Overlook Mountain Trail

HARD 186 reviews
#1 of 53 trails in

Overlook Mountain Trail is a 4.6 mile heavily trafficked out and back trail located near Woodstock, New York that features beautiful wild flowers 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.

4.6 miles 1430 feet Out & Back

dogs on leash

birding

hiking

nature trips

snowshoeing

walking

views

wild flowers

wildlife

hiking
1 day ago

3 days ago

6 days ago

hiking
11 days ago

hiking
27 days 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.

1 month ago

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

hiking
1 month 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
1 month 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.

2 months ago

2 months ago

2 months ago

3 months ago

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

hiking
3 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
3 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.

Great spot
Trail has easy terrain to navigate but it's steep
And couldn't have asked for a more beautiful day

hiking
3 months ago

Really lucked out with the timing because downpoured right when we finished, which would make the hike really miserable. Took us 2.5 hours to go up and down with a 6 month old puppy. Going up was a real workout but doable at a fair pace. Those with bad knees should consider hiking sticks for going down. Constant steady incline up wide well defined trail of dirt and rocks. The abandoned hotel was a good challenge marker... right when you want to stop and take a break you see the hotel ruins, so it's a natural break place maybe 2/3 up the mountain. Then comes the tower. If you made it to the hotel, you might as well keep going to the overlook tower. It seems flimsy to look at, but when you start climbing and grip the metal rails you know that thing won't blow over. Worth the climb to go up that tower. Heart beating, thrilling height. Would do again! Saw someone running the trail... kudos to that runner!

hiking
3 months ago

Steep walk up with minimal views, but the eerie ruins and the scenic viewpoint at the top are a must-see. Top of fire tower closed for winter but you can climb 90% up. We loved it and so did our bulldog!