Explore the most popular trails near Windham with hand-curated trail maps and driving directions as well as detailed reviews and photos from hikers, campers and nature lovers like you.

Windham, New York Map
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Although I would classify this trail as an ankle and knee-buster, I wouldn’t call it as hard. As others have described, the ascent is very gradual. However, the majority of the trail is composed of exposed rocks and roots and this nearly burned my knees out. I have been hiking on 6-9 mile trails out west this summer and this one was by far the worst on my joints. If you like to hike with poles, I’d highly recommend bringing them! Mine saved me on the way down and helped me keep my balance throughout.

A steep and steady uphill climb. No tree cover so shade is minimal but that also affords a fairly continuous view of the surrounding mountains. The trail is wide and clear because it just follows a ski slope right up the mountain at the resort. The trail is rutted with a lot of gravel and large rocks mixed, making especially the downhill footing a little bit unsure. Easy to get to and worth doing once but I probably wouldn’t go back to it before exploring the rest of the trails in the area.

This is one of the easier 3500 mountains, so I'm not sure why it's rated 'hard'. In fact, this was the very first 3500 my wife and I attempted when we took up hiking . We're in our 50s and, at the time, were in pretty poor physical shape. Yes, there are some steep sections where you'll need to scramble and grab hold of trees or roots, but overall this is not a difficult hike. (Difficult or, more like it, exhausting would be the Table/Peekamoose mountains hike; we wobbled back to the car for the last mile or so that day.)

We hiked Windham on a cool October day and the foliage was just beautiful. There's no cannister on this hike. You'll find the summit fairly easily as it is right in the middle of the trail and you can practically trip over it. There are some nice views at the summit. Facing north, you'll be able to make out the Adirondacks on a clear day. Beware that the short steep sections may be too difficult for dogs to navigate without help.

Near the beginning of the hike is a set of new trails around some old cranberry bogs. Make sure you have the newest Catskill trail maps from the NY/NJ Trail Conference so you can take those as well if you want to lengthen the hike.

An average hike. Has a nice lookout BUT we saw lots of snakes!

trail running
1 month ago