The remains of a former hotel sit near the summit of Overlook Mountain, which rises just over 3,000 feet above Woodstock, New York. Hikers often pause on the steps to rest before completing their 2-mile climb to the top. These ruins are what’s left of the third hotel built on this site.

The story of the Overlook Mountain Hotel begins in the early 1800s, during the height of the Hudson River Valley’s popularity as a vacation destination for New York’s elite. In 1824, the Catskill Mountain House set the trend for Hudson Valley resorts, prompting others to build competing establishments.

The Overlook Hotel, however, faced challenges from the start. Poor train access to Woodstock and reports of rattlesnakes in the woods discouraged visitors, let alone the long uphill accent to the destination. The first attempt at a hotel came in 1833, with a small lodge built by a developer who hoped to expand. Business faltered, and the lodge closed within a few years.

A new developer, Lewis Wagonen, tried again in 1871, constructing a grand 300-room hotel. But this effort was short-lived, as the building burned down in 1875. Undeterred, two brothers from Kingston rebuilt the hotel in 1878, only to sell it to Morris Newgold in 1917. The hotel burned down again in 1921, prompting Newgold to use concrete for his third rebuild, aiming for a fireproof structure. He also began adding a chapel, stables, and a private lodge for his family. However, financial struggles slowed progress, and parts of the resort were still unfinished in 1939. Newgold eventually sold the property to New York State in 1940.

Unlike most historic Catskills resorts, which were demolished after their decline, the Overlook’s concrete construction has preserved its ruins. While the luxury era of the Catskills faded in the early 1900s and many resorts closed in the 1930s and 40s, there are still remnants to be found throughout.

If you decide to visit, not only are the ruins fascinating, but if you hike just a bit further up, the lookout over the Hudson Valley is absolutely amazing! There is also a fire tower.