Overlook Mountain Trail

MODERATE 381 reviews
#1 of 71 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

20 days ago

This was such a great adventure!! Please bring micospikes. At least for no anyways .

Views are great but tower is closed .

hiking
1 month ago

We did this trail on the last day of december, it was cold and snowy with some ice. A good pair of microspikes is a good idea. It was -20 at summit so be prepared. Im in decent shape, very active and this is definetly a good incline but not unobtainable for the average. If your adventurous do the hike a hour and a half before sunrise and greet the sun from rock overlook just around bend from the ranger station. This hike is in my top favorites thus far as it gains elevation, its not long in distance, the view at overlook and firetower, the ruins of the hotel, the history in the catskill range, absolutely worth every step! The buddist monastery at parking lot is a great bonus. Safer in winter than summer for off trail exploring due to the rattlesnakes in summer so i hear, and you cant park anywhere but the lot so get there early or at less popular times.

hiking
1 month ago

The views from the top are fantastic. It’s good if you want a moderate out and back for exercise, but aesthetically it’s not outstanding. It’s a road with power lines.

1 month ago

Great quick and challenging hike! Ruins are pretty cool too! Be sure to get there early as the parking lot fills up quick and the local police fine people if they park on the road. I've heard the fines are quite pricey too.

1 month ago

Went on December 24 & the trail was covered in a sheet of ice. Bring shoe spikes! It’s not a difficult trail (slow elevation gain for 2.5 miles then back down) but the wintry conditions made it more interesting. Nice view of the Hudson from the top.

hiking
2 months ago

Easy walk. Old hotel ruins are fun also!

3 months 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
3 months 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.

hiking
3 months ago

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

hiking
3 months 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
3 months 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
3 months 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
3 months ago

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

Amazing views!

3 months ago

Best view for little mileage!

The trail is straightforward and the terrain is pretty easy considering it’s wide enough and not too rocky.

I brought my maltese with me and she had no problems but was pretty exhausted halfway going back, but then again its her first REAL hike outside of her city walks.

will definitely do again!

hiking
3 months ago

This is a beautiful view at the top! It's challenging, this was my first hike up a mountain and I was really struggling. The trail is very rocky and for the most part uphill, it's challenging but no impossibly, there was a 20 month old baby and miniature dogs hiking up so it was good motivation.

hiking
3 months ago

My first ever hike on a sunny Friday morning. It was beautiful, a little steep in the beginning, which was a good challenge. The view was unbelievable. I look forward to doing it again in the future.

3 months ago

Maybe the best view I've ever seen in my life is at the top of this hike. Definitely best view in upstate New York that I've seen. You can see all of the Hudson valley and a lot of the Catskills mountains. I'd definitely take visiting friends on this hike.

3 months ago

Beautiful October hike.

hiking
4 months ago

The view is amazing

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