Find the top rated mountain biking trails in Winchester, whether you're looking for an easy short mountain biking trail or a long mountain biking trail, you'll find what you're looking for. Click on a mountain biking trail below to find trail descriptions, trail maps, photos, and reviews.
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Trail is well maintained, very few bumps, and flat. It's listed as 6.6 miles long but I clocked it at closer to 7.5 miles. I gave it 4 stars because it's not really a very scenic trail.
We (5) Friends Have Biked This Trail in It’s Sections from E. Hampton to Willimantic for Many Years. We Have Always Considered it to be 4-5 Star Rated, (For a Gravel Trail). Since 2015, We Have Switched to E-Bikes which makes the Trail 3x more FUN !! Having the Best of Both Sun & Shady Sections, It Has Only One small Section of about 300’ Near the Start leaving E.Hampton Where it’s sandy & .Loose
Rode on 7-26-25 Needs mile markers at Windham end. Slight incline from Salem to Windham. The Windham trail is paved, but turns to dirt when you reach the Salem trail. Turned around and rode back to Windham.
the Windham trail is paved, but turns to dirt when you reach the Salem trail.
Turned around and rode back to Windham.
rode trail july 28, 25 from Winchendon - slight uphill, going south to Gardner. Adding mile markers would be nice ! and directions at N.Ashburnham Rd to Old Gardner Rd. Newly paved from entrance off
Old Gardner Rd to Gardner town line. Path to avoid watery underpass was paved on one side of street.
It’s a nice paved path, shaded half way through. Good for families with kids. Parking is free but though to find, suggests keep following the path till you find parking. There are several options along the way from the eastern end of the trail. Few food and restroom options, within coffee or mall shops. Public restrooms are very limited at least when starting from east end. We went only half way and back, with kids. Looking forward to finish the second half soon.
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.
It’s my go to trail because it’s so close to my house ! you can walk down close to the river it’s cute . i always get to see ducks in the pond
Wife & I completed the Minuteman Trail & I wanted to do either the Narrow Gauge Trail or the Reformatory Trail. Wife headed for the Bedford library while I set off for the Narrow Gauge Trail. Trail was in good shape & I was prepared for the surface conditions associated with crushed stone. What caused me confusion was a lack of trail markings. I rode for about 20 minutes or so & eventually came to a gate, which was in the open position. I wasn't sure if this was the end of the trail (and still unsure at this point). I looked for signs, etc & saw none. The trail appeared to continue, but it's condition was much less pristine i.e. large ruts and valleys. I rode for what seemed like another mile until I came to a paved road & straight ahead was a paved road with a "Private Road" sign. I exited here & took surface streets back into Bedford. I am giving the trail a 2 star rating; better signage would increase my evaluation.
In Boston area last week for a conference and decided to try out the Minuteman Trail. Spouse and I have been enjoying bike/rail trails over the past few years and usually one of the first things we check out when traveling to a new area. Trail was in great shape & was as good as expected. Being summer, it was pretty hot weather but the trail provided ample shade for us to stay cool. Particularly appreciated the history of the trail, and it's relevance to Paul Revere's late night ride. This was our first time in the Greater Boston area, as we're from North Carolina. All in all, a good ride and fun experience.
A delightful paved trail in excellent condition. Relatively flat with some pretty views of the lake. There is a side spur to Speen Street that connects to the Natick Mall. Great for a quick and easy ride.
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