Overlook Mountain Trail Hike

Overlook Mountain is located just north of Woodstock, NY. In fact, if you walk down the main thoroughfare of Woodstock, you can see it clearly. It’s a popular trail — one of the most popular in the Catskills, in fact. You won’t get any solitude but that’s because the payoff is amazing. 

Three payoffs, actually. There’s an abandoned hotel about 15 minutes from the summit — more on that later in the article, but it’s cool. Very cool. Then there’s the overlook itself, a rock outcropping that provides a broad view eastward over the Ashokan Resevoir and the central Catskills and over and beyond the Hudson River itself. Then, there’s the firetower, which with another 60 feet of climbing up the stairs, provides a pretty amazing 360-degree view. No, I didn’t climb it — a fear of heights AND a pretty stiff wind dissuaded me from even trying.

Although AllTrails.com, which I often use as my guide, lists the trail as “moderate,” I’d say it’s pretty strenuous for an average hiker. It’s straight up — and I do mean UP — for 2.5 miles, and for 1397 feet. It took me more than an hour and fifteen minutes to get to the top; my companion, who’s in better shape overall than me, made it up in about an hour flat. I was passed by three individuals; my companion wasn’t passed by anyone. I think anyone can do the hike — just take your time, go at the pace that allows you to breathe, take frequent rest stops if necessary. 

For the first third of the hike, you follow a former carriage road, now graveled and lined with electrical poles, up the side of the mountain; there are frequent switchbacks, and just when you think, “omg, this has got to be it,” it goes on for another five switchbacks. Some of the switchbacks are pretty steep and then it levels out ever so slightly, allowing hikers to catch their breaths and gird up their loins for more of the same. 

The forest on the way up is dense, but at the peak of autumn foliage color, it was gorgeous, with a dominating yellow leaf that made the forest glow. There’s enough noise from the other hikers (although frequently I was solitary on whichever switchback I was walking up at the time) that getting to see wildlife is probably pretty rare, although signs warn of bears and rattlesnakes.

Soon though, as you climb up the mountain, you notice that you can see sky through the trees and forest along the road, first on the left, and then a switchback brings you around the mountain and the view through the trees is on the right. 

Another few switchbacks, and at 1.6 miles and having accomplished an astounding 1157 feet of elevation gain, you encounter the ruins of the hotel, the windows and doorways gaping at you like a the head of a corpse-like monster, with empty eyes and a screaming mouth.

 The forest is reclaiming the hotel — only four outer walls and main staircases of the hotel and the nearby lodge are visible. Trees are growing inside the building, and the bright yellow leaves made it seem as if the light of chandaliers and electric lights were glowing through the empty windows. 

People really want the Overlook Mountain Hotel ruins to be haunted. Someone even conducted (and put it up on YouTube) a ghost hunt that was boring enough that I didn’t watch very much of it. There are no ghost stories about the hotel; it doesn’t seem as if anyone has died up here. But it should be haunted. It would be so fitting.

Honestly, I think someone ought to make a movie about the ruins — oh wait, someone did. Stephen King called his haunted hotel “The Overlook” in The Shining. Yeah, I know King’s haunted hotel is in Colorado, but I wonder whether the real Overlook Mountain Hotel might have somehow inspired him.

The Overlook Mountain Hotel was damned from the start. The ruins are of the third building, never fully completed, to be built on the site. The first, a cozy luxury lodge, opened in 1833 to entertain the fashionable elite, mostly from New York City, who were lured by the writings of Washington Irving and James Fenimore Cooper and the stunning Catskill landscapes by Thomas Cole. But the railroad service to Woodstock, was poor and made the hotel pretty inaccessible, and with few visitors, within a few years, the lodge closed.  

But still, someone thought it was a great location and decided to expand the hotel and it re-opened in 1871; the new hotel offered 300 rooms. It had just enough time to entertain former President Ulysses Grant in 1873 before it burned down completely in 1875. Grant and other notables, made the place popular. New entreprenuers rebuilt the hotel in 1878 and President Chester Arthur visited. It was sold to new owners prior to the start of WWI, but the hotel burned down again in 1921 or 1923. The owner decided to rebuild in concrete, but with the decline of the popularity of the Catskill resorts, financial problems, as well as WWII, the new — and fourth version of the hotel — never was completed. The state of New York gained the property in the 1940s. A final fire in 1970 destroyed what was completed of the new hotel, leaving the concrete shell we see today.

You’re not supposed to explore the ruins — there are dangerous drops, and the walls are not stablized — eventually they’re going to collapse, and eventually someone is going to get themselves pretty badly hurt, if they already haven’t been. But I couldn’t resist, nor, it seems, can anyone else. But if you do get hurt, you’ve been warned and you only have yourself to blame.

After you finish exploring the ruins you’re not supposed to go into, you only have another 240 feet and six-tenths of a mile to climb to get to the summit. 

During the exploration and selfie-taking of the hotel ruins, you’ve regained your wind and energy, and so this part of the hike, which is spectacular by the way, doesn’t feel hard at all and suddenly you’re at the summit. Keep your eyes peeled — you’ll pass more ruins, which looks like a small house.

At the summit you encounter a cabin; a sign indicates a spur trail to the right of the ground cabin takes you to the rock outcropping overlook. Go there first, you won’t be disappointed. 

Notice the graffiti, that dates as early as 1910.

Then head over to the fire tower. The cab is open most weekends between Memorial Day and early October, as is the ground cabin. From the top, on a clear day you can see six states: New York, of course, but also Connecticut, Vermont, Massachusetts, New Jersey, and Pennsylvania.

Know before you go: Although parking is plentiful, the hike is one of the most popular and so you may have to wait for a space. Be respectful and DO NOT park or block in the Tibetan Monastery opposite the trail head.

Getting there: 353 Meads Mountain Road, Woodstock, NY 

Hours: Dawn through dusk

Website: https://www.dec.ny.gov/lands/73982.html

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A photo taken by my hiking companion from the fire tower, about four flights up.