5 Best Hiking Trails Near Woodstock

Ashokan Rail Trail scenic water view

Eastern scenic spot

Similar Entries In: Home Page, Nature Trails, Recommended Reads, The Best Hikes, The Easy Hikes, The Most Popular Hikes, , , , , , .

Disclosure: Links to external websites on this page may be affiliate links. As an Amazon Associate I earn from qualifying purchases. This means, at no additional cost to you, I will earn a commission if you click through and make a purchase.

Searching for the best hiking trails in Woodstock, New York?

Here are the easiest hikes and most scenic trails in the Woodstock area. These trail are all kid-friendly so the whole family can enjoy a nature excursion with easy walking, amazing views and even some of The Catskills most impressive historic ruins. Enjoy these hiking trails near Woodstock.

This post is free to all readers thanks to my Patreon subscribers who kindly support this content

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

1. 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.

BTW, winter is coming — time to pick up a set of the best microspikes you can buy

catskill sactuary
Delightful forest walk

2. 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

3. 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.

4. 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.

Finally…

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

5. 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.

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

Read More

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

These trails are all kid-friendly.

Follow for More

Follow my @TotalCatskills account on Instagram for regular hiking inspo and safe, inclusive community.

I also stay active on Facebook and Twitter.

Hot on the website right now…

Open for Later

You too can support this independent hiking content and get great benefits!

Support independent hiking content and enjoy excellent patron-only benefits

Your comments are welcome here…

Hello, I’m Sean

I write independent hiking content to help hikers like you find amazing hikes in the Catskills, Adirondacks, Gunks, Hudson Highlands, Taconics and beyond.

On social media, I’m @TotalCatskills. Follow me on Facebook, Twitter, YouTube and Instagram.

My free weekly hiking newsletter is low key awesome.

You won’t regret signing up…