Overlook Mountain Trail

MODERATE 398 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

snow

hiking
1 day ago

This is an awesome hike to an old hotel, fire tower, and cliff overlook of the Hudson Valley. The kids loved this one. Check out our full write up which includes directions and other things to look for.
http://www.eastcoasthiker.com/trails/overlookmountain

hiking
1 day ago

really great hike, interesting hotel ruins and amazing views. It is uphill the entire way. If the lot is full, there is a bigger one further down the road, adding an easy .07 that takes you back to the main trailhead. We went in April, there was still snow, but melting, making for a very wet and slippery hike. poles were helpful going back down.

hiking
18 days ago

Great weather on Saturday March 31 brought us here past the ruins to the tower. Easy hike thee hours RT includes 30 mins summit time at both tower and the view reached from the right of the observers cabin. BRING Microspikes!! So much ice and frozen snow with holes. No one else had micros there had to be injuries from falls. So many people struggled. BTW leave the sneakers at home. Again so many. Properly prepare for this. Great rewards for those who do.

hiking
19 days ago

Don’t underestimate its rating. Yes it is an old road trail but it uphill the entire way. Micro-spikes would be a great option as it’s ice and snow. The trailhead parking gets packed quickly but they fluctuate in and out so I was able to hold off for 10 mins and someone coming off the mountain was leaving. Another great day spent hiking and this one gives you more then the fire tower the abandoned hotel and house are a cool addition.

hiking
20 days ago

Awesome hike! Uphill the whole way up. Definitely need microspikes this time of year. Very icy right now (March). The view is beautiful. Very very very busy trail. Get there early! Came off the mountain and the parking lot was full and a hot mess.

25 days ago

Fun trail ... nice views ... firetower wasn’t open but awesome trail ...

1 month ago

Trail is almost entirely melted after today’s weather ! It was a beautiful hike .. you don’t need spikes anymore unless the temperatures drop again. Will be going again soon

hiking
1 month ago

Beautiful hike to an abandoned hotel and a fire tower worth climbing. It’s definitely uphill but we did it with a chihuahua and he was fine!

2 months ago

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

Views are great but tower is closed .

hiking
3 months 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
3 months 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.

3 months 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.

3 months 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
4 months ago

Easy walk. Old hotel ruins are fun also!

5 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
5 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
5 months ago

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

hiking
5 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
5 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
5 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
5 months ago

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

Amazing views!

5 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
5 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
5 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.

5 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.

5 months ago

Beautiful October hike.

hiking
6 months ago

The view is amazing

hiking
6 months ago

Great hike that I as a plus size woman say is not very moderate as its mostly just a gravel trail, but the incline can be a challenge for some. Even passed folks with strollers! We arrived early around 830am on Sunday and lot was almost full. Coming down passed many folks but to us the more hikers the happier I am because people need to be enjoying our nature! View at top is amazing and old hotel is great to explore. Have an open mind when hiking and be glad to see others out. I could rate higher but I think it wasnt a difficult moderate hike (&I have hiked 46ers too) . View was bit in the clouds but its expected. Glad we drove the 2hrs down to do it.

hiking
6 months ago

The trail isn’t hard mostly a graveled wide path to the top, it is a pretty steady incline but most people could make it with no problems. The path was heavily crowded. PARKING IS A NIGHTMARE. Do not park anywhere other then the park lots or you WILL get ticketed. Other then that the views and the fire tower are cool and the abandoned hotel was awesome but with so many people it’s definitely harder to enjoy.

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