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 Appel Way Trail and Common Pathway. With more than 48 trails covering 332 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

Ashuwillticook Rail Trail

Great trail in MA!

June, 2023 by steve.schwinn

Road the trail last week end-to-end as an out and back from the great southern trailhead parking area on Crane Avenue (bathroom). Trail is in excellent condition and a great ride.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

May, 2023 by earthman58

Beautiful section in terms of scenery and access to lakes and ponds. The surface can be challenging. Today, with fairly dry conditions, it could be negotiated with hybrid bikes.

Delaware and Hudson Rail-Trail

crossing gates are too narrow for a bike trailer

May, 2023 by lauriekeve

We rode from Castleton University to the end of the trail at the New York state line, and back 5/2023. We were able to get our Burley Bark Ranger (dog) bike trailer through the roadway gates with some difficulty, backing up, straightening, trying again. For several miles, this happens every 5 to 7 minutes. Then it gets better. I’m not sure if a two seat child trailer would make it through. There is a Poultney River loop trail that can be accessed from the rail trail, but it’s definitely not for bikes towing trailers like we do. Poultney is very cute, and we saw a pizza shop, and creemee stand there. The surface is great for slightly knobby tires. Bucolic farmland, quiet, sunny ride. One of the multiple snowmobile bridges crosses a river, and it’s a great spot for a shaded picnic and tossing a stick for the dog.


Concord-Lake Sunapee Rail Trail

early spring bike ride

April, 2023 by cantabty

The trail is very well marked with easy parking. Lucky I had my fat bike today for todays ride. Trail conditions changed from dry, wet, icy packed to snow plowing. It was fun to experience all seasons in one day with a bike to handle deep mud. It’s early spring and expected.

Corkscrew Rail Trail

a very straight section

March, 2023 by bob.stijne

There are no curves or bends in this section. Just a straight line. There is a dirt track in the middle. For the kids there are signs with questions which is nice

Mass Central Rail Trail

Weston part not the best for rollerblading

February, 2023 by 7q2vdb7mbx

The pavement is decent, but there’s no marked center line. Biggest complaint is that the trail primarily goes downhill as you go east, and primarily uphill as you go west, so you’re going to hate one direction or the other. Decent views. Poor road-to-trail transitions with broken up pavement and sand which is a nightmare for in-line skates. Much prefer the Cochituate rail trail

Twin Cities Rail Trail


February, 2023 by caddydvr

Love this rail trail !! Nice easy path , street crossings are easy to get thru. Great job by both cities.

Ware River Rail-Trail

Great if you like exploring, like I do.

January, 2023 by alan113

Rode (7/22) from Winchendon to Baldwinville, and then (skipping the part bisected by Rt. 2) from from Rt. 101 in Templeton to Route 122 in Smithville on the Barre/Oakham line. Lots of wet and rutty sections north of Balwinville but still fun (some walking with 1.5" tires). Some sandy section in the southern piece but still fun. It's slow going of course. Didn't pass a single extra person. Good roadside fried food at Lee's in Baldwinville (it's been there for at least 70 years!)

Ashuwillticook Rail Trail

Excellent ride- one of the best trails!

November, 2022 by billmeredith58

We rode the Ashuwillticook Trail on 11/07/22 from the Pittsfield trailhead to Adams and back. The ride is excellent, with plenty of scenic highlights along the entire route, smooth paved surface and many places to stop and enjoy. The towns along the route looked inviting enough to divert us, but we had time constraints so we stayed on the route. The head winds on the way back were a challenge..
This is one of the best trails we have been on, not to be missed.
PS Recommend enjoying a long weekend and stayed at a B+B in Lenox...

Note: the restrooms along the route were all closed. I can understand given the time of year but it seemed somewhat premature given the warm weather we had been experiencing.

Canalside Rail Trail

Bonus! Bonus!

November, 2022 by egauger

Nice trail, what it lacks in length it makes up for in bonuses. 1. Brick and Feather Brewery along the path with outdoor seating. 2. Discovery Center Museum near trailhead in Turner’s Falls, free, cool animal displays and lots of interesting information in this little gem.

Fort Hill Recreational Rail Trail

I agree with previous reviews

November, 2022 by slasalle76

After riding the Ashuelot Rail Trail in the summer and seeing this from the parking lot on Rt 63, I came back on an unusually warm November weekend to give it a try. I fully concur - this could be a gem of a trail if a bit more work could put in, but still a nice enough ride. I was on my hybrid, and am beginning to wish for a Fat Tire or maybe at least a shock absorbing front fork for these jouncy pot-holey trails. Pity that the trestle is falling to ruin, and in the slight rain I was caught in, I didn't chance it with slippery sneakers. Frankly, it's a tragedy waiting to happen, and with as many rotted rails as there are, I was surprised to see 3 bikers walking gingerly across. Kudos to the snowmobile clubs who watch over this trail, as you could see where chainsaw work had been done to keep it open.

Ashuwillticook Rail Trail

Beautiful Trail

October, 2022 by lexonyskiddiecollege

We decided to go when the leaves were just starting to change color and fall. What a great time to go. So many awesome photos we were able to take. The trail is such a relaxing place to enjoy the outdoors. We were only able to do the first section from Crane Ave to the Berkshire Mall entrance. Took us about an hour to leisurely walk that distance before it started to get dark and we had to turn back around. I’m hoping they will decide to put some kind of lighting through out the trail. Otherwise, it’s nice and clean, pet friendly and plenty of spots to rest and take the scenery in and get a few photos. I feel like we will enjoy this trail more now that the crane Ave part is completed.

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