The 7 Best Hikes Near Woodstock NY

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best hikes near Woodstock NY: catskills sunrise/sunset view

Overlook Mountain’s massive dawn shadow

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Searching for the best hikes near Woodstock, NY? Look no further. Perfect for families and beginners, these trails offer scenic vistas, easy walking paths, and a glimpse into the captivating history of The Catskills.

Known around the world for its bohemian spirit and laid-back atmosphere, Woodstock is a haven for weekend adventurers seeking a perfect blend of outdoor recreation and cultural experiences. Stroll along the quaint streets lined with art galleries, boutique shops, and cozy cafes, or catch a live performance at one of the town’s legendary music venues. Indulge in farm-to-table cuisine at local eateries, sample craft brews at cozy pubs, or immerse yourself in the town’s thriving arts community.

With its proximity to breathtaking natural landscapes and an array of outdoor activities, including hiking, biking, and wildlife spotting, Woodstock offers the ideal getaway for urban dwellers craving a taste of rustic charm and outdoor adventure.

Best Hikes Near Woodstock

Whether you’re seeking a leisurely stroll or a thrilling mountain ascent, these best hikes near Woodstock NY promise unforgettable experiences amidst the stunning beauty of the Catskills.

Get ready to embark on a nature-filled adventure with the best hiking trails near Woodstock!

Sloan Gorge Preserve

One of my favorite short hikes is Sloan Gorge Preserve, which is lovely at any time of year. It’s a super-short but super-fun hike through an impressive bluestone quarry that descends into a dramatic rocky gorge with imposing cliffs and a wonderful rock-passage to climb through called The Chimney.

best hikes near woodstock ny: forest cliff face
Wear red in nature, you’ll look awesome.
teenager in gorge rock face
The Chimney at Sloan Gorge

We did it counterclockwise for this trail guide, but it’s best to do it clockwise. That is, turn left at the first junction and do the short quarry loop first. Then head down into the gorge itself.

Israel Wittman Sanctuary

Israel Wittman Sanctuary is a lovely woodsy nature walk that not many people know about. Beautiful, contemplative mixed forest, easy stream crossings, delightful footbridges, quiet ponds and pools, and small field of glacial boulders.

trail through woods
White pine and hemlock

best hikes near woodstock ny: Israel Wittman pine trees
The Tall Pines in winter

There are now three loops, A, B, and C. All are easy to do. A & B both pass along either side of a gorge with some nice rock drama on both banks. Loop C passes through some old quarries.

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Ashokan Rail Trail

While not technically a hike, the Ashokan Rail Trail is one of the premier destinations in The Catskills.

Ashokan Rail Trail wooden bench beside reservoir with mountain views
Bench and views

Built with accessibility in mind, this wide, straight and almost perfectly flat walking trail is 11.5 miles long, with multiple parking lots along its length. Perfect for a short stroll or a long bike ride. This is one of the most beloved hiking trails near Woodstock, NY.

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The Comeau Property

Consider also the Comeau Property in Woodstock itself, an easy, woodsy loop that passes by a stream. It’s a little nature oasis right in town.

Snake Rocks Preserve

Snake Rocks Preserve is short, strange hike that leads through one of the largest and most impressive bluestone quarries in The Catskills.

Quarry pond

The massive, abandoned bluestone quarry dates from the late 1800’s. It supplied Catskills bluestone for some of New York City’s most famous buildings. The piles of quarry tailings are really something, as are the views from on top of them. There’s even some fish in a very striking quarry pond!

Ticetonyk Mountain

I figured Ticetonyk was beautifully positioned to have great views — but I had no idea. Ticetonyk’s lookouts are now among my favorites in The Catskills.

One of the Best Hikes Near Woodstock: Ticetonyk
View from Ticetonyk Mountain, one of the best hikes near Woodstock

This is the perfect short mountain hike: under 3 miles, with about 900 feet of elevation gain. It’s a great little huffer that doesn’t take all day. And the view from the lookout is one of the great Catskills views.

I hike this trail several times a month. It really is one of the best hikes near Woodstock, NY.

And finally…

Overlook Mountain Ruins & Fire Tower

If you want something a little more strenuous (but not killer hard) there’s always the classic hike to Overlook Mountain Fire Tower. This is one of the most popular  hikes in The Catskills, and you’ll definitely agree it’s one of the best hikes near Woodstock, NY.

best hikes near woodstock ny: Overlook fire tower
Overlook Mountain Fire Tower is 60 ft tall

It’s a very straightforward uphill walk that packs a punch at the top with massive hotel ruins and one of the best views in the Catskills Park.

Overlook Hotel ruins

catskills sunrise/sunset view
Pre-dawn light over Indian Head, Kaaterskill High Peak and the Blackhead range, seen from Overlook Fire Tower

Overlook Fire Tower is also an amazing location for a your first sunrise hike.

You will cherish the memories of these scenic trails, each of which offers a unique adventure. These are the best hikes in Woodstock, NY, promising unforgettable outdoor experiences. Happy hiking!

Similar Hikes to the Best Hikes Near Woodstock

Here are some of the easiest hikes and most scenic trails in the area.

And these trails are all kid-friendly.

Read More

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