Overlook Mountain (Woodstock, NY)

Want to go hiking in New York’s Hudson Valley? Make sure to check out the Overlook Mountain Trail in the Catskill Mountains for amazing views, ruins of an abandoned house, and a fire tower!

by Randy Shepard

Planning on visiting the Empire State?

While most envision concrete and skyscrapers when thinking of New York, there are some wonderful hiking opportunities.

A recent trip to the Hudson Valley led me to some amazing hiking trails, like the rock scramble up Bonticou Crag and (of course) Overlook Mountain. The Overlook Mountain Trail is perfect for a great day of exploring ruins, a fire tower and some amazing views.

Make sure to do this hike on a clear day, because the overlooks are stunning.

Looking for something to do after your hike? Check out the nearby Angry Orchard Cider House in Walden, New York.

Is this trail Difficult?

The Overlook Mountain Trail is a 4.6-mile moderately difficult out-and-back-trail. The trail itself is not technically challenging, but it is quite steep.

It’s an old carriage road that winds its way up, rising 1,370 feet in elevation in 2.3 miles before reaching the 3,140-foot mountain peak.

Thankfully, there are plenty of rest areas along the way if needed.

Gear Tip: The trail is steep, so a pair of trekking poles (like these Kelty trekking poles) would make the ascent easier.

Where is the Overlook Mountain Trail?

The Overlook Mountain Trail is located in the Catskill Mountain range, and the trailhead sits just outside of Woodstock on Meads Mountain road.

While there’s parking at the trailhead, I suggest going a bit further down the road to park in the lower lot and then taking the spur trail back up. It’s a short hike, but is quite beautiful in its own right.

Once you’re back to the upper lot and trailhead you’ll begin your ascent to the peak of Overlook Mountain.

Hiking the Overlook Mountain Trail

You’ll hike up, up, and up some more.

Keep your eyes peeled as you hike: rattlesnakes are in abundance here.

Towards the top, you’ll come to the Overlook Mountain House ruins, an amazing shell of a former hotel that presents great opportunities for photos and exploring.

When you’re done with the ruins, continue on to the mountain peak. There, you’ll find a spur trail that takes you to the bluff for some unbelievable views of the Hudson Valley.

You’ll pass a fire tower, but save that for last!

You’ll see a few outcroppings here, so look for trails to the other less explored areas to the right.

Head back to the fire tower, and climb to the observation deck (open on weekends) or to the highest landing, and then take in the 360-degree view!

Look to the west and you’ll see the ruins peering out from the trees.

Then, when you’re ready, turn around and head back the way you came towards the trailhead.