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.
Overview The Ammonoosuc Rail Trail carries its users for 23.46 miles along the scenic river that shares the trail's name. The river itself...
Appel Way Trail offers a paved route of about a mile through woodlands on the north end of Keene. Most notably, it offers a connection...
Closure Notice: Due to flooding, the Ashuelot Recreational Rail Trail is closed from Pine Street to Sawyer's Crossing Road in Swanzey.
In Woodsville the trail starts across from the Subway Restaurant across from the the Oceans Job Lot Store and next to the Woodsville...
The Bobby Woodman Rail Trail, a hard-packed dirt and gravel pathway, begins off a quiet street at the southern end of Claremont and quickly...
The Catamount Trail offers 300 miles of backcountry skiing stretching across Vermont, from the Readsboro on the Massachusetts border, to...
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Overview The Cheshire Rail Trail connects Fitzwilliam, Troy, Keene, Westmoreland and Walpole. The 42.4-mile trail has a mostly gravel and...
The Common Pathway travels 5.5 miles from the outskirts of Peterborough south to downtown’s Noone Falls area, paralleling US 202 and the...
Following the historic Concord-Claremont Railroad corridor, the Concord–Lake Sunapee Rail Trail will eventually connect communities from...
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 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.
My wife and I are both injured(fortunately not serious) after both of us thrown off our bikes simultaneously on a small poorly surfaced wooden bridge just north of Keene NH. The wooden boards were uneven and some rotted causing our bikes to wedge in a step-off causing us both to fall off our bikes. The trail had several road crossings just outside of the town of Keene which are very dangerous. There are tiny stop sign markings on the trail and no large or blinking light warnings on the crossing roads which have poor visibility in both directions due to curving of the road. I would not recommend this trail for transient travelers trying a new RT on vacation. This is for locals only who know the trail well in my opinion.
The scenery is very nice which is why I gave it more than one star. The surface is sand. Sometimes pretty well packed. Other times quite loose. It was doable with our hybrid bikes, but a lot of work and not much fun. Add to this a steady stream of dirt bikes and 4x4s kicking up dust and spewing fumes! Just not our kind of cycling.
We road 5 miles of the trail starting in Littleton.
But after 5 miles we turned back because ATV's have torn-up the trail.
This trail is OK for walking, but no longer OK for bicycles.
It is sad. It would be a nice trail if the ATV's had not destroyed it.
Sept 30th not a good trail ! We ran into several meth heads and police taking them into custody, Scarey stuff to say the least. We will not be back.
We did this trail today. It is quite bumpy but the scenery more than makes up for that. It goes through beautiful forests with frequent views of the Connecticut River. Don’t pass it up if you are in the area.
Whatever the previous people experienced has been taken care of … the only obstacles are the barriers you go around preventing atvs from using the trail … it’s not a paved trail but it is very smooth for a natural trail… its absolutely gorgeous from Littleton to the nh border… today I am biking with my sister and brother in law and look forward to exploring the wonders of nature and enjoying every minute of it!
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