Overlook Hotel Front Facing Ruins
Getting to The Overlook Mountain Trailhead
Nestled 3,140 feet, Overlook mountain is situated just a 2.6 miles north of Woodstock, NY, and features one of the regions most favorited hikes.
A sizable parking lot can be found at 353 Meads Mountain Rd, however, parking spots may be in short supply due to the number of tourists who visit the Overlook each day. Driving to the lot is no easy task either as it’s roughly a mile up the mountain to the lot from the small town of Woodstock. Make sure your breaks are in good shape for the trip back down.
Climbing Overlook Mountain
It’s 2.3 mile hike up the trail which can be a bit tough for less experienced hikers, but is very rewarding. This hike gives adventurers a breathe taking view of the surrounding landscape from the top. With the meat and beans of the hike being uphill, you may want to take your time getting up.

Most of the 2.3 mile trail is gravel and rock from the Limestone Bedrock with decent traction, but unsmooth surfaces, easy to roll your ankle on, unlike the Cornish Estate Preserve which featured a paved road up to the former Estate.

Be Aware of Your Surroundings, Snakes are Lurking.
Do be aware depending what time of year you visit, there are Timber Rattle Snakes in these woods and on these trails. It would be recommended to come with garters or high boots if you plan to go looking for the best shots and views.
Camping Near Overlook Mountain
Just past the Abandoned Hotel at the top there are also camping spots, from which you can steak a tent and hang with some friends by Echo Lake. We didn’t venture that far in, however we did see several large groups headed that way.
Make sure if you plan to camp you take a photo of the trail map, there are several designated spots to choose from, so if one is already taken, you can find the rest.
From Communist Utopia, to Tourist Trap
Overlook Mountain has a rich history of change and development. It once housed a hotel, Overlook Mountain House, which was one of the few “mountain houses” in the region during the 1800s.
The mountain also became the site of the Byrdcliffe Colony, an arts-focused utopian settlement, in 1902. Additionally, the Overlook fire tower, initially constructed in 1927, played a crucial role in spotting wildfires before being closed for safety reasons in 1988.
The mountain’s history includes multiple rebuilds and fires of the Overlook Mountain House, with the final closure and fire damage leading to its eventual ruins.
Is it worth Hiking Overlook?
Yes, and no. This Spot is absolutely a Gem, but your going to be dealing with a lot of NYC and Upstate NY folks heading to the same destination. This spot has become rather touristy and been shared a lot over the years. It’s worth a visit, but if you cant find parking there are plenty of other spots worth checking out!
JMA Rating
- Difficulty: 7/10, mainly uphill but after the big push its easy walking
- Views: 9/10, Plenty of spots to catch amazing views from, if your willing to wait or wade through people
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2 thoughts on “Overlook Mountain Abandoned Hotel & Fire Tower Trail: Two Rewards for a Single Hike!”