Windsor Trail is a 5.3 mile moderately trafficked out and back trail located near Windsor, Vermont that features a waterfall and is rated as difficult. The trail offers a number of activity options and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

Length5.3 miElevation gain2,500 ftRoute typeOut & back
Dogs on leashCross-country skiingHikingNature tripsSkiingSnowshoeingBird watchingRunningForestRiverViewsWaterfallWildflowersWildlifeBlowdownBugsRockySnow
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Reviews (195)
Photos (182)
Activities (167)
Completed (367)
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Kristin Khederian
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HikingClosed

Trail is CLOSED due to mud along with all other trails up Ascutney. Signage said these closures could extend through Memorial Day. Don’t recommend making the trek out to Ascutney until the early summer.

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Cj Bocklet
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Hiking

Trail head might be tricky to find but follow field behind Windsor Trail sign (pictured). Otherwise well maintained and marked. Great view from lookout. Leaves were tough on the way down. Bring your spikes. Needed for last third of trail.

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Matthew Remington
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Hiking

This trail was poorly marked. I read other reviews, and I am not sure what other people were talking about. I am fairly new at hiking, so I may have missed something. From the time I hiked up, and the time I walked down was a nightmare. I would recommend going with someone who is familiar with this trail.

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Rebecca Francoeur
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HikingGreat!

Beautiful trail! Snow is starting to melt, so be ready to sink, other then that we had our spikes and trudged our way up! Views are worth every step.

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Brian McInerney
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HikingGreat!

Awesome as usual; March 7 was easy crampon day and left snowshoes in pack. 2.5 hrs up and down; beautiful day and home by noon.

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Allison Brown
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HikingIcySnow

Holy thigh buster, Batman! Bring spikes, bring snowshoes. I used spikes on the way up and snowshoes on most of the way down. It’s steep from start to finish. Not much in the way of views right now. I made it to the shelter and went back. Not sure if the look out tower is open this time of year. Trails were sloppy, crusty and watch out for the post holing. A decent workout. Oh also a sh*t ton of what looked like coyote scat!

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Brandi Beebop
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HikingSnow

I really should have worn my snowshoes. The trail was lightly packed so I moved like a speedy snail, sinking into the snow. A very well marked trail with amazing views at the top.

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Marisa Patelli
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Hiking

Very snowy conditions but absolutely beautiful!

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Megan G
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HikingGreat!

snowy and beautiful, great in yaktrax or microspikes. took us about 4 hours with plenty of time to enjoy the view at the top

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Zander B
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Hiking

Great hike. Almost all uphill on way up. Awesome views at summit and well marked. Cramp ons needed in winter. Recording restarted and missed first 30 min or so.

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Cj Bocklet
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Hiking

Crisp sunny day in the teens lite breeze. Well marked. Steady rise from parking to summit but there was no cursing! 360 view from lookout tower was fantastic

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Michael Storey
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Hiking

Very snowy & slick

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Katie Cole
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Hiking
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Jake Huckins
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Hiking
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Beth Piro
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Hiking

Slippery and muddy

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Joseph Centeno
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HikingGreat!

Pretty difficult hike due to the constant incline. Until you reach the top there is hardly a flat moment. The trail is as well marked as possible. Any confusing moment or point where it seems the trail diverges there are obvious trail markers and at every junction/intersection with other trails there are marked, wooden, signs that point the right way. I really enjoyed the changing of the foliage from the base to the peak, meaning that the types of trees and kind of vegetation surrounding the trail slowly changed based on the altitude of the hike. In addition to the peak I went to Blood Rock on the way up and the way down as well as Brownstone Rock. In total I took a little over 2.5 hours with a those added stops. I was moving pretty fast on the way down, though, so I'd say 3 hours or so is a good benchmark.

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Adelle Condon
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HikingGreat!

Challenging hike, very steep, great workout. We were unfortunate that it was cloudy at the top so we didn't get to see the views of the fall foliage. We completed the hike in 2H45M moving at a steady pace on the way up, our trip down was a little slower trying to safely pick our way between rocks and roots in some areas. Looking forward to doing this hike again in better weather to get to see the views.

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samuel wood
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Hiking
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Conan Deady
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HikingGreat!Rocky

We really enjoyed this trail. When you gain 2500 feet in 2.7 miles you know you are working. The grade is moderately steep from start to finish. Trail starts out wide and smooth but is generally pretty rocky and covered with roots. This adds a little challenge but is pretty manageable. I think this is a good hike for fit people who enjoy strenuous hikes but not so much for casual or ambivalent hikers. Views from the top are pretty good, especially if you climb the observation tower. Also the lookout just off the trail at Brownsville Rock is definitely worth the very short detour.

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Kara Macdonald
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Hiking

Most of the hike is a pretty basic in the woods trail hike, not the most challenging or exciting but nice and easy to follow signs/ trails. Took the detours to Blood rock, Cascade, and Brownsville Rock. Those were nice little private spots to stop for some good and enjoy the views.

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Joshua Conover
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Hiking

A nice moderate climb, with several good lookout points and a large summit area to explore!

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Damon Kindopp
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Hiking

Great view & was a nice challenge !

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Jason Bouffard
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Hiking

Pretty steep for the majority of the trail. Great workout!

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Theresa Marie
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Hiking

Beautiful conditions, tons of people at the top

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Regina Chang
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HikingGreat!Rocky

Great trail. Well marked (you have to pay attention where you are going of course!) Make sure you stop by Brownsville Rock which offers the best view before heading to the observation tower!

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Britt J
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HikingGreat!

If you follow the markers and your name isn’t Kai, this is a tough but rewarding roughly 3 mile hike (one way).

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Noel D
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HikingGreat!

Found it very similar to Brownsville trail. Very enjoyable looking forward to doing it again.

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