Overlook Mountain Trail

HARD 124 reviews
#1 of 55 trails in

Overlook Mountain Trail is a 4.6 mile heavily trafficked out and back trail located near Woodstock, NY that features beautiful wild flowers and is rated as difficult. The trail is primarily used for hiking and snowshoeing and is accessible year-round. Dogs are also able to use this trail but must be kept on leash.

4.6 miles 1418 feet Out & Back

dogs on leash

hiking

snowshoeing

views

wild flowers

wildlife

10 days ago

11 days ago

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

hiking
23 days 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
23 days 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.

28 days ago

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

hiking
1 month 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
1 month 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!

hiking
1 month ago

hiking
1 month ago

Awesome time. Hike was steep but pretty easy. Heavily trafficked trail and parking at trailhead was a nightmare. Some idiot about blocked us in to our spot so beware.
Ruins were super cool and scenic view in Autumn was very nice. Firetower top was closed however.

1 month ago

Really bad pick for a first hike to get in shape, but extremely beautiful trek with amazing a real crown jewel of a view.

1 month ago

A consistent ascent followed by a consistent descent along a utility road marred by power lines. The view and ruins are nice.

1 month ago

hiking
1 month ago

LOVED this hike. We were two adults, one 14 year old and one 8 year old. Beware it is quite loose rocky in dirt type trail for most of the way so if you have wobbly or bad ankles beware or wear boots that give the ankle some additional support. The hotel ruins are AWESOME and we enjoyed exploring them. The overlook is actually quite small and quite steep drop off would be an understatement so if you are with dogs or small children keep hold of them before venturing out onto rock outlook. The views from the outlook majestic. There is a welcomed ranger station at the top with a compost toilet. after wandering up to the fire tower you will find a few picnic benches should you want to have a snack or lunch. the fire tower is steep and offers some cool views. There are port potties at the trailhead. The parking lot is quite small 20 cars perhaps?

hiking
1 month ago

2 months ago

Steep slope, beautiful hike. Old hotel ruin is gorgeous, fire tower and scenic overlook at the top is a must! Would love to do this again.

trail running
2 months ago

hiking
2 months ago

It is a decent climb straight up. If you are in ok shape it will be tough, but you can do it! The path up is blah until you get to the old hotel. Super fun! During summer the nats are thick. Bring a bug net for your head. The views on top the fire watch are great.

2 months ago

Great place not much to see on the way top. Hardly any parking be careful parking on the road because when we arrived the police were towing and handing out tickets. You can park on some parts of the road but just look at the parking signs. The people on top were awesome had Oreos and water. Make sure you donate and don't be a freeloader

2 months ago

One of my favorites! Amazing views.

hiking
2 months ago

9/15/16~71, sunny with a nice breeze. Wide gravel trail with the gradual upgrade starting out immediately. If you find it to be too strenuous, there's a few big rocks on your left you can rest on. For someone who's in good physical condition, you'll have no problem!! There are really no views on the trail until you get to the abandon hotel. The view from the fire tower was spectacular. Take the time to go on the trail to the "overlook" there's some interesting dates carved in the stones. The trail was busy with hikers, parking lot was full. Trail was well marked where needed, no wildlife to be seen. Runkeeper app said 4.66 round trip. Fire Tower #6/28