Dispatches From Overlook Mountain Vol. 2

The Ghosts of the Overlook

A recent hike up to Overlook Mountain Fire Tower in Woodstock, NY, provided fodder for a whole string of stories - honestly it was one of the most adventurous hikes that I can recall in a long time. So, in an effort to give that all to you in bite-sized pieces, this week we’re presenting a series we’re calling Dispatches From Overlook Mountain. Part 2 is today. I hope you enjoy!

The trail to the fire tower actually swings to the left at this spot, but a hiker can walk straight through the ruins if they wish

Part 2 - The Ghosts of the Overlook

There’s no dearth of information regarding Woodstock’s (and perhaps the Catskills) most famous ruinous hotel near the summit of Overlook Mountain.

The ruins that remain of the Overlook are the hotel’s third iteration, the first built all the way back in 1833. That lodge was, apparently, the destination of the final hike of the famous landscape artist Thomas Cole.

The lodge was not successful. It was expanded in 1871, was also not successful, and burned down in 1875. It was rebuilt in 1878, failed to be successful again, and burned down in 1921. This time, so the story goes, a mob burned it down in the middle of the night after hearing about a secret meeting at the hotel of the Unity Club, the forerunners of the Communist Party of America.

It was rebuilt again in 1923, this time out of concrete to prevent it from burning down. The hotel was, you guessed it, not successful, and abandoned uncompleted in 1940 when the owners sold the property to New York State.

Date unknown, but pre-mid-1960s before the roof collapsed

These days, I’m willing to bet that what remains of the third Overlook is likely more popular than it was when high end guests were being driven to the top in a carriage.

The concrete part was a good idea by the way as the ruins that remain today are very nearly exclusively the concrete skeleton of the sprawling resort. The Overlook is one of the only examples remaining of these classic Catskill mountain houses, despite the fact that it’s gutted. Hikers are in for a treat.

After a two mile hike and designed to face the carriage road, which is now the trail, the hotel comes into view a long ways away and the straight-away trail gives you the option of climbing right up the walkway and right into the hotel. (The actual trail swings left and takes you around the ruin.)

The outline of what used to be the fireplace in the grand lobby is still clear

Not a lot of spooky factor here (maybe in the fog or bad weather), just dozens of hikers taking snack and water breaks on the steps, stairs, window sills and other fine lounging spots. (I had to be very patient to get pictures with no one in them.) One hiker came up with a drone that was buzzing about the ruins. And old horse trough still remains around the back and the outline of the grand fireplace is clear.

I spent some time crawling around the site, chatting with hikers and generally marveling in the shadows of the ruins. There are signs everywhere in this part of the Catskills that warn about rattlesnakes but I’m guessing it’s too busy in the ruins themselves for rattlers to have an interest.

After a bit, I moved on, thinking that the ruins of the Overlook Hotel would be the highlight of my day. Boy, was I wrong!

Tomorrow: Letting the Bells Lead Me

No floors here, one misstep and down you go