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You're never far from the magic when you step into Sean Doolan's parlor for Magic on Main.

Best Things To Do near Windham Mountain with Kids

1. Magic on Main

Magic on Main is an intimate parlor experience. Magician Sean Doolan invites you into his home for a one-of-a-kind magic show, which takes place in his private library that only holds 10 people. If you like to laugh while watching sensational magic tricks, then Magic on Main is for you. The show is very engaging and will leave the whole family wondering “how did he do that?!”

2. Windham Mountain

This family-friendly mountain resort offers tons of fun all year long. Although most famous for its 54 trails on 285 skiable acres, Windham Mountain packs in a ton of snowless fun with its mountain bike park, festivals, and family-fun events in the summer, spring, and fall, too.

Winter at Windham Mountain means skiing, tubing, skating—and even kids’ snowmobiling! The mountain has a great learn-to-ski program for beginners through advanced levele skiers.

3. Five State Lookout

This spot’s name is an appropriate description of the view. On a clear day you can see the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshires Mountains of Massachusetts, the Helderberg Mountains of New York, and the Connecticut Valley.

4. The Windham Path

The Windham Path is a family-friendly, public, 1 1/2-mile looping trail. In the summer, the path is home to bikers, walkers, and runners, while in the winter you can find cross-country skiers or snowshoers utilizing this popular trail.

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Enjoy a scenic horseback ride through the rolling mountain landscape courtesy of Mountain Brook Farm. Photo courtesy of the farm

5. Mountain Brook Farm

From farm experiences to pony rides to trail rides through the Northern Catskill Mountains, Mountain Brook Farm has been providing equestrian experiences for over a century. Ride through beautiful mountain views while learning the basics of horseback riding.

6. Briars and Brambles Books

Briars and Brambles is the “go-to Indie Bookstore in the heart of the Catskill Mountains.” This cozy little bookshop is stocked with vacation reads, classics, a phenomenal YA section, and a lovely little book nook for the littlest readers.

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A mouthwatering beef stew is a must-order comfort classic when dining at Babblers.

Best Restaurants for Families near Windham Mountain

7. Babblers Restaurant and Bakery

Located in the Wylder Windham, Babblers Bakery is open for breakfast and light bites, plus grab-and-go bites throughout the day. It offers coffee, fresh croissants, soft-serve ice cream, and a selection of pastries. Babblers Restaurant is the perfect place to end the day. Its laid-back vibe feels like you are eating at home—minus the cooking.

8. Catskill Mountain Country Store

Is it a store? Is it a restaurant? A playground? A petting zoo? It’s all of the above! The Catskill Mountain Country Store offers plenty of entertainment while waiting for your table. The restaurant is open for breakfast and lunch daily.

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Higher Grounds waffles are worth traveling for.

9. Higher Grounds

Higher Grounds is open for breakfast and lunch daily. Don’t let its name fool you—this spot serves much more than coffee. Smoothies, hot cocoa, salads, omelets, pastries, and sandwiches make Higher Grounds a perfect stop any time of the day. Pro tip: Order the waffle. You won’t be sorry.

10. The Windham Local

The Windham Local serves breakfast, lunch, and dinner, with a menu packed with comfort foods like breakfast sandwiches, grilled cheese, and tomato soup, as well as Thai classics like curry and pad thai for more adventurous eaters.

11. Tavern 23

A traditional tavern menu hits the spot after a day on the mountain. Dine on roast chicken, steak-frites, seafood, pasta, and weekly prime rib specials. Make sure to save room for the chocolate fondue, a family favorite!

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The family-friendly Wylder Windham has a variety of rooms, suites, and cottages to make you comfortable no matter your family's size.

Where to Stay near Windham Mountain with Kids

12. Wylder Windham

Wylder Windham is a quick five-minute drive from Windham Mountain, making it an ideal spot to call home while in town. This property boasts 110 rooms spread across 20 acres of land located alongside the Batavia Kill River. Whether you choose to stay at the property’s Pines Inn, Tamarack Lodge, Manor, Spruce Cottage, Evergreen Lodge, Main Lodge, or Farmhouse, your family is sure to have a great time. No car? No problem! You can hop in the restored vintage Land Rover Defender 110 Shuttle that provides complimentary guest transportation to Windham Mountain, Windham Country Club, and downtown Windham. While it won't pick you up from the train station in nearby Hudson, a car service can drop you off at the hotel's doorstep.

Wylder Windham is stocked with tons of year-round, family-friendly amenities. An expansive outdoor lawn with pickleball courts, hammocks, tree swings, fire pits, lawn games, and live entertainment provides hours of entertainment in the warmer months. There is also a heated outdoor pool that is typically open from May-October.

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Play old-school games at Wylder Windham's rec room during your downtime.

In the basement of the main building, a nostalgic recreation room with pool tables, shuffleboard, vintage arcade games, foosball, and more is available for everyone to use. This cozy spot is perfect for larger group get togethers or just hanging out with the family. Wylder Windham also has a rotating schedule of organized events on the property that range from movie nights and s'mores parties to karaoke nights, snow tubing, and more.

One of our favorite amenities was the two wood-fired saunas. After a day spent adventuring in the cold, we loved warming up in one of these private saunas. They are the perfect spot for two or three people to relax while taking in the pristine mountain scenery.

Unless noted, photo by the author