Overlook Mountain Trail

MODERATE 188 reviews
#1 of 53 trails in

Overlook Mountain Trail is a 4.8 mile heavily trafficked out and back trail located near Woodstock, New York that features beautiful wild flowers and is rated as moderate. 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.

4.8 miles 1407 feet Out & Back

dogs on leash

birding

hiking

nature trips

snowshoeing

walking

views

wild flowers

wildlife

hiking
18 days ago

18 days ago

hiking
18 days ago

hiking
27 days ago

29 days ago

1 month ago

hiking
1 month ago

hiking
1 month ago

Loved this trail in winter- great mountain and valley views as you climb and panorama of Hudson River valley and lots of surrounding area from the fire tower at the top. In summer I find this trail's scenery not worth the effort- but without all the greenery on the trees it is really incredible in winter! Quite busy- lots of hikers on this January wknd!

hiking
1 month ago

hiking
1 month ago

Somewhat boring as far as 'hiking' trails go, but a good walk up. If you go at a good pace, you can get the heart going. There is an awesome view at the fire tower up top though.

2 months ago

Pretty easy walk up . Beautiful views at the top and what a day blue skies plenty of sun and cool and crisp .

hiking
2 months ago

this was a great hike! I'm unsure why people said it was boring. there were great views and interesting things the whole way up the trail. the scenic overlook was amazing as well as the firetower and the ruins were a great bonus. easy trail! please follow the leave no trace policy, so much trash and dog poop. really not that hard to walk your dog away from the trail. other than that conditions were a bit icy, needed spikes. definitely returning in the summer.

hiking
2 months ago

Easy walk up. Trail itself is somewhat boring until you get to the hotel, fire tower and lookout point. They are the prime reason I gave it a 3.

3 months ago

3 months ago

3 months ago

3 months ago

Pretty straight up for a long while — but great views along the way, and beautiful summit.

hiking
4 months ago

Great views of the Catskills both from the scenic overlooks and the tower itself. If you're a frequent hiker or are doing this as part of the fire tower challenge I would recommend going during the winter as parking is limited and this is a VERY popular hike.

hiking
4 months ago

This, so far, is my favorite hike in New York. The hike wasn't very difficult at all and there was so much to see and do. First there's the abandoned hotel to explore, then you can conquer the fire tower, and finish off with an amazing view. At first I was a little wary of the rattlesnake warnings but we didn't see one the whole time, so as long as you keep your eyes open for one I wouldn't worry about them.