Overlook Mountain Trail

MODERATE 278 reviews
#1 of 61 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

14 minutes ago

hiking
1 day ago

1 day ago

Amazing view at the top!

hiking
5 days ago

7 days ago

Steep incline the entire way up, but worth it! The hotel ruins are fun to walk through...there's about .5 mile left from there to the top. Nice area at the top with the fire tower and picnic tables and bathroom...there are warning signs everywhere from the hotel to the fire tower to watch out for timber rattlesnakes, but we didn't see any!

hiking
7 days ago

Trip into the clouds with daughter and lab. Nice incline on gravel road. Not busy on weekday morning. Dramatic view but in the clouds today.

hiking
7 days ago

hiking
8 days ago

We arrived in the parking lot at 4:30 in the afternoon on a Saturday and were lucky to get a parking spot. Saw lots of people heading down while we were heading up, so we had more time in the hotel ruins and the fire tower and experienced less crowds. It was actually COLD at the summit-wind gusts were crazy. It was hard to believe for August! This hike is steep but worth the views. No timber rattlesnakes. The boys loved that the fire tower volunteer had Oreos at the top. Make sure you take the .3 mile to the natural overlook while up there.

hiking
8 days ago

Overlook is a staple trail in Catskill Park. I enjoy this trail early in the morning before the crowds. Its a nice and fairly quick hike that is well marked. If you visit the Woodstock area, Overlook is a must visit

hiking
14 days ago

hiking
14 days ago

Saw lots of wildlife including a timber rattlesnake(endangered), a juvenile bam eagle and some turkeys. Trail was steep and overpacked a little so it was harder than usual. Hotel ruins were cool and the fire tower was amazing. Go early for parking though!

hiking
15 days ago

Great view from lookout and fire tower. The hotel was really interesting.

hiking
15 days ago

We did this trail about 15 years ago and decided to come back with our kids. There is a decent sized lot at the trailhead, but 9:30am on a Sunday, it was full and people started parking on the road. Be careful, I have heard the town tickets a lot of cars there.

The trail is pretty straightforward - a wide trail with a steady ascent for 2.5 miles up to the top. There isn't a whole lot to see until about the 2 mile mark, where there is an abandoned hotel to explore. I was definitely feeling it as I am not particularly in shape (no time to work out) and the kids were complaining how they were tired. We took plenty of breaks and distracted them with raspberries along the side of the trail to pass the time.

At the top of the mountain, there is a Visitor's Center, Fire Tower, Overlook, and even an outhouse.

The Visitor's Center has exhibits, info on the abandoned hotel, rattlesnake skins, etc.

The fire tower is open to visitors (6 at a time). While it was a little nerve wracking to be up that high, it is sturdy and has a nice viewing platform at the top.

The overlook has more amazing views - just be careful especially with kids near the edge.

We did see a Timber Rattlesnake right on the side of the trail a few minutes before we reached the hotel. It was rattling its tail and slithered off into the bushes. I was surprised it was so big! There are warnings at the bottom of the trail and then a bunch of signs right past the hotel as well, so keep an eye out throughout the hike, and especially if you are walking around in the woods (e.g. top of the mountain, hotel area with plenty of areas for snakes to hide).

The trail was busy and there were even more cars parked up and down the road when we left. Also, the town of Woodstock was absolutely packed, with advertisements for $5 parking at the end of town.

hiking
16 days ago

hiking
17 days ago

17 days ago

Moderate, steady climb. Trail is a little dull but the Overlook Hotel and Fire Tower are worth it! Use the bathroom in Woodstock before coming to the trail head. Port 'o potties but gross.

hiking
17 days ago

hiking
17 days ago

hiking
17 days ago

I wouldn't say this trail is "easy" ... it's about 2.5 miles with a steady incline the entire time. It's not for the unconditioned, that's for sure.

Nice, wide stone/gravel path with ample areas to stop and rest. Friendly trail-goers all along the way.