Overlook Mountain Trail

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Overlook Mountain Wild Forest

Overlook Mountain Trail is a 4.6 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 best used from March until November. Dogs are also able to use this trail but must be kept on leash.

Distance: 4.6 miles Elevation Gain: 1,397 feet Route Type: Out & Back

dogs on leash

hiking

nature trips

snowshoeing

walking

bird watching

running

views

wild flowers

wildlife

snow

As of May, 2020, users have reported that the Fire Tower is currently closed. Please consult the park's website before visiting.

hiking
bugs
1 day ago

Great hike, lots of incline but absolutely no scramble. The fire towers closed but views are still wonderful. Lots of bugs

hiking
1 day ago

Hiked in late April. Loved this hike and wanted to get it in early before the rattlesnakes started taking over. the building is an awesome piece of history to explore along the way. fire tower was closed at this point but still an easy to follow trail and fun day hike!

hiking
bugs
1 day ago

This is definitely not for your average person hike. It’s all uphill but it’s stunning when you get to the top! The ruins are awesome!

4 days ago

The walk up is not the most exciting, it is basically following what used to be a road. but it is steady climb, not too steep but you will feel it. On the way there are the ruins of the old hotel which is cool to poke around in. The view from the top is incredible though. definitely worth the climb. I have done longer steeper hikes for much less impressive views.

hiking
no shade
rocky
6 days ago

Excellent view at the top. It’s so worth the entire walk up - incline all the way. Rated a 5 because I loved it. The only thing it was buggy. Nasty little suckers! They will go away so not to worry.

hiking
7 days ago

The payoff at the overlook and the unrelenting incline (on the way up) is the entire walk. The trail itself is just a carriage trail that goes up hill, surrounded by woods but a bit dusty and unvarying woods, with a significant number of people. I take this hike once every year or two, but its not my go to for a contemplative hike.

bugs
7 days ago

This hike was dooope!! A mental and physical challenge. It's a consistent incline the entire way up but I wouldn't consider it a steep incline. Just enough to really get you sweating. Definitely worth every step to get to the top!

hiking
bugs
7 days ago

hiking
bugs
7 days ago

The road to the top is nothing spectacular. But it’s a necessary evil in order to see the grandeur that awaits at the top. Bring plenty of water and go at your own pace!

hiking
bugs
8 days ago

Solid challenge. The all uphill climb will test you more mentally than physically. The views from the summit are supreme and more than worth the effort. Great spot for a sunset with friends.

hiking
8 days ago

Tough but rewarding trail. It’s one long trail straight uphill. Makes two miles feel much longer than it is but the view at the top is spectacular.

hiking
9 days ago

If you’re okay with an entirely uphill hike it is amazing. If you have any sort of respiratory illnesses please take care of yourselves and give yourself plenty of time to get to the summit. The ruins are massive and the summit view is completely worth it!

hiking
rocky
11 days ago

Entirely uphill, but once you're at the top it's worth it. There are really cool ruins of an old hotel near the summit. Parking was a bit of a nightmare, but there is a lot farther down the road with another trail leading to the main trail. The whole trail is a gravel road all the way to the top. Rattlesnakes are very common so be sure to keep an eye out and walk carefully. At the summit there were volunteers giving out food and water, as well as answering questions. There was also a small museum detailing some of the history of the area. I highly recommend stopping in for a few minutes to learn a thing or two. The fire tower was a great finishing touch to an already great experience. Pack snacks and water, because despite being a competent hiker I found the constant uphill climb killed my battery pretty quick.

hiking
15 days ago

The views are incredible at the top from the overlook area and the historic hotel ruins are amazing. The fire tower was closed but it gives us another reason to go back. Worth the drive.

17 days ago

Boring uphill climb on Fire Road, but well worth the climb. The abandoned hotel alone makes the hike great, but bonus on the other side are incredible views of the Hudson toward Kingston and the Reservoir I assumed was the Ashokan. Fun few hours. Windy at the top.

snow
18 days ago

nice hike, love the old hotel ruins

hiking
bugs
19 days ago

Great trail. Incline all the way up for the most part. A little rocky. Beautiful results when you get to the top, well worth the trek.

Absolute beautiful lookout and such cool abandoned hotel....incline the ENTIRE hike it was rough in my opinion but so worth it with that view!!!!

hiking
20 days ago

Touristy? Yup. Wild and adventurous? Nope. But this hike will always be one of my favorites. You gain elevation quickly so it’s a bit challenging, and get rewarded big time with views and the old hotel. Just long enough to feel like you’ve done something and not too long that your friends can’t come with.

21 days ago

The view from the top is wort it, but the hike to arrive there is not. Pretty boring and steep, in this season when there are no leaves yet it can be very hot. I suggest going later in the afternoon: less people and nicer light. The remains of the hotel are a bit creepy, but the fire tower which is closed due to Covid-19 is beautiful. Amazing view of the Ashokran Trail and the Hudson River.

hiking
snow
21 days ago

Stunning view when you get to the top. It’s worth it. It’s steep and when I was there windy and cold and it was snowing. But it’s worth it!

hiking
muddy
rocky
22 days ago

Great view and a cool, abandoned hotel on the way to the top.

walking
24 days ago

Awesome walk/hike! There was a large, old hotel foundation to explore, fire tower (closed at the moment due to Covid-19), and scenic views at the peak with large stones on the ledge to sit down and take in the sights for a while (perhaps enjoy a lunch?). It was a little strenuous to the top, but pack light and you should be good. In my opinion, the walk down was a bit more rough. Quite rocky, wear good shoes. Great for dogs with a lot of energy!!

hiking
bugs
muddy
25 days ago

hiking
bugs
muddy
26 days ago

hiking
26 days ago

Hard hike to the top but the old hotel and view are totally worth it!

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