The Secrets of Woodstock Overlook

overlook-hotel-woodstockThe first time I hiked the Woodstock Overlook, I went with my friend Colleen and a French guy named Ferenz who produced music for Yoga videos. Ferenz lived at the base of Overlook Mountain, and told us that the Overlook protected its glory: the first time anyone hiked The Overlook, they were never able to see the view. The weather would deteriorate, or some personal misfortune would come squawking in on a cell-phone before the summit was reached. One had to hike it a second time for the mountain to reveal its gems.

Ferenz led us halfway up before the storm hit. We continued to the top, mounting the fire tower, which granted us the epicness of hurricane-force winds, but no view.

Colleen and I hiked it a second time a few weeks later, and the weather stayed clear.


This time,  I was making the trek with my friends Hollis and Christian, neither of whom had ever been to the peak. The weather report was clear, but I was keeping an eye out for clouds.

We parked near the Karma Triyana Dharmachakra, a Buddhist Monastery at the foot of Overlook. The monestary is the North American seat of the 17th Gyalwa Karmapa, head of the Karma Kagyu school, one of the most widely-practiced forms of Tibetan Buddhism.

After a 2-mile hike up a abandoned dirt road, we came upon the Overlook Hotel



The Overlook Hotel was originally constructed in 1871, to service New York City residents looking for a weekend retreat. It burned down soon after, in 1875. It was rebuilt, but struggled financially until it burned down a second time, in 1923.



A half-mile hike from the ruins brought us to the acme of Overlook. I glanced up to the sky. So far, so good.

The top of Overlook is a broad field cherried with a 80-foot fire tower at its center. The fire tower is open to the public (well, not to the public, but you can crawl up there easily enough).


Which is exactly what we did. The tower is not for the faint of heart, but we made it up easily enough.



And, not to shit on the tenets of hippie-dom, but the skies stayed clear and the cell phones stayed silent.


One thought on “The Secrets of Woodstock Overlook

  1. Pingback: The 10 Best Hikes in the Hudson Valley and Catskills

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