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 Cross Vermont Trail and South Barre Bike Path . With more than 22 trails covering 286 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

Northern Rail Trail

great trail

August, 2024 by mflayhan

One of the best biking trails smooth great steady cruiser trail loved it

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.

Northern Rail Trail

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

June, 2024 by klracicot

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

Accordion

Sugar River Trail

amazing Trail

April, 2024 by nariipr

We had a great time on this trail, which was easy to navigate. It was our first outing this season since we acquired an ATV for my wife and we enjoyed spending time together while exploring nature. We encountered people walking their dogs and bikers along the way. The trail was well-maintained and clean. We made sure to slow down and say hello to everyone we met. We will definitely be back on this trail again!

Cheshire Rail Trail (Cheshire Branch Rail Trail)

We found the Trail notTrail not as described

October, 2023 by luvaneezer

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

Delaware and Hudson Rail-Trail

dog warning

September, 2023 by guamlee7

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....

Northern Rail Trail

Danbury Country Store to Tewksbury Pond, Grafton

September, 2023 by chriscarney

Parked across from the Danbury County Store. Headed west towards Grafton. Only saw a coupe peopling using the trail this late Friday afternoon. Trail was smooth and dry even with rain the prior day.

Sugar River Trail

Sugar River

September, 2023 by neerod11

September 2,2023. Trail is in sad shape in some areas. Sandy and rough. My fat tire bike handled it well but I can see where it could be issue for skinny tires. The scenery outweighs the bad trail. Most problem areas are caused by ATV’s and dirt bikes. Everyone on the trail is courteous and that helps.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Great trail even after a bad weather summer

August, 2023 by twelch11

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.

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Good trail in a challenging year

July, 2023 by twelch11

Went from the southern end at State Line Circle to Rockwood pond. Once you go past the Fitzwilliam Fire Department/Fitzwilliam Station it starts to get a little rough through and past Royalston Road and Richmond Road with steep hills at each road crossing and pretty much unmaintained trail. Then it smooths out up to Rockwood Pond. Rockwood pond is a very nice stretch with great views of Monadnock to the east. Great trail that needs a little work. Very manageable with a mountain/fat tire bike. Wouldn't try it with a street bike. Most enjoyable trail.

West River Trail (Windham County)

Trail is well maintained, and an easy ride. We started out at the south end by the Marina. A couple of beautiful waterfalls along the way.

July, 2023 by bplatt1

Trail is well maintained, and an easy ride. We started out at the south end by the Marina. A couple of beautiful waterfalls along the way.

Valley Trail

Absolutely not a rail trail at all

July, 2023 by mjfish

This trail starts as double track, then is closed due to mud, and washouts. Several single track trails off Valley Trail. “Maid Marion” takes you to Mt Snow.

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