Overlook Mountain Trail

MODERATE 345 reviews
#1 of 66 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
1407 feet
ROUTE TYPE
Out & Back

dogs on leash

birding

hiking

nature trips

snowshoeing

trail running

walking

views

wild flowers

wildlife

hiking
8 hours ago

The view is amazing

hiking
13 hours 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
1 day ago

The trail isn’t hard mostly a graveled wife 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.

hiking
1 day ago

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2 days ago

hiking
5 days ago

Thoroughly enjoyed this hike. It might have been boring had it not been for the weather. This was my first time hiking in significant rain. Fog at the trailhead and stared straight into nothingness from the scenic view at the summit. It was really entertaining to see just a wall of white from the summit. The heavy rain caused a good trickle to form for the last half mile from the hotel ruins to the summit. It was a lot of fun testing the boots out in it.

hiking
7 days ago

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8 days ago

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9 days ago

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9 days ago

hiking
10 days ago

Great hike. It is a straight 2.5 mile incline to the top. but worth the view and plenty of places to stop along the way. Cool architecture about 2 miles up that is a fun spot to explore and take a breather before the final half mile.

We went early so it wasn't crowded but as we were leaving around noon the parking lot was pretty full. i would recommend doing it earlier if you prefer less people.

Cool monestary across the street from the parking lot which is fun to check out as well.

Not a difficult hike, just have to be careful going back down.

hiking
11 days ago

Steep but worth it! Great views of the area up top and some cool abandoned buildings.

hiking
15 days ago

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16 days ago