The first hotel built on the mountain was designed and built by 1833 as interest in tourism in the area increased. The structure was built with the intention to expand it, but was unable to compete effectively with the Catskill Mountain House.[5] The Overlook Mountain House, owned by Robert Livingston Pell and designed by Lewis B. Wagonen, opened in 1871. At 2,920 feet (890 m), it was at a higher elevation than the nearby Catskill Mountain House or other hotels in the area.[3] The hotel had capacity for 300 guests, and was destroyed by fire in 1875. The hotel was rebuilt by the Kiersted Brothers in 1875, and faced increasing competition from the Grand Hotel, Hotel Kaaterskill, and Laurel House. In 1921 was the site of a secret organizational meeting of what was to become the Communist Labor Party of America. The hotel again burned down in 1923, and architect Frank P. Amato was hired by owner Morris Newgold to redesign and rebuild it. This design was never completely built, as the hotel's elevation and lack of rail transportation made it difficult for customers to reach the site, compounding owner Newgold's financial difficulties. The State of New York acquired much of the land, and the hotel was boarded up in 1940. Further fire damage in the mid-1960s brought down a roof-top tower which had remained standing until that point. The ruins of the hotel are accessible from the main trail.

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