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 287 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)

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

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.

Battell Woods Trail

mountain Bike trail

July, 2023 by shelliott50

This is not your typical rail trail but a hilly narrow mountain bike trail. Lots of roots, ruts and mosquitos

Cheshire Rail Trail (Cheshire Branch Rail Trail)

Dangerous Spots

June, 2023 by flipandjo

We biked this trail from the Troy NH train depot north. My husband has a gravel bike and I have a hybrid. We are experienced cyclists. From Troy north to Keene the trail is very rocky and has not been maintained at all we would say. The Stone Arch Bridge that is often proposed to be quite beautiful has TWO OPEN manholes! No covers at all and one of them drops to about 8 feet deep. These are not noticeable until you are right on top of them. The deepest one at some point had an orange cone to mark it, but that has been pushed/fallen in.From the southern parts of Keene to the northern parts the trail is very nice, gravel, paved, well marked. North of Keene the trail is overgrown only 2" wide and at points under water. Signage was found fallen and on the ground, trail map holders were empty and untended. We do not recommend this trail.

West River Trail

trees down

June, 2023 by mitchkahl

Many trees were obstructing the trail making the ride from the trail head in South Londonderry to the campground difficult. Bring a Mtn bike or your regret using a street bike

Cheshire Rail Trail (Cheshire Branch Rail Trail)


June, 2023 by gcroteau1974

This is a great trail that I’m on most days.

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