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 669 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

Ware to Gilbertville and Gilbertville to Wheelwright

November, 2024 by arno911

Rode the two sections of this beautiful trail today. From the parking spot in the middle of the Ware trail towards Gilbertville is a nice ride along the river. But a short one. Opposite the old factory the trail suddenly ends and there are handwritten signs "Stop, Don´t go further, Private property..." It would only take a few yards to reach the next road to travel on towards Gilbertville. No chance. Shame on you, property owners! (The trailmap shows a way through, but that might be an error?)

Okay, same way back and on to Route 32 past Gilbertville, where the next trailhead is waiting;-)
Smooth surface, well maintained and even good for kids bikes and flat all the way to Wheelwright. 3 nice old bridges. This is one is fully recommended! Absolutely worth it.

Ashuwillticook Rail Trail

Mid-Fall Ride

October, 2024 by willipar

Rode the full trail on a glorious October Saturday. the views were spectacular, peppered with fiery fall leaves. The trail is in incredibly good condition over the whole length. Such a lovely ride.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

hazardous obstacle course

October, 2024 by bikerdoc

My wife and I are both injured(fortunately not serious) after both of us thrown off our bikes simultaneously on a small poorly surfaced wooden bridge just north of Keene NH. The wooden boards were uneven and some rotted causing our bikes to wedge in a step-off causing us both to fall off our bikes. The trail had several road crossings just outside of the town of Keene which are very dangerous. There are tiny stop sign markings on the trail and no large or blinking light warnings on the crossing roads which have poor visibility in both directions due to curving of the road. I would not recommend this trail for transient travelers trying a new RT on vacation. This is for locals only who know the trail well in my opinion.

Accordion

Canalside Rail Trail

Trail Closed

October, 2024 by joerone_tl

Part of this trail is closed, my wife and I got about 2 miles or so in and there was a detour sign for the trail and we could not find where it picked up again. Road on the streets for a bit and then headed back to the truck, got about 5 miles in on the ride so not a total loss

Fort Hill Recreational Rail Trail

great trail

September, 2024 by leslie.sherman316

We did this trail today. It is quite bumpy but the scenery more than makes up for that. It goes through beautiful forests with frequent views of the Connecticut River. Don’t pass it up if you are in the area.

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.

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.

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.