New York's Once-Luxurious Hotel Hides In A Scenic Catskills Trail With Abandoned Ruins And Hudson River Views

Upstate New York is home to several historic luxury hotels that continue receiving guests today. There's the grand Mohonk Mountain House, a Victorian mansion built in 1869 overlooking a glacial lake in the Hudson River Valley. Then there's the glamorous Oheka Castle on the highest point of Long Island — the French-inspired chateau and its manicured gardens were the setting for Great Gatsby-style parties in the 1920s. But one of the region's most legendary old hotels, the Overlook Mountain House, has been sitting abandoned for years.

So what's the story behind this mysterious landmark tucked into the woods near the peak of Overlook Mountain in Woodstock? The first building on the site was a 19th-century inn that hosted New Yorkers looking for an escape from the big city. Framed by lush foliage near the mountain's summit and featuring views of the Hudson River, the hotel was indeed surrounded by nature, but it was also inconveniently located for travelers: train service to the area from New York City was comparatively limited, especially in comparison to other options in the region. 

The inn changed ownership a few times, underwent renovations, and burned down in a fire in 1875. The hotel was quickly rebuilt, but in 1921, it perished in flames once more. After a third attempt to rebuild and expand, the owner ran out of funds, and the project was abandoned in 1940. Today, it belongs to New York State, and unlike similar properties in the region that were demolished after closing, the Overlook Mountain House's concrete walls have stood the test of time. 

Since the hotel's ruins are right beside the hiking trail that leads to the summit of Overlook Mountain (a 4.6-mile out-and-back route from the trailhead outside Woodstock to the top, which takes around three hours to hike), the historic site sees a fair amount of foot traffic. If you look closely at the building's façade, you'll spot "1928" — the year the hotel was almost finished for the third time — carved into stone. Step into the main hall and gaze up at the trees growing through the now-vacant spaces, once elegant salons for dining and relaxing. If you love the Catskills, consider a detour to New York's best ski resort, a premier family-friendly getaway. 

Access to the Overlook Mountain House is only on foot. You could walk or drive from Woodstock to the Overlook Mountain trailhead (one hour on foot or seven minutes by car) and hike up (about one hour), even if you're not doing the full trip to the mountain's summit. Be sure to bring water and snacks. A quirky, artsy town full of farm-fresh food and cozy charm, Woodstock has a good variety of dining options, including the stylish Pearl Moon Woodstock and the Red Onion, located in a historic farmhouse. Woodstock Way Hotel ($389 per night), with rustic-chic rooms in a wooded setting, is a great choice for an overnight stay.

The closest major transport hub is the Amtrak station in Rhinecliff, about 30 minutes from Woodstock by car. From there, it's a 1.5-hour journey to New York City and its international airports. If you're continuing your exploration of the area, check out the New York hamlet between the Catskills and the Poconos known as the "pizza capital of the Upper Delaware River."