Explore the best rated trails in Great Barrington, MA, whether you're looking for an easy walking trail or a bike trail like the CTfastrak Multi-Use Trail and Charter Oak Greenway . With more than 59 trails covering 816 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 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 biked on a Sunday in May. Plenty of parking at West Hurley. The scenery was stunning and varied. Started in forests, with some reminders of people who made their living in these woods. Ended with views of Catskills and the reservoir. Truly stunning views, wide, well maintained trail that we cycled on our hybrids.
Rode a portion from Milldale north to Southington. All paved in fairly decent shape. A few bumps but no broken pavement. At the point in Southington the trail just ends with no information as to where to go. No signs or arrows. The trail picks up somewhere a few miles away but I couldn’t find out how to get there. On the portion I rode it was flat and easy, but not much to see other than woods and backs of buildings.
.With a mix of cinders , gravel , dirt & pavement this makes for a nice interesting ride . Along the way in High Falls make a left and visit the D+H canal museum its about a mile down the road . Once you venture a mile and half through a grass area the trail stops however pedal straight out on to Lucas tpk & make left onto 209 then left on main & right on scenic you will then pick up the trail to accord
Had a great evening bike ride out at the Windsor Locks Canal trail earlier this month (Aug, '25). The trail is paved, and as others have mentioned, it is not super smooth in some areas where the tree roots are pushing the asphalt up but can be navigated pretty easily. I was riding my gravel bike setup with 42mm tires and was able to go quite fast - averaging 15mph on the ride so it really was not that beat up / bad.
The scenery on the river is very nice, and the canal on the other side was also fun - lots of wildlife to see. Would recommend if in the area!
Rode the entire Farmington Canal Heritage Trail as part of a 2 day ride from Northampton to New Haven. What a fabulous experience! So much variety and New England splendor packed into one journey. It was very interesting to see how each of the towns maintained the trail differently. Everything from the paving to the signage changed as you moved from one village to the next. What an amazing treasure!
Short for bike, nice views, benches and even a real train.
Yes Walkway is wonderful, just one problem Cyclist Courtesy.
Have rode and seen a lot of cycling after 60 years, but never the lack of cycle courtesy that takes place on Walkway. Cyclist not letting one know that one is passing on left, or better yet on right, speeding, limit is10 mph. This is not just happing to slower cyclist but also when passing pedestrians. This also applies to the new E Bike presidents.
June 6th 2025
The Mrs and I rode this beautiful trail from North Hampton to just short of Belchertown, and back.
The weather was great and the trail is mostly shaded, so the ride was superb.
I'd have no objection to doing it again.
Settle grade difference between start to finish. All paved smooth.No bugs.Crowded with walkers, skaters, and bikers.Windy in the afternoon.
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