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 437 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.
This portion of the Cheshire rail trail has almost no incline is completely straight and runs past a former major manufacturing complex, which is now vacant. Other sites include Keene police department and Keene ice and American house.
Start at the Peterborough Shopping Plaza parking lot. Stop in the Information Center across the street. It's operated by very nice local volunteers. Make your way north though the center of Peterborough. The surfaces are mostly paved & packed. You don't hit dirt & gravel until the upper half of the trail. Most riders stop at the school bus parking lot on Rt.202. There's a small parking lot there. If you cross the road you can pick up the Powder Mill Pond Rail trail and follow it northeast for another mile or so until it ends at Forest Rd. The trail gets rougher the further north you go but it's VERY manageable for most riders.
I've walked and biked this trail many times. Quite scenic in spots where it follows the Winnipesauke River but less so as it passes by backyards. Its a great way to get through the Tilton-Franklin area without having to ride the commercial strip on Route 3. There are attractions at either end, food mostly including a brewery, that offer a fun reward. Can also be combined with the Norther Rail Trail with a short road ride.
I've ridden this trail many times and it never disappoints. I have ridden all of it in sections and each one has it's own charm. In the Grafton-Canaan stretch it can feel remote even though the highway is nearby. The section from Boscawen to Andover always has folks on it though I have never found it too busy to enjoy. The save can be said for Lebanon out towards Canaan. There are services available along the way though it might require some road riding to access some of them. The Friends of the Northern Rail Trail group does a great job, is responsive to user comments and is working to address issues like toilet access. That being said there are long stretches where you have to be willing to use the bushes. It's absolutely a carry-in/carry-out situation so its a good idea to be prepared.
I do not recommend this trail. We have biked this trail a few times in the past, but we biked it on May 2, 2025 and found that is has gone downhill. We started at the Tilton end and had issues right away. First McDonalds and the motel at the start point have posted customer only parking signs (not sure if that is enforced). Going through Tilton business area was not good as we had to walk the bikes on the sidewalk since there is no bike lane and not safe to ride in the street. We had to ask where the trail was as we didn't remember as it had been a few years. Luckily once we got on the trail we remembered the rest of the turns as there are NO signs. The trail is very rough and only about 1/8 mile is paved at the Franklin end. There were also some questionable characters along the way and what looked like a homeless camp at the Franklin end. As one review stated, this trail needs policing. It is too bad because there is interesting history on the trail and nice views of the river.
I did this as an extension of a ride down from Newport on the Sugar River Trail. I agree with the comment above about the section along Washington street by all the box stores where you are essentially riding on the verge of the highway. It doesn't seem like it would take much to fix that section up and make for a more seamless connection to the Sugar river trail. It would also be nice at the end of the trail in Claremont to give some indications to local services (food!).
Last ride of 2024 and was it super! I have a gravel bike so no real issues with the multi-use aspect of the trail as it was in pretty good shape though you could expect to have a difficult time with skinny tires or after a prolonged dry spell. Very scenic, perhaps the most scenic trail I have ridden on in NH. I tacked on the portion into Claremont to get in the mileage and the part that closely parallels the highway is a bit sketchy.
The trail is much better than described, so it has had an upgrade. The trail is a uniform experience from one end to the other. The trail is gravel / dirt with no roots or rocks. It is slightly narrower than some other trails, giving you the feeling you were deeper in the woods. Most of the trail runs along the Piscataquog River and on the other side of the river is Rt 13 (some road noise). The northern trailhead gets close to the Goffstown Rail Trail and at the trailhead you will find road directions (about 2-miles) to get to that awesome trail.
The Common Pathway is also called the Peterborough RT. This RT adjoins the Old Railroad Trail and is about 5 miles north of Monadnock RT (we did all 3 trails the same day). The trail is mostly crushed stone but some asphalt as well as road ride. Some rough spots but no issue. Started at Trailhead for Old Railroad Trail and headed toward Peterborough. It is a nice town with several good eating and drinking places. Good trail and the Contoocook River runs along most of the trail. We did not do the trail south of Peterborough as it went from town, along 202 (traffic at 50+ mph) and was not reviewed as being an interesting ride.
e-Bike with 2" tires. The trail adjoins Peterborough (Common Path) RT. Rough trail with roots and rocks, so speeds above 10 are impossible to maintain. On a positive note, you really feel like you are in the woods. We were able to go slightly longer than the miles posted. A tiring short ride, but doable. Wife hated it, as too bumpy. Recommendation: ride Peterborough (Common Path) first as it is much easier.
Biked with e-bikes 2" tires. From the north going south (American Legion Baseball Field). Mostly crushed stone trail. Feels like a rail trail - level and wide. Only one rough area (RR ties and rocks for about 10 yds). The water on the left of the trail looked like it was drying up (no smell) and there was at least one nice lake (average views). Part of the trail runs along the highway. Only rode 5 miles as we didn't go much south of 202 (exceedingly difficult crossing at rush hour - be careful). Some of the reviews of the area south of where we rode indicate more difficult terain.
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