Located near the groovy town of Woodstock is a trail that leads up to the ruins of the Overlook Mountain House. No, not that Overlook where all work and no play made Jack a psycho boy. This one is far more benign, yet has its fair share of eerie vibes.
It was a swinging place to stay during the heyday of the Catskill vacation boom during the late 19th and early 20th centuries. The ruins that stand today were actually the third incarnation of the hotel. The original could house 300 guests, the most famous being President Ulysses S. Grant. After being destroyed by fire, another was built, and it too, succumbed to fire in 1923. Bad luck befell the last version of the hotel, which was never completed due to lack of funds and difficult access up the mountain. New York State owns the property today.
...and marvelous mountain views!
Exploring the outside of the ruins can be challenging due to the steepness of the mountain.
But I highly recommend it. All over the slope (and I mean ALL OVER) are bits of debris - porcelain, glass, metal - sticking out from under leaves or half-buried in soil. Lift any rock and you'll discover cool stuff underneath. You'll also find quasi-shrines of found treasures on just about every rock surface.
More information about the Overlook Mountain House has been unearthed here.