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    Home » Travel » Park + Trail Guides » New York

    Overlook Mountain (Woodstock, NY)

    Published: Nov 3, 2019 · Updated: Jan 15, 2022 · 2 Comments

    Want to go hiking in New York's Hudson Valley? Make sure to check out the Overlook Mountain Trail for amazing views, ruins of an abandoned house, and a fire tower!
    This post contains affiliate links. As an Amazon Associate I earn from qualifying purchases.

    Want to go hiking in New York’s Hudson Valley? Make sure to check out the Overlook Mountain Trail in the Catskill Mountains for amazing views, ruins of an abandoned house, and a fire tower!

    by Randy Shepard
    Overlook Mountain Views

    Planning on visiting the Empire State?

    While most envision concrete and skyscrapers when thinking of New York, there are some wonderful hiking opportunities. There are even some epic trails in and near New York City.

    A recent trip to the Hudson Valley led me to some amazing hiking trails, like the rock scramble up Bonticou Crag and (of course) Overlook Mountain. The Overlook Mountain Trail is perfect for a great day of exploring ruins, a fire tower and some amazing views.

    Make sure to do this hike on a clear day, because the overlooks are stunning.

    Looking for something to do after your hike? Check out the nearby Angry Orchard Cider House in Walden, New York, or make this part of a longer east coast road trip!

    Is this trail Difficult?

    The Overlook Mountain Trail is a 4.6-mile moderately difficult out-and-back-trail. The trail itself is not technically challenging, but it is quite steep.

    It’s an old carriage road that winds its way up, rising 1,370 feet in elevation in 2.3 miles before reaching the 3,140-foot mountain peak.

    Thankfully, there are plenty of rest areas along the way if needed.

    Gear Tip: The trail is steep, so a pair of trekking poles (like these Kelty trekking poles) would make the ascent easier.

    Where is the Overlook Mountain Trail?

    The Overlook Mountain Trail is located in the Catskill Mountain range, and the trailhead sits just outside of Woodstock on Meads Mountain road.

    While there’s parking at the trailhead, I suggest going a bit further down the road to park in the lower lot and then taking the spur trail back up. It’s a short hike, but is quite beautiful in its own right.

    Once you’re back to the upper lot and trailhead you’ll begin your ascent to the peak of Overlook Mountain.

    overlook mountain trail
    overlook mountain trail

    Hiking the Overlook Mountain Trail

    You’ll hike up, up, and up some more.

    Keep your eyes peeled as you hike: rattlesnakes are in abundance here.

    Rattlesnake Warning Sign

    Towards the top, you’ll come to the Overlook Mountain House ruins, an amazing shell of a former hotel that presents great opportunities for photos and exploring.

    overlook mountain house ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins
    Overlook Mountain House Ruins

    When you’re done with the ruins, continue on to the mountain peak. There, you’ll find a spur trail that takes you to the bluff for some unbelievable views of the Hudson Valley.

    Overlook Mountain Views
    Overlook Mountain Views

    You’ll pass a fire tower, but save that for last!

    You’ll see a few outcroppings here, so look for trails to the other less explored areas to the right.

    Head back to the fire tower, and climb to the observation deck (open on weekends) or to the highest landing, and then take in the 360-degree view!

    Fire Tower on Overlook Mountain

    Look to the west and you’ll see the ruins peering out from the trees.

    View of the Ruins + Fire Tower
    View of the Ruins + Fire Tower

    Then, when you’re ready, turn around and head back the way you came towards the trailhead.

    randy shepard

    About Randy Shepard

    Randy Shepard was born and raised in the Missouri Ozarks. He’s an amateur mycologist, an avid hiker and a novice mountain biker of the St. Francois Mountains. When he’s not on the trail, he’s on skates, being a consistently inconsistent inline goaltender. Follow Randy at @forest.factory.

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    About Sarah Trenalone

    Sarah is the primary creator at Champagne Tastes. She's a photographer, food writer and traveler, and is certified in Backcountry Kitchen and Backcountry Navigation from the Colorado Outward Bound School and Identifying Wild Plants from Backpacker.

    Reader Interactions

    Comments

    1. S Clem

      November 03, 2019 at 6:27 pm

      Awesome! You make me want to go there! Fantastic scenery!

      Reply
      • Sarah Trenalone

        November 03, 2019 at 6:28 pm

        I want to go too! Randy’s hike looks amazing 😍

        Reply

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