Explore the best rated trails in Bennington, VT, whether you're looking for an easy walking trail or a bike trail like the Appel Way Trail and Black Bridge Trail . With more than 41 trails covering 672 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.
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!
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?
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
About a 45 minute ride on the Erie Canal path ,starting at the Medina lift bridge, through farmland and villages (Middleport, Gasport) herons that are absolutely not afraid of you! Beautiful in the fall!
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....
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.
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.
Asphalt smooth and trail is terrific. Easy, flat trail with some water views passing Silver Lake/Pittsfield.
A nice 5 miles to a huge wash out shutting down the trail. We bypassed the closure using the road for 1/2 mi. Only to find another sign saying trail closed. Turned around , do not plan on going more than 5 mi from Keene! Frankie
Wonderful! the section north of Keene is just great. I admit there are a very few spots that are a little rough or a little wet but for 99% of it, anyone with even limited experience will enjoy it. I would not recommend this trail for a road bike although there are sections that are smooth enough for one. The only part that was a little concerning was near the landfill just north of Keene but that was only 2 tenths of a mile long and if concerned, you could easily walk your bike through that area. But honestly, the entire trail was great with several spots offering spectacular views. The surface is mixed depending on the area, some areas had grass while others were course sand. There were a couple rocky areas but those spots are few and very short.
Nice trail through the woods that opens up at the end at the boat launch for the Harriman Reservoir. Definitely not .5 miles; more like 3 miles out and back.
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