Overlook Mountain Trail

MODERATE 1137 reviews

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

hiking
snow
6 days ago

Did this trail Monday. When we arrived at 10 there were a few cars in the lot and it was around 14 degrees. There were a few inches of fresh show on the trail from Saturday. Pretty straight forward hike up a road with a mild incline. The views are outstanding. On our way down we passed over 20 percent heading up. This place gets very crowded. We went on a Monday but it was MLK day so it was a holiday for most. I would avoid it on weekends. Parking lot was filled to capacity at 1:00pm

hiking
snow
9 days ago

Snow provided some traction for the ascent and descent. Got out early, so it was quiet. Ice under the snow kept us on our toes. The view, wow, just epic.

recorded Overlook Mountain Trail

icy
snow
11 days ago

Was a cold mid-January day and very windy, but a good hike with great views.

hiking
muddy
16 days ago

I hiked this in the middle of January on a seasonably warm day (high 50s, low 60s.) The trail itself was nice and wide but was pretty busy. The parking lot was packed. The trail was icy in some spots but not enough for spikes. It was also muddy, which made wearing hiking boots an even better idea. The fire tower had a decent line, involving a group of people just cutting in line. There was a pretty decent and unfortunate amount of garbage on the trail. This hike seems very much like a tourist destination and while I'm sure it's better in the warmer seasons and when it's less crowded, it was just an okay hike.

hiking
muddy
16 days ago

hiking
icy
17 days ago

Hiked with Dan. Overlook for winter credit. 54°F at start, 57°F at the end at 6pm, misty/drizzly the whole time. Wore microspikes at the top and all the way down, as we came down in the dark.

hiking
icy
23 days ago

hiking
icy
24 days ago

Mostly ice despite the moderate thaw in temps. Spikes recommended.

hiking
icy
snow
29 days ago

Great trail that’s really just a closed access road. Extremely icy - doable without spikes but took 3.5 hours in and out. Gorgeous reward at the top and still beautiful along the way.

hiking
30 days ago

3 stars but thats my own fault for not being prepared. The trail was totally iced over you need spikes. Hope to get back there again with the right equipment or better trail conditions so i can enjoy it more.

hiking
icy
1 month ago

Good trail for beginners but if you’re going in these winter months bring spikes because the trail is very icy. The scenic views are nice as well as the fire tower. The hotel ruins are nice too to explore.

hiking
snow
1 month ago

Very icy bring spikes.

hiking
icy
muddy
1 month ago

hiking
icy
1 month ago

hiking
1 month ago

Amazing trail! Make sure you’re prepared when doing it in the winter— hiking sticks, layers, snow pants, head gear, proper shoes, and gloves

hiking
icy
1 month ago

(Mid-December) The trail is really an access road but it proves for a moderately challenging hike until you reach towards the top where you see incredible abandoned structures and can climb the firetower for a 360 view. Great hike we had a blast!

hiking
snow
1 month ago

Great views at the top, trail is all packed snow.

hiking
1 month ago

A well manicured trail that is essentially a road— consistent incline throughout. Sheets of ice towards to top, LOTS of people even on a cold day. Only three stars because it didn’t really feel like a trail through the woods due to the road and people always around.

hiking
icy
1 month ago

Good uphill climb. Good views. Heavily trafficked

hiking
icy
2 months ago

Great hike. Not too difficult. Steady incline but not bad. Views definitely worth it, from both the fire tower and the viewing area. The ruins of the Overlook Mountain house were awesome to explore! Great day to spend with 2 of my kids.

hiking
2 months ago

Dog friendly and the ruins are pretty neat. No views at the fire tower proper, but there are views off of a side trail.

hiking
2 months ago

Beautiful sunrise view. There are inscriptions in the rocks at the overlook points dating back to the late 1800s.

hiking
2 months ago

Beautiful sunrise view. There are inscriptions in the rocks at the overlook points dating back to the late 1800s.

hiking
2 months ago

Beautiful sunrise view. There are inscriptions in the rocks at the overlook points dating back to the late 1800s.

hiking
2 months ago

Beautiful sunrise view. There are inscriptions in the rocks at the overlook points dating back to the late 1800s.

hiking
2 months ago

Beautiful sunrise view. There are inscriptions in the rocks at the overlook points dating back to the late 1800s.

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