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 432 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

Ammonoosuc Rail Trail

No Longer a trail for bicycles

October, 2024 by gjerstak

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.

WOW Trail

wow trail

September, 2024 by r1paull

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.

Fort Hill Recreational Rail Trail

great trail

September, 2024 by leslie.sherman316

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.

Accordion

Ammonoosuc Rail Trail

Trail is outstanding!

September, 2024 by ponttichuck

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!

Winnipesaukee River Trail

well maintained with beautiful views of the river

August, 2024 by brenda.viglienzoni

This trail was lovely. I did the entire trail both ways in a couple of hours. Mostly flat and well maintained. Began in Tilton on Rt 140 and road to the end in Franklin. Many nice places to stop along the way. Took some great pictures. It was a bit confusing when the trail ends and you are routed down Main Street in Tilton. I almost turned around at this point. Honestly It’s really not that far through town. Just be careful of cars backing out of parking spots. The vistas are worth it, keep going. Looking forward to checking out another trail.

Northern Rail Trail

great trail

August, 2024 by mflayhan

One of the best biking trails smooth great steady cruiser trail loved it

Concord-Lake Sunapee Rail Trail

so much to do

June, 2024 by carmen347

I have been waiting to try this route for several years. Always hearing that it wasn’t close to being finished. I was very disappointed to see firsthand that virtually nothing has been done for those years. The first mile from Concord is covered with packed cinder, but beyond that the trail is still raw and rough with exposed rocks and roots. Not sure why this project has stalled but I will not be riding it or supporting it until domething more is done to show progress. tiding it ir supporting it until I see something

Delaware and Hudson Rail-Trail

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

June, 2024 by mdnkcn

We biked the entire northern half of the D&H Rail Trail to the NY state line. Was pleasantly surprised to find no ruts. Trail was mostly made up of crushed stone. It's mostly a scenic ride, I would recommend this Rail Trail.

Northern Rail Trail

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

June, 2024 by klracicot

Rode from Lebanon to Grafton, beautiful trail, especially for a gravel bike. There some single track sections, but that added to experience. Loved the fact that it crossed the river many times thus many bridges and several tunnels.

Laverack Nature Trail at Hawkins Brook

An All Person Trail

June, 2024 by 7zvnmykbyx

This trail was designed with accessibility in mind. There is ample parking. Half the trail is in the sun and the rest is shaded. There is a combination of boardwalk and sustainable trail. People who use mobility devices - manual chairs, scooters, electric wheelchairs will find this a user friendly trail. It’s quiet, follows a brook, and is teeming with birds. There is also informational signs along the trail that describe the habitat. ,

WOW Trail

Ok Trail

May, 2024 by justin.c.perry84

This was an OK trail. We enjoyed that it was pretty well marked with the exception of one crossing near some train tracks. Too many road crossing points. Portions of the trail were rough because of roots growing under the pavement. We actually saw a runner take a pretty nasty spill because of the rough surface. It was nice to check it out, but we won’t go out of our way to come back.

Sugar River Trail

amazing Trail

April, 2024 by nariipr

We had a great time on this trail, which was easy to navigate. It was our first outing this season since we acquired an ATV for my wife and we enjoyed spending time together while exploring nature. We encountered people walking their dogs and bikers along the way. The trail was well-maintained and clean. We made sure to slow down and say hello to everyone we met. We will definitely be back on this trail again!

Find Nearby City trails

Register for free!

Register for free with TrailLink today!

We're a non-profit all about helping you enjoy the outdoors
  • View over 40,000 miles of trail maps
  • Share your trail photos
  • Save your own favorite trails
  • Learn about new trails near you
  • Leave reviews for trails
  • Add new and edit existing trails

Get the Free TrailLink App

The trail is always better with TrailLink

Scan the QR code to get TrailLink on your phone

Explore by City

Explore by City

Explore by Activity

Explore by Activity

Log in to your account to:

  • View trail paths on the map
  • Save trails to your account
  • Add trails, edit descriptions
  • Share photos
  • Add reviews

Log in with Google

Log in with Apple

OR

Register for free!

Join TrailLink (a non-profit) to view more than 40,000 miles of trail maps and more!

Register with Google

Register with Apple

OR

Your account has been deleted.