Find the top rated horseback riding trails in Massachusetts, whether you're looking for an easy short horseback riding trail or a long horseback riding trail, you'll find what you're looking for. Click on a horseback riding trail below to find trail descriptions, trail maps, photos, and reviews.
The trail is poorly maintained. Do not recommend.
We took our bikes over to Marthas Vineyard on the Steamship Authority ferry out of Woods Hole on May 5, 2026. We had parked for free 3.5 miles up the on the Shining Sea Bike path in Falmouth. We landed in Vineyard Haven at 11:30am and made our way from the ferry to the Forest Bike loop. It was 3 miles from Ferry to the path. We walked our bikes for the first half mile to get out of the downtown traffic as the sidewalks were quite narrow. Once we got rolling it took us about half hour to get to the start. Once on the path it was quite easy to follow the loop. We went past the airport and many fields and secluded homes. We brought our own food and water, but there was a convenience store at the airport on the first stretch on Barnes road. It was about 63 degrees out with stiff winds of 20+ miles per hour that the trees helped to minimize. The path was good in most places with some cracks in the asphalt that we tried to navigate around. Some rolling hills along the way, which we walked up a couple to avoid over doing our knees. It was a beautiful Tuesday afternoon and we only saw one other bike and 3 people walking in our 10 mile loop. The ride back to the ferry was far easier than the ride out as it was mostly downhill. I rated the ride a 4 of 5 only because it was a bit difficult to get from the ferry to the bike path, other than that it was a great paved trail.
The surface is paved, and in excellent condition.
The trail is ever so slightly down hill from north to south.
Mostly shaded, and while not amazing scenery, it is a lovely trail. In spring, when sunny, watch to LOTS of turtles on the far bank of a swampy section near the cheshire reservoir (on the west side of the trail)!
Starting at the Town Hall, the first half mile is on busy Route 113. There is a marked bike lane on both sides, but the sidewalk was not good for my recumbent trike and the road twists and turns, so visibility isn't great. I'll skip this part next time. At the half mile, Route 113 turns away and the trail goes along the river on a little traveled one way street. At a little over a mile, it's back on a two way street that has good visibility so it feels reasonably safe. As noted above, at 441 Main Street, the trail turns left onto a railroad roadbed, which is now a power line right of way, and continues southeast for almost two miles, with two road crossings. This is wide asphalt in excellent condition.
Although there are empty woods on the west side for much of the two miles, this is not a wilderness trail. I think there was at least one building in sight for the entire time.
In addition to parking at both ends mentioned above, there is parking at a National Grid facility at 452 Main Street, right at the head of the railroad trail.
The trail is now wide asphalt in excellent condition, with clean, well groomed sides. Most of it is very close to the river, so, while foliage may obscure panoramic cross river views, it's still pleasant for a downtown trail.
Park at Circuit Street for very easy access to historic sites. There are many interesting things to see at this end including the 1829 West Hanover Cemetery and beautiful water features at this end. Recommended.
First, be aware that the description is not accurate. The north end of this trail, from the dead end near I-95 to 2300 feet south of Pye Brook Road (PBR) is in Boxford, not Topsfield.
The portion north of PBR is a single rut, usable, but not great. From PBR south to the Boxford-Topsfield border it's a little over a yard wide, packed fine stone, not quite as firm as asphalt, but perfectly satisfactory for my trike. At the border, the trail becomes a single rough rocky track, barely usable and very uncomfortable on my trike. I can't comment further south, because I turned around.
The Canalside rail trail is fully open and the paved trail is very well maintained. While it is only 7.2 miles round trip, it’s worth it! Plenty of parking at both ends and the town of Turners Falls has a nice selection of restaurants and shops.
We’ve biked this many times. It quickly takes you from Lowell, with its National Park, etc to countryside and the center of small towns along smooth, paved, well-maintained trail. Nice to swim in Hart Pond, too, in season, on return trip to Lowell. Trail keeps getting better and better, great facilities along the way as trail is extended.
Perfect place to ride for a beach day/ride. Explore the full state park and triple your mileage. A lot to see. And enjoy the ocean.
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