Looking for the best trails around Brattleboro?

Explore the best rated trails in Brattleboro, VT, whether you're looking for an easy walking trail or a bike trail like the Warner Rail Trail and Bagley Rail Trail and Sugar River Trail . With more than 49 trails covering 358 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.

Recent Trail Reviews

Canalside Rail Trail

Alongside the canal, an easy ride

May, 2024 by davidcareyvermont

I took my bike over the Canalside Rail Trail while my wife shopped at BJ's, and it was a perfect opportunity to check out this lovely short trail. For the 22nd April 2024, the weather was really good yet there were only few other walkers on the trail at the same time. I was able to park at the southern, McClelland Farm Road, end of the trail where there are only half a dozen spots, but there are many more parking spaces at the northern end.
The trail was in more than satisfactory condition and the signage was also nicely in place, not that it was really needed. I didn't have time to stop in at the Discovery Centre Museum but I did return to BJ's in plenty of time to pay for my wife's shopping that day. I had a lovely time so much so that I plan to take my wife on the same trail whenever I get my old tandem up and running.

Sugar River Trail

amazing Trail

April, 2024 by nariipr

We had a great time on this trail, which was easy to navigate. It was our first outing this season since we acquired an ATV for my wife and we enjoyed spending time together while exploring nature. We encountered people walking their dogs and bikers along the way. The trail was well-maintained and clean. We made sure to slow down and say hello to everyone we met. We will definitely be back on this trail again!

Canalside Rail Trail

You can expand your ride…..

March, 2024 by basil1986

I love this trail! Rode it on 3/14/24 when weather was 62 degrees. This trail is short but can be expanded if you cross the metal bridge by the brewery and take the road to the left leading to the Fish Research Hatchery on the opposite side of the canal. If you meander through the little neighborhood on that side as well you can extend it further and get another view of the old mill complexes. I get 20 miles out of the ride. Bring a lunch there are picnic tables on both sides!

Accordion

Ashuwillticook Rail Trail

Not ADA compliant

February, 2024 by ljt trike rider

It looked very nice from the parking area, but could not get through the barricades with a recumbent trike. Drove over an hour and gates were shut and would have had to lift trike over gates. Disgusted with Massachusetts and whomever designed the barricades. Has anyone heard of the ADA?

Ashuwillticook Rail Trail

Great fall ride.

November, 2023 by cantabty

Excellent experience on this fresh paved trail. The scenery of the ponds and mountains in the distance was worth the trip.

Stevens Rail Trail

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

October, 2023 by imaginetravelsgd

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

Cheshire Trail South. Rode north from State Line Circle toward Kenne. We are experienced road cyclists, now riding gravel bikes. We are looking for reasonably surfaced longer trails and hoped this would be one of them. Sadly, we found this trail to be rocky, rutted, with lots of roots, and uncleared blowdown. The vigilance required to remain upright made it difficult to enjoy the beauty all around. The suddenly occurring steep inclines to roads seemed borderline dangerous. If we lived closer it would be a great trail to walk with the dogs

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

just walked the D & H trail from granville center to middle granville. really enjoyed the walk out toward middle granville but on the way back while walking through the farm (which was a delightful experience on the first trip through, seeing calves and cows) but then were charged by two pitties which attacked my dog and knocked me down. Luckily I had an umbrella and was able to get up and get away and down the trail. the dogs followed for a while but then returned to the farm. Too bad because was a very enjoyable walk until this. I just hope these two dogs dont really hurt someone....

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.

I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.

Please put this one on your list to help!!!

Ashuwillticook Rail Trail

Good scenic ride

September, 2023 by richmedcraft

I rode the trail from Pittsfield to the end in North Adams and back on 8/5/23. The trail is paved and in good condition and restrooms at the Pittsfield trail head were clean and working fine. Nice scenery including lakes and the Berkshires- I was able to finally identify Mt Greylock after the morning clouds had dissipated. The grade is gentle and I was able to keep up a consistent pace for the ride.

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