Pathway and Appel Way Trail . With more than 52 trails covering 443 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.
I live in Massachusetts about 25 minutes from this trail, my absolute favorite trail is the East Bay bike path, but that is about an hour drive for me, so this is one I frequent more often. I like the length of this ride, and that it is scenic, and more interesting than some of the rail trails that can be kind of boring. I think it is an easy ride, with just a few spots I need to lower my gears. I pack a lunch, snacks, and can be out for a few hours. There is ample parking, 195 Davison Ave Woonsocket is the address I use for WAZE. I have never gone as far as Providence, so I can only review Woonsocket - Lincoln.
Haven't ridden the trail since 2023. Rode from Cheshire down to New Haven, Saturday July 19th. Absolutely awful; entire section needs repaving and upkeep. Constant cracks in pavement and much debris on surface; plus glass and homeless down by the Wharf. Connecticut should take notice from Mass and NY on trail up keep. Both states's trail are far superior to CT. Also, difficult to navigate at trail end in New Haven if you don't know the city; poor signage.
I have ridden this trail from one end to the other! Parts are wonderful and parts washed out and muddy!
Beginning perhaps 2 miles north of the Simsbury Airport and continuing north for at least a few miles the trail will be closed for construction (looks like repaving + ?). I was on this trail yesterday and the "Will Be Closed" signs are abundant.
Love the scenery. There are plenty of rest areas.
I rode this trail from the Northern tip south about 10 miles and back. It was very smooth pavement, a well marked trail and delightful views.
Rode it Friday. The views were beautiful, the trail was in great condition, and the road crossings were not a problem at all. I’ll definitely be riding this one again.
I just rode the trail from Cheshire to New Haven Harbor. It gets confusing because of the lack of signage once you go under the Temple St Garage in New Haven. You get dumped out into a street and don't know where to go. The trail is on the road or sidewalk depending on what you prefer. Take a left onto Grove St. continue to the end and take a right onto Olive ST. Follow Olive St. to the end and pick up the trail again on Water St. Cross Brewery ST and take a right to continue on Brewery. Brewery changes to Sargent Drive. Take a left to go under I95 and the water will be in front of you. If you take a right and continue down for a little, along the water's edge, you will find dozens of food trucks to buy lunch before a return trip. It was well worth the trip.
This portion of the Cheshire rail trail has almost no incline is completely straight and runs past a former major manufacturing complex, which is now vacant. Other sites include Keene police department and Keene ice and American house.
As of 6/3/25 this trail is still closed south of 11th street.
There is a detour indicated, which we tried to follow, but quickly lost track of.
Found another way to access the trail further south, only to realize that we'd gotten onto the part of the trail that was officially closed.
I'm sure this will warrant a higher rating once it has re-opened, but we were more than a bit disappointed today.
Start at the Peterborough Shopping Plaza parking lot. Stop in the Information Center across the street. It's operated by very nice local volunteers. Make your way north though the center of Peterborough. The surfaces are mostly paved & packed. You don't hit dirt & gravel until the upper half of the trail. Most riders stop at the school bus parking lot on Rt.202. There's a small parking lot there. If you cross the road you can pick up the Powder Mill Pond Rail trail and follow it northeast for another mile or so until it ends at Forest Rd. The trail gets rougher the further north you go but it's VERY manageable for most riders.
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