Find the top rated walking trails in Windsor, whether you're looking for an easy short walking trail or a long walking trail, you'll find what you're looking for. Click on a walking trail below to find trail descriptions, trail maps, photos, and reviews.
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This Trail has been all redone we started at Ricker pond and went to Kettle pond was so much fun the views were amazing
Despite all the bad reviews for this trail we gave it a try and I'm so glad that we did. It was a little rough in some spots but nothing terrible. There are some scenic parts of the trail, a few trestle bridges, and one small tunnel. The river view is breathtaking in many spots. There's a great view where the river bends near a long covered bridge with a little chapel in the background...this time of the year the foliage just added to the beauty.
Short trail that is very much an extension of Sugar River trail, but without much scenery, other than the last .5 mile. The first portion of the trail that runs along the road is safe and wide, but its surface is a little soft. If you ride the Sugar River Trail, you should ride this trail as it is short, it adds to the exercise and the road portion is unique. I applaud and support all trail extensions.
This is one of the prettiest trails in the state. It runs along the Sugar River almost the entire ride and there are numerous bridges, including two covered rail bridges. I rode and e-bike with 2.1" tires. I agree with the other reviews concerning bikes, sandy but rideable. I left from Newport, and the sand was only an issue during the first 1.5 miles and then sporadically thereafter. I found the best way to deal with the back tire sliding out in the sand was to use higher levels of assist than I would normally have used. This trail can easily be top rated if it had a firmer surface. I passed 2-ATVs and 2-motorcycles and all four were exceptionally courteous. I did the Bobby Woodman trail too as part of my ride as the two trails are seamless.
Rode 2.5 miles from Wilmington north on mountain tire bikes and it is doable but rough with roots and rocks. Nice bridges but missing signage in some areas, others well marked. No washout areas close to Wilmington.
We rode the trail in early September on a Thursday and Friday. Thursday we started at Webster Lake and headed south (east?). Friday we rode from Webster Lake to the covered bridge. This second part of the trail was better riding than the other direction, which had more sand and was sometimes a slight bit challenging on our hybrid bikes (but maybe a better work out). We saw riders and walkers, but it was not crowded at all. Mostly we had this beautiful place to ourselves. We'll return for sure. (We camped at Granite State Campground about 30 min from where we began our rides.)
Really nice accessible trail for people of all abilities. Wheelchair friendly and just shy of all the requirements to be classified as a Universal Access Trail. Very well thought out trail, Bravo!!
We rode to the end of the trail, then continued on Rice Farm Rd. to the dangerous intersection. we missed the entrance to the trail on the way back, so got a good workout on some hilly spots on the road.
On the packed sand patches, keep an eye out for roots that can be a bit dicey. In some spots along the gravel sections, the gravel can be a bit loose, so pay attention to the trail.
Beautiful trail. Enjoyed the sites, sounds and smells. It runs along the river. I got on at the Depot Rd parking lot in Boscawen. Very easy access and plenty of parking. I Road 15 miles. The trail is fairly level with very little incline.
First time and loved it! I rode the entire route, starting at the south end parking lot. (42.758592, -72.471175) This trail has some unique features and the scenery is beautiful as you ride next to the river and through the woods. As a former rail, this trail has nice and gradual elevation changes and has fun bridges, which all seem to be maintained well.
At the time of my ride (end of Aug, '25) there were a couple of detours around mile 14 and 16 (heading north) but they have good (not great) detour signs listed to continue the route with a short road detour. As some folks mentioned, there are a few areas that look like they would be pretty wet during the wet season, but I had no issues with any area of the trail and never had to stop for downed trees in the way.
I rode my gravel setup (no suspension, 35mm tires) and had a blast! I'd highly recommend the trail and hope to be back for another spin soon.
We found this trail to be well maintained. Not as smooth as some rail trails, but smooth enough on our full suspension fat tire bikes. Hard tails may not enjoy as much. Nice scenery along the Connecticut river.
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