Looking for the best trails around Bennington?

Explore the best rated trails in Bennington, VT, whether you're looking for an easy walking trail or a bike trail like the Spring Run Trail and Appel Way Trail . With more than 41 trails covering 662 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

Mass Central Rail Trail

Weston-Waltham section

September, 2024 by msandman1943_tl

This section (8/2024) is about 5 miles long. It goes through woodland and past leafy backyards, but it runs alongside the towers for a high-tension power line. Trees have been clear-cut about 25 feet on both sides of the trail, so there's no shade along this section. But the trail is wide, very straight, and smoothly paved. It has a few small ups and downs and crosses four or five quiet roads before it comes to a traffic signal at the intersection of Routes 126 and 27. Just beyond, the trail turns to crushed stone with a few sandy patches. There's a large supermarket and shopping center adjacent to the trail at that point.

Ashuwillticook Rail Trail

Late summer ride

August, 2024 by mgraska54

Beautiful smooth ride. Recommend for anyone seeking a pleasurable experience.

Ashuwillticook Rail Trail

A top 5 New England trail

August, 2024 by andrix

Lots of wildlife along this pristine trail with plenty for bathroom facilities and benches to take a break. Trail is maybe 70% shaded which kept the temperatures down but still glad we had our suntan lotion. The trail passes a large lake and goes through plenty of wetlands giving lots of interesting views. Road crossings were well marked and safe. Our stay at the Williams Inn in Williamstown was definitely a cut above the norm and from there was maybe a 15 minute drive to the trailhead.

Accordion

Albany-Hudson Electric Trail

Nassau to Stuyvesant Falls Park

August, 2024 by andrix

This trail (14 mile section) was in pristine condition with surprising amount of wildlife (herons, deer, turtles) along the way. Park, falls and 1800's mill factory at the southern end was worth a stop. Maybe shaded 50% so suntan lotion a must. There's a parking lot in Nassau right next to the trail. As others have mentioned, very few bathroom facilities on route.

Albany-Hudson Electric Trail

One of my favorites along the EST

July, 2024 by robert.richter89

I've been riding many of the trails that make up the Empire State Trail system though out the years and the Albany-Hudson Electric Trail is one of the best in my experience.

I parked at the Stuyvesant Falls Trailhead and headed towards the Miller Road trailhead right outside of East Greenbush making for a 42 mile round trip. There are a fair amount of road crossings on this trail but all of the busier ones have crossing lights and I found that motorists were very courteous to me at every one. There is also a few short on road sections on quiet streets that are all very well marked. I was able to keep on the trail without too much confusion.

The trail is a mix of asphalt and tightly packed gravel and is in very good condition. My only complaints are a lack of benches and bathrooms directly on the trail. The trail is also not the most shaded so be mindful of that on a hot summer day. The towns along the trail all offered places to eat and resupply so that's always and option.

Erie Canalway Trail

The trail is well marked it's a bit tough going on roads through parts of Lockport. Once back on the trail, is well maintained.

July, 2024 by auntgnu

The trail is well marked it's a bit tough going on roads through parts of Lockport. Once back on the trail, is well maintained.

Delaware and Hudson Rail-Trail

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

June, 2024 by mdnkcn

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

Mass Central Rail Trail

MCTR - West Boylston to Rutland

June, 2024 by closey2112

Ok, I recently purchased a ‘24 Trek Checkpoint ALR 5 axs gravel bike. This section of trail is absolutely amazing. Roughly 26.3 miles round trip from West Boylston to Rutland. Starting in West Boylston, Ma you head west. The trail is hard packed dirt. Smoother than most roads in Mass! ¿ No, seriously! Just be careful, this section up to the I-190 bridges, there’s usually a lot of traffic. Especially people with doggos. Some more cognizant than others. But once you cross under the bridges, no dogs are allowed and the traffic thins out. The best section is at the parking lot on Mill St - Holden. It’s packed gravel and as wide a road. It meanders up to the mail Trail and is packed gravel all the way until you hit construction on the trail. So much fun!!!

Erie Canalway Trail

Camillus to Syracuse with side trip on Onondaga Lake Trails

June, 2024 by wrogers1

In early June, we rode the section of the Erie Canal from Camillus to Syracuse. We also took a side trip on the Onondaga Lake West and East Shore Trails. Round trip, we biked approximatel 30 miles.

We parked at the June Reed Webster Park. The bathrooms were open. With that said, we have been there before and they have been closed. I would not count on them 100%.

The trail was in excellent shape. The Erie Canal section was hard a packed with small gravel. We did encounter hills, which we did not expect on a canal trail. They were small and manageable. Most of the hilly sections were paved, making them easy to navigate. The Onondaga Lake trails are paved and in fantastic condition. We only came across two small sections with tree root bumps.

This section of the Erie Canal Trail goes through the New York State Fairgrounds. It was eerie and strange to be at the Fair when no one else was around. Made for a unique experience.

The Onondaga Lake Trails were a pleasure with views of the lake, woodlands, birds, and flowers. We saw several bluebirds, which is not something we encounter routinely.

The Onondaga Lake Trails are part of the Onondaga Lake Park which has multiple bathroom facilities and picnic tables. We ate our lunch with a view of the lake and pickleball courts. There were a people playing, which provided our lunch time entertainment.

The only potential downside is the trail near Camillus is next to a garbage dumb. It is landscaped nicely with wild flowers in abundance and we did find a turtle on the path. We noticed an odor on our way back when the temperature was hotter. On the positive side, it is a productive use of the land.

We give this trail a thumbs up and will ride it again.

Ashuwillticook Rail Trail

Nice weather makes the ride nice

June, 2024 by vc2019

Started in Adams and rode to the end and back. Nice weather on this wide paved and shaded trail. It is in great condition. There are a number of road crossings but most are small streets. The gates are all the same, an opening on each side and we saw atleast two recumbent trikes make it through without problems. Photo to show the gates today.

Ashuwillticook Rail Trail

A must ride

June, 2024 by ahanks

Visiting in lower NY area and had this on my bucket list. It was a well paved and maintained trail. Parked at railroad at in Cheshire and rode to the parking area in Pittsfield and then back and a few miles into the Adams area. All in 18 miles. Plenty of options for parking, bathroom Facilities in a few areas and many benches and picnic tables placed to stop and take a break or enjoy the views of the Lindai a or chechsire reservoir. It was well worth the trip!

Rocky Hill Trail

Completely paved; easy

June, 2024 by pianoemily

This was a very short trail which was completely paved. It was nice and shaded due to the trees. It would be an easy walk with grandparents (there are benches) or young children. I recommend setting your gps to find something like 134 Sandy Hill Road in Florence. From there, you can easily find the trail beginning. To get my 10,000 steps I had to go back and forth on the trail a lot. But I still appreciated it fully paved! Seems like more of a neighborhood morning walk trail.

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