Fun Things to Do in Woodstock, NY 2023

The charming town of Woodstock is home to several unique attractions and activities that draw visitors from all over the world. If you’re planning on visiting this Upstate New York gem any time soon, we recommend checking out this list of the top things to do in Woodstock, NY. These activities, sights and experiences will help you make the most of your time in this wonderful village nestled in the eastern portion of the Catskills.

See a Show at The Woodstock Playhouse

The Woodstock Playhouse is a professional theater that has been delighting audiences for years. The theater features a wide variety of productions and is home to a troupe of talented actors, producers, and crew members who put on several shows each year.

Woodstock Playhouse, Bryce Gruber

The theater is located in a beautiful building that was built in the early 1900s. We recommend attending one of the theater’s shows, as it is a great way to explore the local arts and culture while also having a fun night out with friends and family. If you are planning to attend a performance, we recommend

Walk the Ashokan Rail Trail

If you’re looking for free things to do in Woodstock, NY that leave a lasting impression, a visit to the Ashokan Rail Trail is a sure winner. The 11.5-mile recreational trail runs along Ashokan Reservoir between West Hurley and Boiceville, NY. While it’s not Woodstock, per se, West Hurley is the neighboring town and even overlaps some zip codes.

The Ashokan Rail Trail is a comfortable 12-foot width so there’s plenty of room to walk with friends, go for a solo bike ride or take pups along. Both the trail itself and trailhead parking areas are ADA-compliant and accessible for those with disabilities. Pets must be leashed at all times. The views are breathtaking, and it’s completely free.

Ashokan Rail Trail, Bryce Gruber

It’s important to know that the trail is never plowed though, so if you’re looking to make this a wintertime activity in Woodstock, NY—bring snowshoes or cross-country skis. The parking lot and road to the trail itself is plowed, though.

Have Coffee at The Mud Club

Want to hang out with a good cup of coffee in the center of Woodstock? Visit The Mud Club, an enchanting set up right on Tinker Street. It’s an ideal place to set up with a cozy drink, read a book or just spend an afternoon people watching.

The Mud Club in Woodstock, @themudclubwoodstock

At night, the scene transforms into a cool and very vibey bar scene. Go here for sunset drinks, a romantic outing and hanging with friends. It’s the polar opposite of the cheap alcohol and sports you’d get a pub though, so don’t expect that.

Watch A Movie at the Woodstock Film Festival Showing Theater

The Woodstock Film Festival is an annual event that celebrates the art of cinema through screenings of short and feature-length films. The festival is held over a weekend in late October at various locations across the village, including this beautiful theater. The theater was originally built in 1926 and is one of the oldest operating theaters in the United States. Visitors can watch modern and classic films, learn about the history of cinema, and explore the theater’s architecture and design at various events and exhibitions held during the festival. The festival also includes a special event called “The Big Screen” that allows guests to watch a classic film by the fireplace inside the theater.

Have a bite at Bread Alone Bakery

If you’re meandering through town or looking for a snack after hitting up The Mud Club, venture over to Bread Alone Bakery. It’s just across Tinker Street. Grabbing a pastry at this iconic shop one of the most popular things to do in Woodstock.

Bread Alone Bakery on Tinker Street in Woodstock, @breadalonebakery

They’re a community staple with treats worthy of big city lines. In fact, they’ve gotten so popular that locations are opening all over the Hudson Valley. If you’re in the mood for a drive, you can also check out the new Boiceville Bread Alone location. Pick up some bread, muffins, and croissants—you won’t regret it.

Love this article? If you think it’s super great, sign up for the Extra Good newsletter. You’ll get weekly must-know info and generally titillating updates.