5 Best Hiking Trails Near Woodstock

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Ashokan Rail Trail scenic water view

Eastern scenic spot

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Searching for the best hiking trails in Woodstock, New York? This post has you covered.

These are the five easiest hikes in the Woodstock area. These trails are kid-friendly so the whole family can enjoy a deep nature excursion that includes easy walking, amazing scenic views, and even some of The Catskills’ most impressive historic ruins.

Enjoy the best hiking trails near Woodstock…

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forest cliff face
Wear red in nature, you’ll look awesome.

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.

I 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.

catskill sactuary
Delightful forest walk

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.

There are two loops, A and B. Both are easy to do and both pass along either side of a stream with some nice rock drama on both banks.

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

Ashokan Rail Trail

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

The Comeau Property

Consider also the Comeau Property right in Woodstock itself. I haven’t been there recently but, from memory, it’s an easy, short loop walk that passes by a stream.


knoll and mountain from indian head
Indian Head’s “chin” and Overlook Mtn seen at sunset from Indian Head’s “nose“

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.

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.

It’s also an amazing location for a your first sunrise hike.

These are the five best hiking trails near Woodstock, New York.

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

These trails are all kid-friendly.

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