Looking for the best trails around Windsor?

Explore the best rated trails in Windsor, 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 41 trails covering 419 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

Stevens Rail Trail

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

October, 2023 by imaginetravelsgd

This was a great ride in both directions. After talking with Tim at the Warner Fall Foliage Festival we found out they were adding more trail on the other side of the bridge starting next week.

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....

Accordion

Ammonoosuc Rail Trail

Poor condition

September, 2023 by joanhartzler

This trail is not suitable for biking at all. There are very large rocks and in places they dumped sand on the trail. Only rode from Littleton to Lisbon because the riding was so rough. We have hybrid bikes with suspension but we felt like it was way too rough! Never again! Get rid of the ATVs that tear up the trail or market this only to them! ¿

Ashuelot Recreational Rail Trail

Still a lovely ride in spite of washouts

September, 2023 by nanlovell77

I would hate for people to avoid this lovely trail because of reports of the washouts. By using the trail map from this app or even Google maps you can easily find nearby roads that allow you to ride around the closed sections. We had a lovely 18.7 mi ride today and we’re able to keep cool because of lots of shade even though it got up to 90 degrees! They were repairing the bridge on the road to the Slate Covered Bridge, but they paused work to let us cross. It will be repaired very soon.

Monadnock Recreational Rail Trail

Pleasantly Surprised

September, 2023 by fyredown

Truly a nice ride this weekend. Packed surface, mixed terrain but nothing our Surly Ogre's couldn't handle. This was not a crowded trail but there were a spattering of walkers, bikers, dog walkers. Made you feel happy to be alive! Whoever is maintaining this trail - thank you!

Hillsborough Recreational Rail Trail

Bennington to Deering - compared with Jaffrey to Rindge

September, 2023 by fyredown

What will it take to get the Bennington to Deering Rail Trail suitable for bicycle??? It is a very difficult ride with even fat-tired riders because of the loose terrain. And then if you try to avoid it by riding the road, that is almost impossible also due to all the pitfalls and holes. This could be such an attraction.

I tried the Jaffrey to Rindge trail this weekend and there was NO COMPARISON! Fun, enjoyable ride while this one remains disappointing.

Please put this one on your list to help!!!

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.

New Boston Rail Trail

perfect for walkers and bikers

September, 2023 by slasalle76

The trail guide book lists this as a 2-3 roughness, but I would keep it at 2. It's hard packed dirt or crushed gravel the whole length, and while I walked it due to the guide book description which said that half of it was really for walkers/hikers only, I competely disagree. If you want to ride, feel free to, as it's in great shape for all manner of bikes except a strictly road bike, as I assume road bikers want asphalt to ride on. I'll go back and do it again on my hybrid. I parked at Gregg Mills Rd, plenty of spaces, and there is parking for at least a few cars at all other intersections as well. Benches all along the way as well, so bring a picnic.

Monadnock Recreational Rail Trail

not great conditions

September, 2023 by emilyahagan

A mix of sand, packed gravel and flooded trail. Rather challenging terrain that required skilled navigating the trail . It was in horrible condition. The brewery in winchendon was wonderful, but you need to bushwhack through the trail and into an abandoned factory’s parking lot.

Monadnock Recreational Rail Trail

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer day

September, 2023 by bplatt1

Nice trail, kept in good condition. Tree lined with lots of shade perfect for a summer 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.

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