Overlook Mountain Trail

MODERATE 475 reviews
#1 of 79 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
1,394 feet
ROUTE TYPE
Out & Back

dogs on leash

birding

hiking

nature trips

snowshoeing

trail running

walking

views

wild flowers

wildlife

snow

backpacking
10 hours ago

Nice to have the hotel ruins as a destination and the extra half mile to the tower is worth it

hiking
4 days ago

Hike itself is a 1/5 stars (nonstop loose rock and gravel track at steep incline for 2.4 miles)
Ruins of the old Outlook Hotel are a 9/5 stars
View from the fire tour is 5/5 stars

Total Rating: 5 Stars

Very very worth the hike up for the views and attractions.

10 days ago

Amazing!

hiking
11 days ago

Awesome hike! This was a very well maintained trail and I would highly recommend it. While it is certainly not easy, it is still doable for beginners that are up for a challenge. The view and the hotel make it well worth it.

hiking
12 days ago

Really well maintained trail. Not a lot to sew until you get to the top. But the views are so worth it! Definitely recommend.

hiking
17 days ago

Well maintained trail. Not much to see until you get to the hotel and all up hill. Easier after hotel and the view makes it all worth it. Moderate difficulty, difficult for beginners but doable. Definitely worth the effort. Get there early it is a small lot and it fills up by 9 or 10 on weekends.

19 days ago

Great view at the fire tower. Lots of annoying flies. Really cool to walk inside the abandon hotel.

22 days ago

So awesome. Old hotel is really cool and the lookout tower at the top...scary but gorgeous. Not to mention proximity to adorable woodstock.

23 days ago

Such a great hike with beautiful views from the fire tower and the overlook. The abandoned hotel was neat to walk through as well. Overall, I highly recommend it. Just be cautious of Timber Rattlesnakes while trekking along.I didn’t see any while I was there but they’ve been sited often.

24 days ago

This hike was one of my favorites!Loved the abandoned hotel it was right out of a horror movie, so cool! Make sure you check out the scenic overlook, the view is amazing. The hike wasn't that hard at all, it took me a little under 2 hours to get to the top.
Also check out the amazing Buddhist monastery right across from the trailhead parking! Wonderful day even with the little bit of rain.

hiking
27 days ago

Great hike. Slightly crowded when I went but it was The Weekend and a beautiful summer day. Fantastic views from the top, not a lot to look at on the way up though, but overall a very pleasant hike

hiking
1 month ago

Great trail, great cardio workout. the view was amazing! Fairly busy trail. Just be careful at the top, saw 3 Timber Rattle snakes.

hiking
1 month ago

Excellent hike. Great workout if you go at a fast pace. Good workout just for a normal hike. Remains a favorite hike. Some say an occasional snake above the hotel to the fire tower. Worth going up the fire tower.

hiking
1 month ago

The view is worth the struggle to get to the top. Couldn’t get into the top of the fire tower. Make sure you go tot the scenic overlook. It’s one of the best views I’ve seen in NY. It’s almost strait up from the parking lot to the hotel ruins. The last 1/2 mile isn’t that bad.

1 month ago

Fun little short hike. Cool hotel. Fire tower view was great. Saw a big fat rattlesnake. Cool day for sure.

hiking
1 month ago

Loved this hike, steep climb the whole way up. Well worth it for the ruins and the views from the top as well as the fire tower!

hiking
1 month ago

Great fun hike with amazing views! Super close to Woodstock which makes it very convienent. It is uphill and a bit strenuous the entire way up, but the trail is really a very well maintained fire road so it's not too shabby. The views from the fire tower are amazing and make it all worth it. Total time was a little over 2 hours which included about 30 min of playing around the abandoned hotel building and the fire tower.

hiking
1 month ago

Brought the basset/beagle mix and we made it up and down in a little over two hours with picture stops. A lot of people, so the earlier the better. There are bears and snakes but with the amount of people using the trail, bears seem rare. No word on snakes though.

hiking
1 month ago

I am so happy I did this hike! The scenic overlook took my breath away. A few things for non-experienced hikers: I thought I was in okay shape but oh, boy, this hike will inspire me to work out a lot more. I read the reviews below that this hike was super easy, but going about 2+ miles uphill in hot (high 80s) weather, while flies were constantly swarming around me despite bug spray almost made me turn back around half way up. It was difficult for me to pause and rest since the flies would attack me the second I stopped moving. (Putting a bandana around my head helped stop them from buzzing in my ears, though. Next time I'll have to bring a bug net to wear over my face!) Anyway, I decided not to be such a wimp and keep going, and was thrilled to get to the hotel ruins - very cool. As mentioned above, the scenic overlook was absolutely incredible and the best part. The fire tower was open, and the wind up there gave me a wonderful break from the insects along with a beautiful view. I saw adorable chipmunks everywhere, no rattlesnakes although I kept my eyes open. I was glad to bring hiking poles for the rocky/muddy parts of the trail - although almost non of the other hikers I passed had poles. It took me a little over 3 hours round trip - I parked in the farther parking lot, which added distance, and I probably spent about 20-30 minutes at the overlook/fire tower. It took I'd definitely do this hike again but will be more prepared against the bugs, or pick a better time of day. (I did this 5p-8pm)

hiking
1 month ago

Great first hike of the season. Would rate difficulty level Beginner to Moderate. Took us 2.5 hrs (with a lunch break in between) from parking lot to peak and down. Make sure to check out stores in Woodstock after the hike!

2 months ago

awsome hike! first of the season, ran into a serious thunderstorm, pingpong sized hail, and multiple tornado warnings, had poncho, made it to safe refuge under brick stairwell at the hotel ruins and waitied out torrential hail, lightning struck the firetower and was the loudest most powerful thunder crack i hsve every expeirenced, what an exhilirating rush n dynamic added to the hiking experience, the hotel ruins were really cool, its rank it easy going on moderate but pace yourself and YOU CAN DO ITT!! ENJOY AND BE SAFE , Love n God bless

hiking
2 months ago

Very cool hike, the scenic overlook is absolutely gorgeous. My buddy and I reached the summit in about an hour, maybe a little less. We are both recently retired college athletes so we may have completed it quicker than most. There was definitely an abundance of beautiful scenery to look out at from the top and the abandoned hotel was also certainly cool to poke around in. Despite the fact that we spent probably twice as much time in the car as we did on the mountain, I would highly recommend this hike.

hiking
2 months ago

Honestly, it is not that bad of a hike. I wouldn't even consider it "moderate". Just a straight path up to the fire tower or scenic view point. It's a good hike. Bring water and stay on the path.

2 months ago

Great hike! Moderate grade for most of the hike, then flattened out for a while near the top. Enjoyed exploring the old hotel ruins - neat! Fire tower was cool as well, the top level is chained off but you can get most of the way up it.

hiking
2 months ago

Carriage road turned into a trail so very accessible year round. Very popular, so expect crowds. Have done this hike many times but the best is very early morning or when colder and after a good snow. Snowshoes or crampons needed depending on conditions. Up and back takes about 2-3 hours depending on how long you stay at the summit.

hiking
2 months ago

Definitely check out the scenic overlook beyond the fire tower. Great views from there as well as atop the tower, or at least to just below the top. The only drawback, for me, is that I prefer more of a hiking path than a seasonal roadway.

hiking
2 months ago

I hiked this with a few friends about a week ago. Overall it was a great hike, great views from the scenic overlook and of the hotel ruins. This was definitely one of the easiest hikes I’ve done, and I would definitely do it again.

hiking
2 months ago

Awesome hike! Not as good for a first timer or even a first hike of the year for someone who isn't in great shape, but definetly worth the leg pain! FYI out of the probably 30 dogs we saw that day, only 3 were on leashes, and we witnessed one dog fight and near altercation between groups because of it, so you might not want to take fido along, even on a leash, if he/she is dog agressive at all.

hiking
2 months ago

A nice hike to the ruins and Firetower. There was nice views of the Devils Path and Westkill Mountain. There was no snow or ice on the trail and the weather was perfect.

hiking
3 months 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

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