Overlook Mountain Trail

MODERATE 375 reviews
#1 of 72 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.

DISTANCE
4.8 miles
ELEVATION GAIN
1394 feet
ROUTE TYPE
Out & Back

dogs on leash

birding

hiking

nature trips

snowshoeing

trail running

walking

views

wild flowers

wildlife

hiking
2 days ago

hiking
9 days ago

hiking
13 days ago

Easy walk. Old hotel ruins are fun also!

hiking
17 days ago

18 days ago

hiking
24 days ago

hiking
24 days ago

25 days ago

Nov 4 2017 great views old mountain house hotels firetower and apparently if you go during warm months there is a large habitat of timber rattlesnakes near the fire tower so if you go when it’s warm be careful near the top with children and pets. Can also continue trail to echo lake and some other trails to another parking.

hiking
1 month ago

hiking
1 month ago

Great workout. Yes, it’s a very long and steep grind up a gravel road - but the rewards at the top make it worth it!! The ruins are incredible and the views from top a tad further are a must see.

1 month ago

hiking
1 month ago

hiking
1 month ago

Steep uphill on gravel for first mile or more. Gorgeous views from the lookout.

hiking
1 month ago

This is rated moderate because it’s literally straight up a gravel path. The history that comes along with the hike is a bonus. Make sure you’re on the lookout for timber snakes, but as long as you don’t bother them they will leave you alone.

I went at 5:15 to watch the sunrise and I’m so glad I did, it was a breathtaking view from the fire tower.

hiking
1 month ago

hiking
1 month ago

This is a very active trail. Beautiful views along the way.
I would classify this as more than Moderate. It's pretty steep and rocky along the way. When you reach the ruins of an old hotel the climb is getting easier. At that point you are about 1/2 mile from the fire tower. There is also a scenic lookout just a few step from there. Great hike!

hiking
1 month ago

hiking
1 month ago

It was amazing! The first 2 miles are all pretty steep incline. I consider myself to be pretty in shape but had to take a few breaks to catch my breath on the way up. 2 miles in is the old abandoned hotel, then another .5 to the top. At the top is the fire tower, and another scenic lookout point. A few things that I didn’t see in the reviews (maybe I just didn’t read all of them) were that there a lot of rattlesnakes. There are a few signs that warn you about the snakes at the top. Also, another cool thing is that there is a volunteer guide that was at the top of the mountain. I can’t wait to go back!

hiking
1 month ago

Very steep incline the whole way up this hike but very worth the views at the top

Amazing views!