One of the most intriguing and historical hikes around is at Overlook Mountain in Woodstock, there is just something so mesmerising and enchanting about abandoned places. Overlook Mountain has long been a significant location in New York. In the boom years of New York City after the Civil War, more than 90 quarries in the Town of Woodstock (many around Mount Overlook) produced bluestone for sidewalks in Manhattan. By the end of the 19th century, the mountain and surrounding area became a tourist location for New Yorkers escaping the woes of city living, looking to breathe in the fresh mountain air up the Hudson. The current ruins Overlook Mountain House was actually the third hotel on the site. The first Overlook Mountain House was built in 1871 and accommodated 300 guests, before it was destroyed by fire in 1875. It was rebuilt in 1878 by the Kiersted Brothers of Saugerties. Overlook was used irregularly between 1887 and 1917, when Morris Newgold of Manhattan purchased the hotel. In 1921, it was the site of a secret organizational meeting of what was to become the Communist Labor Party of America. The second incarnation of the Overlook Mountain House was destroyed by fire in 1923. And Morris Newgold sought to rebuild with fireproof construction.
His architect used concrete to rebuild the hotel, which likely would have been covered with stucco. They also broke ground for a chapel, stables, and a standalone lodge for private housing for his family. Newgold’s shaky finances paired with the Great Depression made for slow progress, and portions of the resort were still “under construction” as late as 1939 (and the main hotel never being finished from what I could find). Morris Newgold died in 1940 and the property was either sold by his son or acquired via eminent domain by the New York State Conservation Department and made part of the Catskill Forest Preserve. You can now explore the old ruins of the Overlook Mountain House between views of the Catskill Mountains.