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A word to the wise: While Woodstock, New York, is a great all-season destination, it caters to the weekend crowd. Many of the small businesses are closed mid-week, so be sure to check hours before heading out!

Best Things To Do in Woodstock, NY, with Kids

1. Tinker Street

Woodstock's main street, Tinker Street is filled with cute and creative shops, family-friendly eats, and plenty of treasures to unearth as you wander in and out of its small businesses. It's truly the heartbeat of this Ulster County town.

2. Woodstock Public Library

Founded by curious townspeople more than 100 years ago, the Woodstock Public Library maintains its mission to serve the community through free and open access to information. Beyond lending, it offers an eclectic event calendar catering to all ages in the community.

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Woodstock Waterfall Park is located just off of Woodstock's main drag, Tinker Street. Photo by Ajay Suresh via Flickr 

3. Woodstock Waterfall Park

This small but mighty green space is located just off Woodstock's main drag and paints a picturesque scene with beautiful waterfalls cascading on the lovely Tannery Brook.

4. Woodstock Farm Festival

Celebrate local eats, live music, and the community at this weekly festival highlighting local vendors and talent on Wednesdays from mid-May through early October.

5. The Golden Notebook

This independent bookstore has been a mainstay on main street since its opening in 1978. A well-stocked kids section, Little Golden, is a welcoming sight on the second floor and a jam-packed events calendar offers a real sense of community.

6. Candlestock

Step inside the downtown location of this local candle shop to see its Drip Mountain, a glowing waxy masterpiece that's been wowing visitors since '69. Stock up on supplies—Hippy Drippy Candles—to start your own wax installation or enjoy weekend candle-making classes at its Saugerties location.

7. Overlook Bicycles

If you're looking to take advantage of the beautiful scenery surrounding town, consider renting a bicycle at Overlook Bicycles, which even has kids' sizes!

8. Comeau Property

Convenient to the town center, this sprawling green space offers 76 acres of woods, meadows, and a tranquil walking path along the Sawkill Stream. Kids love clambering up the rocks as you explore! In winter, it's a perfect backdrop for a sledding adventure.

9. Ashokan Rail Trail

Explore the northern rim of the Ashokan Reservoir on this rail trail, which sits on the old Ulster and Delaware Railroad property. Running 11 1/2 miles long, it's great for strolling, biking, and even cross-country skiing in the winter! Fishing is allowed in the reservoir and it's an excellent spot to search for bald eagles.

Top Attractions in Woodstock, NY, with Kids

10. Woodstock Playhouse

Founded in 1938, the not-for-profit Woodstock Playhouse hosts a wide variety of live entertainment from theater to music, dance, visual arts, and more. See what's playing when you visit!

11. Overlook Mountain

For a walk on the wild side, explore the trails of Overlook Mountain, where you can find a historic fire tower, mountain house ruins, and panoramic views of the Hudson River Valley during a 5-mile hike. Exploring with little ones? Try the lower-lying Overloop Trail instead.

12. Opus 40

Explore more than 60 acres of walkable trails, a gallery, a museum, and sitting areas at Opus 40 in nearby Saugerties. It's one of our favorite destinations for an outdoor art day trip!

RELATED: 3 Days in the Hudson Valley with Kids: Ultimate Itinerary by a Local Mom

Visit the Karma Triyana Dharmachakra Tibetan Buddhist Monastery on a trip to Woodstock. Photo by Patrickwooldridge, CC0, via Wikimedia Commons

13. Karma Triyana Dharmachakra Tibetan Buddhist Monastery

Explore the grounds, gardens, and temple at the scenic Karma Triyana Dharmachakra Tibetan Buddhist Monastery. Guided tours are offered on weekend afternoons, though guests are welcome daily from sunrise to sunset.

14. Mount Tremper

Another of the Catskills peaks, Mount Tremper offers miles of trails culminating in a spectacular view from the fire watchtower atop the peak. Visitors enjoy birding along the way and off-season snowshoeing is a popular activity.

Best Restaurants for Kids in Woodstock, NY

16. Harley's Sweet Spot

Ice cream, candy, and cold drinks call out to visitors from Harley's Sweet Spot. This new-to-town confectionery is named for the proprietor's first-grade son.

17. Woodstock Brewing

Head to this local brewery for small-batch selections in a laid-back atmosphere. A lovely backyard beckons families and there are plenty of kid-friendly eats on its menu. Let the kids nosh on a homemade Crumbl Cookie while you sip another pint.

18. Peace, Love and Cupcakes

Baker Janice Hardgrove-Kollar is a self-professed baking addict and her creative combinations at Peace, Love & Cupcakes won over locals long before they landed her on the Food Network where they won over the judges—twice.

19. The Mud Club

Wood-fired bagels and organic coffee are the claim to fame at The Mud Club. Later in the day, it switches the menu and offers sourdough pizza!

20. Bread Alone

A mainstay at regional farmers markets, why not head to the source at the Woodstock cafe from Bread Alone? It serves three meals a day, seven days a week from its central Mill Hill Road location.

21. Oriole 9

Situated on Tinker Street, Oriole 9 serves comfort food classics from an unassuming cafe. There are enough options here that even the most picky eaters are pleased.

22. Overlook Bakery

You can't leave town without a stop at Overlook Bakery for a freshly baked salty chocolate chunk cookie!

Where to Stay in Woodstock, NY, with Kids

23. AutoCamp Catskills

Give the unique accommodations at AutoCamp Catskills a try. You can choose to stay in an Airstream, Family Cabin, or a glamping tent. No matter what you choose, there are plenty of resort-style amenities to enjoy on the property!

24. Emerson Resort and Spa

Guests at this Mount Tremper resort can stay in either the Lodge or the Inn—though the Lodge, which features a family suite that can sleep up to six, is a good choice for larger groups.

25. Hotel Dylan

The boutique Hotel Dylan is as eclectic as the town it calls home. Families can appreciate the board games for loan, the sprawling common lawn with fire pits, and a seasonal saltwater pool. 

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