Overlook Mountain Trail

MODERATE 1077 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
4 days ago

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

hiking
10 days 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
12 days ago

Good uphill climb. Good views. Heavily trafficked

hiking
icy
19 days 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
26 days 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
26 days ago

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

hiking
26 days ago

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

hiking
26 days ago

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

hiking
26 days ago

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

hiking
26 days ago

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

hiking
icy
snow
27 days ago

29 days ago

Loved it!! The steep incline hike was totally worth it. Came across a Tibetan Monastery towards the beginning of the trail, explore the Hotel Ruins, and a Fire tower to catch a stunning view.

hiking
1 month ago

Great views from overlook. Lots of steep inclines first 1.5miles. Wide trail. Hotel ruins pretty unique and cool. Then overlook view is gorgeous. Keep walking to fire tower. Cooler up top also cool views and a picnic table with grill. Hiking poles helped. Enjoy! Oh porta potties don’t have teepee FYI. I came on a Wednesday around 11am; plenty of parking.

hiking
muddy
1 month ago

Arrived at trailhead 8:15 Sunday morning and parking lot was almost full. Steep yet steady grade for first mile and half then less steep to the amazing Overlook House ruins at approx 2 mile mark. Another 1/2 mile to the fire tower. Be sure to check out the ledge view behind the caretaker cabin. We found a picnic table at the third viewing spot. The tower cab was closed yet the view from the highest platform was outstanding. And windy. 90 minutes to reach the tower, 30 minutes snack and photo taking and 60 minutes back to parking by 11:30. This hike is very do-able for 63 and 65 year olds and is one of the five Catskill Five Fire Tower Challenge.

hiking
1 month ago

It was beautiful to be among the clouds

hiking
blowdown
muddy
1 month ago

hiking
muddy
1 month ago

hiking
muddy
1 month ago

I found this trail challenging just from the sheer distance (about 2 miles) uphill, though the trail had no difficult obstacles to get around and it’s impossible to get lost since it’s very well groomed. But the challenge was well worth the breathtaking views at the top and the very cool resort ruins.

hiking
1 month ago

This is a high traffic and easy hike offering a number of view points, hotel ruins, and fantastic 360 degree views from the top of the tower.

hiking
1 month ago

so worth the steep hike. The hotel ruins and amazing views are worth it!

hiking
muddy
1 month ago

hiking
1 month ago

Well worth the hike! The trial has some moderate to steep sections but not bad for a 100+ year old horse and buggy road (later used for jeeps). The views, cliffs, ruins, fire tower and wildlife make this a must hike trail if you are in the area. The firetower is only open on saturdays generally. The mountain house ruins are incredible and are almost 100 years old (1928). Just down the road from the mountain house ruins are the remains of two old cabins that are located along an old trail/road off of the main road (not the one with a power line going down). This trail is partially grown in but still discernible. Parking is a pain here if you get there after 10am during the week and most of the time on the weekends. Parking lines are found on the guardrail and if the vehicle is just a little sideways it will take up two spots. This trail is also a carry-in/carry out facility so please keep that in mind.

hiking
muddy
1 month ago

Had a few slick muddy spots, usually at a water run off crossing, had been a bit rainy the last couple days before. Bring some water, dress in layers. Porta potties at the base. parking is tough, we arrived around 11 am, one spot in parking lot, cars all along the road, steady flow of people. Steep incline, pretty constant. Great walk, amazing views, we didn't climb the fire tower, there was a huge line. We did follow the 'view' sign by the brown building and got a pretty good view though :) Steep on the down, take it slow, loose rocks, gravel and leaves (we went in fall, amazing foilage!) make it a little sketchy heading down.

hiking
1 month ago

The mixed reviews are quite funny. This is obviously a trail that all skill levels have attempted. I’m not a fast hiker by any means, but this only took us less than an hour to summit. This is not a difficult trail. Yes it is an incline all the way but you’re climbing a mountain so that’s to be expected. This is an old dirt road, so there aren’t any rock scrambles or stumps you have to dodge. Very easy. I give it 5 stars and look forward to coming back. The ruins are absolutely breathtaking and the summit is beautiful.

hiking
1 month ago

The trail is usually pretty crowded according to locals. I got lucky and went on a day with fog and rain which made it quieter and created an eerie energy through most of the hike which was awesome! The old ruins are really cool to see and the fire tower was exhilarating to climb. I gave 4 stars because most of the trail is just ascending up and old overgrown road with no change in scenery until you get to the summit.

hiking
1 month ago

I did this short hike on 10/19. The weather was very nice and the trail was very crowded. As someone else had stated, this is more of a steep dirt road than a trail, which makes it very accessible. That said, the building ruins near the top are worth the trip up. The views from the fire tower are really great as well.

hiking
1 month ago

Be aware, this trail is 2ish hours (depending on your pace) of only uphill incline. Other than that this trail is great! My buddy and I took a break at the hotel ruins, and I recommend you do too. Once past the ruins, it's another .5 miles to the top. There are two great vantage points up there, the first is facing the Hudson river and it is beautiful, but be aware of the cliff edge. The second is the fire tower at the summit. Overall, this was a pretty great hike, I started about 12, ended about 4ish. It's that perfect pre dinner exercise you'll need if you plan on eating in Woodstock. Note: Pay Attention to all Trail signs and markers. This is rattlesnake territory.

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