One of the many reasons that so many people fall in love with New York is because of our unbelievable mountain ranges. While there’s nothing quite like the
epic mountains that you’ll find up north in the Adirondacks, the Catskill region is home to some highly underrated trails that are worthy of your adventurous bucket list. If the insane Lemon Squeeze hike that I’ve previously written about wasn’t quite your cup of tea, there’s one mountain right in the town of Woodstock that may be a better fit for you!
A 5-mile out and back hike that will blow your mind before you even reach the summit, Overlook Mountain has a trail you'll want to take.
Pictured above you can see the parking lot for Overlook Mountain. While the lot is a decent size, parking can often be hectic due to the fact that this trail is quite popular. To avoid coming back to your car and finding a ticket on your window, make sure you arrive early and get a legal parking spot or take your adventure during the week when the trail is much less crowded.
How to get here: You'll want to use the address for the Buddhist Temple that can be found directly across the street from the trailhead parking lot. 335 Meads Mountain Rd, Woodstock, NY 12498
Peaking out through the mountain, before you reach the summit you'll find the ruins of an abandoned hotel.
on YouTube, you can see some amazing aerial shots of Overlook Mountain and the ruins of the Overlook Mountain House. Roughly 1.8 miles into the hike you'll discover the ruins of this hotel that once thrived in the Catskill region, the scenic getaway was known for having the highest elevation of any hotel in the area.
The skeletons of the Overlook Mountain House still stand today, making for the perfect place to stop and rest before you reach the top of the mountain.
Captured in the first of two pictures above, you can see the large staircase of the hotel that many like to make as their resting spot along the way. While the DEC advises visitors to only view the hotel from the outside for obvious safety reasons, many hikers take the risk of fully exploring the ruins.
So, what happened to the Overlook Mountain House? The hotel was originally built back in 1833 when the area became a popular place to visit, drawing in tourists with views from 2, 920 feet up in the mountains. Sadly, in 1875 the hotel was destroyed by a fire and to make things even more heartbreaking, this wouldn't be the last fire it would experience. That same year the hotel would be built back up once again, only to struggle with competing against nearby hotels.
In 1923, Overlook Mountain House would again find itself destroyed by yet another fire. After this second fire, plans to rebuild the hotel were made but never fully executed. It wouldn't be until 1940 that the state of New York would acquire the land and board up the hotel entirely. But unfortunately the abandonment of the hotel wouldn't prevent it from further destruction, once again sometime in the mid 1960's another fire would destroy the hotel and bring down its roof-top tower that had been standing for so long.
Once you're done exploring the ruins, you'll continue on the trail until you make it to the top!
Following the yellow markers, you'll make your way up the mountain on the old and wide carriage road. You won't have to worry about scaling large rocky surfaces or dealing with intense scrambling, but just because this trail was originally a carriage road doesn't mean you won't be put to work!
Many consider the trail to be moderate in difficulty, but make sure you come prepared with water and a snack because the steady incline can be tiring. For most of our visitors, this mountain takes a total of 3 hours to explore.
Cautious Warning: Something you'll want to keep in mind? Most of those who visit this trail will go the entire hike without seeing any creatures of concern, but the area near the hotel ruins and towards the summit have been known to be the home to many timber rattlesnakes. So keep your eyes pealed!
As if this mountain hadn't already won over your heart, at the top you'll be able to achieve unforgettable views from the 60-foot tall fire tower.
Personally, I love our mountains that feature fire towers at the top. It's just one more adventure to be had on the mountain that
allows you to get even greater views. If you're interested in seeing what other mountains in New York feature fire towers,
to read about our hiking challenges, one of which is the Fire Tower Challenge!
Sadly, the cab of the fire tower just recently closed for the year, but that doesn't meant you still can't climb up the fire tower! The actual tower remains open to visitors all year long and helps you achieve even greater views of the Ashokan Reservoir, Central Catskills and Hudson River.
Pictured above you can see the view from the top of the mountain from the fire tower. During our summer months this trail can be quite crowded, with less chaos during our off season. If you've never explored this mountain before, now is the perfect time!
Another way to make this hike even more unforgettable and breathtaking? Make it a little bit longer!
As if Overlook Mountain was already incredible enough, you make your hike even longer by taking the trail to Echo Lake, making your trip a total of 9.3 miles long! The views at the lake are stunning and a great way to enjoy an adventure by the water.