The Catskills: Overlook Mountain

This weekend, a few friends and I took a trip to Overlook Mountain, located near Woodstock, New York. It was one of the more satisfying hiking trips I’ve taken recently, both in terms of enjoyment and physical exertion.

The pathway up this mountain is a steep one, and it definitely isn’t for those looking for a relaxing stroll through nature. You’ll get your workout for the day hiking Overlook, and I strongly advise packing a generous amount of water for yourself. The way up, while strenuous, wasn’t completely horrendous – but the way down really demonstrates how steep the trail is. Add in all of the rocks, and the walk down is probably the roughest thing you’ll have to deal with here.

Once you start nearing the top of the mountain, there are a ton of things to do and see. The first exciting site you’ll pass contains the ruins of old hotels, which are in pretty study condition considering their age. There are lots of windows and a few staircases that are safe to climb on (using caution, of course). And there are some remnants of when these hotels actually functioned, including a fireplace and an old bathtub.

A bit further uphill from the ruins, you’ll reach the top of the mountain. There’s a small exhibit center, where hikers can read about the history of the hotels and view some badass looking rattle snake skins. When we visited, there were also two lovely park volunteers waiting with water and snacks – which is probably the nicest thing I’ve seen on any hike. So kudos to Overlook and their parks department for being generally awesome.

If you bear left from the exhibit center, there’s a fire tower that you can climb to the top of. It’s a fairly robust structure, but I totally chickened out going up – so no judgment if you skip this part. Even the views from the second or third tier are worth seeing, though. It’s gorgeous from that high up.

And finally, on the right side of the exhibit center are the cliffs – featuring one of the most breathtaking overlooks I’ve ever laid eyes on. Pictures don’t do it justice, but how can they, from around 3,000 feet up?

I 115% recommend hiking Overlook Mountain to anyone who is looking for nature spots in the New York area. Despite the difficult way up and down, it’s worth the effort. It’s definitely one of my favorite places to hike thus far, and the town of Woodstock is absolutely adorable if you have time to visit!

Oh, and just a warning for those who do hike this trail: There are rattle snake habitats on this mountain. You’ll see plenty of warning signs. We had the pleasure of having a snake friend cross the path right in front of us. So just be alert, and make sure you don’t bother them! Happy hiking!