Overlook Mountain Trailhead — Attraction in Town of Woodstock

The main parking lot was full, but there's a secondary parking lot about half a mile down the road. From there it's a mile through the woods to the gate. Not a bad walk. Actually, it's a good warm-up for the big climb. The trail is wide, more of a fire road than a trail. It's all vertical until you get to the top. Some spots are harder than others, but there are boulders alongside the road for breaks if needed. There was a pretty steady flow of people going up and down the mountain. The old hotel is pretty interesting and you can walk all around it. A short hike on a less vertical hill from there and you reach the fire tower. It was open while we were there, so you can climb up in for the best views of the area. It's well worth the hike up and back down. There were about 4-5 volunteers up there that helped guide people around and tell people about the tower and cabin. Every one of them were friendly and helpful. Dogs are allowed on the trail while leashed. We ate lunch on the cliffs just North of the cabin, then headed back down. We also stopped at the cliffs between the fire tower and hotel. It's a small secondary trail that's easy to miss. From the main trail it just looks like there might be a view of the valley if you walk a short distance through the woods. When you get out there the area is clear with a great view. Below that cliff you can see the remains of a plane crash back in the '70s. Overall, we probably spent about 4 hours up there. Great day trip for anyone that can make the hike. It's a lot of work, but the views are amazing and well...

VERY STRENUOUS HIKE. The first almost 2 miles until you hit the ruins is steep uphill hiking on a gravel road. For a popular hike in the Catskills, you definitely have to be in good shape for this one. The trail is wide enough to take plenty of breaks along the way so it’s doable for everyone going at their own pace.

The ruins are beautiful. It looks creepy and picturesque. Definitely good for photo ops. If you keep hiking past the ruins, it’s about a mile to the fire tower. You can climb up the fire tower and get some good views. You can continue along the trail and you’ll hit the scenic overlook. The views are amazing and definitely made the 2 mile climb worth it.

Parking is a little iffy. Get there early on the weekends to find parking. However I went on a Thursday 1pm and was able to find parking on the side of the road. There is a Buddhist Temple across the street from trailhead that looks interesting too.

The reason I am giving this 4 stars instead of 5 is that there is a lot of foot traffic since this is a popular hike but the views are...

Thousands of people walk up Overlook Mountain each year. I can’t think of a walk where you get such a good view for an easy 2.5 mile walk to the firetower. This was a rainy morning day in early October. We planned it to get started just as the rain stopped so there were only a few other cars in the parking lot.

This parking lot fills up early. Mead Meadow is a second larger parking area down the road. The Extension trail goes 0.7 miles from the Mead Meadow parking lot to the trailhead so you don’t have to walk on the road to get to the Trailhead. This is a fire road and trucks drive up it to the antenna tower two miles up the road.

There is an outhouse behind the building near the firetower. It was near full but in decent shape and had toilet paper and hand sanitizer.

We walked up to the Firetower and the lookout just past the Firetower. It was 1,400 feet of elevation gain. The lookout has amazing views of the Hudson Valley from Ashokan Reservoir to the...