Looking for the best trails around Rutland?

Explore the best rated trails in Rutland, VT. Whether you're looking for an easy walking trail or a bike trail like the South Barre Bike Path and Sugar River Trail. With more than 20 trails covering 196 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

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Cheshire Rail Trail (South Portion)

October, 2022 by gail glines

I rode from near the Massachusetts state line and Rt. 12 north to Keene, NH on 10/01/2022 using a cyclocross bike with mid-width knobby trail-riding tires. The conditions were very good in general but, in the portion where it reduces to a single track in width you often needed to dodge rocks sticking up in the path. The portion of this trail with several deep cuts through the rock hills are quite a memorable sight to see. Take care crossing the stone arch bridge because there are no guardrails. Overall this was an enjoyable trail to ride.

Valley Trail

great quiet walk

September, 2022 by dclippa

This is a lovely, easy , quiet walk. Much improved from a few years ago, based on the reviews. Great for families, dogs and their humans.

Delaware and Hudson Rail-Trail

The VT portions are great, NY not so much

August, 2022 by keith.mitz

I rode the whole trail out and back in August 2022. You really need tires with some knobs for this trail. I used a gravel bike with small knobby tires. It's not hilly or technical, just rough in places. VT uses 3/4" gravel which would make it difficult for standard road tires.

The VT portions of the trail are well maintained and have great signage, historical and otherwise.

The NY section is not as well maintained, specifically, the portion from the state line south of Poultney to Middle Granville. Google Maps displays the rideable portions, although once you cross the state line southbound, the trail gets quite narrow - tick spray recommended. There is a spot where you have to carry your bike over a pile of slate. It leads to a farm road, red in color, and leading to a red barn on route 22A. Not sure that is legit. There were no signs saying not to.

I rode south on 22A to Butler Road, then right on Depot. The trail starts again just after the cemetery. You have to maneuver around an active dairy farm to get back on the trail. Wasn't pretty but it works. Once you get south of the dairy farm, it's fine. Going through Granville proper is also confusing. Again, Google Maps is your friend.

I recommend Sherman's Store in West Rupert, near the trail end, for sandwiches and energy drinks. You can get there from the trail via Mill Road. Look for a business called Authentic Designs for the turn.

Accordion

Warren County Bikeway

Summer Ride

July, 2022 by flthea

Absolutely beautiful asphalt trail mostly covered by canopy of trees, temp 10*cooler than in the sun. Here the end of July. Parked in the Million Dollar beach parking lot $10 and a great place to leave the car for the day¿¿rode around town, enjoying the lake and lunch afterward.

Northern Rail Trail

Great Trail

July, 2022 by trzpna8zd9

Fifty nine mile long well maintained trail that provides a nice mix of scenery the entire length.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Keene to Troy and back

July, 2022 by slasalle76

I recently rode my hybrid from the Stone Arch Bridge to the Troy Depot and back, and found the trail to be in reasonably good shape along that stretch. I parked right on 101 in the open turn off and my car was undisturbed for the couple hours I was out. The trail southbound is the slight incline, as I was going a few mph faster on the way back. The trail does narrow down to a single track in the middle of that stretch as I feel it does not get enough use to keep the weeds at bay, and a few fallen trees meant stopping to lift the bike over. Overall, quite pleasant, and Troy is a lovely little town.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Nice, shady, secluded trail

July, 2022 by gpiatetsky1

We parked in Keen at the Cheshire Trail Parking spot and went north to Walpole. Nice trail, unpaved but well-packed earth and shade. We have 2 electric bikes, so 2 steep inclines were not a problem. Unfortunately, after about 10 minutes we run into a closed section. Not sure when it will reopen - we saw no signs of work. We turned and went south to Keene, and in the center of Keene we followed signs for a bike trail which led us to Ashuelot River trail. It has several pretty bridges over roads, about a mile of paved section, and once it leaves Keene it is unpaved, but still has good surface and shade.
In Keene you can also go to southern section of Cheshire rail trail, but it is not easy to find, so use Google Maps on your phone to be sure.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

If you want to avoid the crowd and see the landscape

July, 2022 by ttilson19

Parked at the old train depot in Troy and rode South to the end at the Mass border and back. The trail is not paved, not groomed but that’s part of what makes it fun. Riding through the woods, along a stream, crossing a wetlands with high bush blueberry bushes loaded with fruit and on the way back jumping in a clear water pond to cool off, with a view of Monadnock …perfect day! Oh, and we saw one runner and two people picking those berries…a very memorable and delightful day on the trail.

Delaware and Hudson Rail-Trail

Castleton to Poultney fun ride

June, 2022 by vtpredom

We were pleasantly surprised with how nice this trail is based on some of the reviews. We ride hybrid bikes with shocks and comfort seats and are accustomed to riding gravel and backroads so this trail was just what we look for. Trail is firm packed gravel and very smooth, no potholes or washboard experienced on our ride. Plenty of parking available on the Castleton end of the trail, we parked in the trailhead lot across from the Amtrak station. Definitely in our top 10 list of VT rides.

Delaware and Hudson Rail-Trail

Carleton to Poultney section somewhat better but still rough due to horse traffic.

June, 2022 by rbjpye

Carleton to Poultney section somewhat better but still rough due to horse traffic.

Montpelier Recreation Path (Winooski Path)

pleasant unexpected ride

June, 2022 by richmedcraft

I was traveling through Montpelier on Rt 2 along the river after being unable to find another trail several miles away. I saw signs for the Cross Vermont Trail and saw what looked like a trail across the river. I kept a lookout for other signs and followed one to a dirt road that extended along the north bank of the river. I parked there and rode my bike along what is apparently an extension of the Montpelier Recreation Path that is not described yet in Trail Link. The surface is crushed stone for the most part and I followed it until it ended in a narrow dirt path blocked by a large piece of old equipment. I then backtracked and followed the trail into Montpelier where it became paved and passed across streets and railroad tracks. I turned around in the downtown and rode back to the car for a total of about 7 miles. It was a pleasant ride and the scenery outside of the city was nice.

Northern Rail Trail

Nice ride

May, 2022 by ashbaugh4220

Wife and I started in Hanover and went 15 miles the turned around and came back. Beautiful streams and lake on the way. Trail wasn’t crowded on this Thursday.

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

Your account has been deleted.