20 Best & Fun Things To Do In Windham, NY

Are you a resident or tourist looking for fun activities in Windham, New York?  Look no further! You’re in the right place.  In this guide, we’ll unveil an extensive list of the 20 best and most fun things to do in Windham, NY, to make the most of your time in this picturesque Greene County.

Windham, New York, is a charming town nestled amidst the scenic Catskill Mountains. Renowned as the “Gem of the Catskills,”  it boasts a rich history, breathtaking natural beauty, and a plethora of recreational activities for all seasons.

Windham is a haven for skiers and snowboarders in the winter. The resort transforms into a paradise for mountain bikers and hikers during the warmer months, offering scenic trails and challenging terrain.

As one of the fastest-growing cities in Greene County, New York, this charming city provides numerous fun, entertaining, and educational opportunities from the Windham Mountain Resort, ensuring everyone can create an exciting memory during their stay in Windham.

20 Best And Fun Things To Do In Windham, NY (2024)

1. Windham Mountain Resort

Nestled in the heart of New York’s Catskill Mountains, Windham Mountain Resort is a year-round destination that caters to outdoor enthusiasts and those seeking a scenic getaway.

With 54 trails across varied terrain and a vertical drop of over 1,600 feet, Windham Mountain caters to skiers and snowboarders of all levels. Whether you’re carving fresh powder or cruising down gentle slopes, the resort offers an exhilarating experience.

For mountain biking enthusiasts, Windham Mountain Bike Park boasts over 50 miles of trails designed for all skill levels. From thrilling downhill courses to scenic cross-country routes, the park caters to every rider’s preference.

Windham Mountain Resort offers other exciting activities, such as golfing, and night skiing. This resort offers a variety of lodging options to suit your needs, from slopeside hotels and condos for easy access to the action to cozy cabins perfect for a more rustic retreat.

2. The Windham Path

The Windham Path is a perfect choice if you’re looking for a relaxing and scenic walk or bike ride in Windham, NY. The Windham Path is a great option for a family outing, as it’s an easy and relatively flat trail.

The Windham Path consists of two loops: a 1.5-mile loop and a 0.5-mile loop that connects the business area of South Street and Route 296. You can choose to do one loop or combine them for a longer walk or ride.

Bring your furry friend along for a walk, keeping them leashed for everyone’s safety. The path is mostly flat and well-maintained, making it suitable for visitors of all ages and abilities.

Address: 4982 NY-23, Windham, NY 12496, United States.

3. Five-State Lookout

Immerse yourself in nature’s beauty by exploring the Five-State Lookout with your friends. On a clear day, the lookout offers stunning panoramic views encompassing five states: New York, Vermont, Massachusetts, Connecticut, and New Hampshire.

Five-State Lookout is a basic area for observation, with a parking lot and minimal facilities. This lookout is likely most enjoyable during clear weather conditions, especially in the fall when the foliage bursts with vibrant colors.

You might consider visiting the Five-State Lookout alongside other nearby attractions like hiking trails, historical sites, or charming towns in the area. On your visit to Windham, be sure to stop by Acra and explore the Five-State Lookout in New York.

Address: 7604 NY-23, Acra, NY, 12405, United States.

4. Escarpment Trail

The Escarpment Trail is a challenging yet rewarding hike located in the Catskill Mountains near Windham, New York. This park offers stunning views of the surrounding mountains and countryside, making it a popular destination for experienced hikers.

The Escarpment Trail is considered a challenging hike, with a total elevation gain of over 3,000 feet. The trail is mostly narrow and rocky, with some steep sections. Hikers should be in good physical condition and have experience hiking challenging trails.

Hikers can choose to hike a shorter section of the trail out and back, turning around at any point. A popular option is to hike to the summit of Blackhead Mountain, which is about 6.7 miles round-trip from the Windham Trailhead.

Address: 3 Cross Road, Windham, NY 12439, United States. ( Windham, entrance)

5.  Main Street Community Center

One of the most interesting places to visit in Windham is the Main Street Community Center. This must-see attraction is a valuable resource for the community, offering a variety of programs and services.

This center functions as a hub for the Windham community, offering programs, events, and resources for people of all ages. This center is focused on building a welcoming and inclusive space for everyone in the community.

Main Street Community Center offers a variety of programs, including after-school activities for children, classes and workshops for adults, fitness programs, support groups, and community events.

Address: 5494 NY-23, Windham, NY, 12496, United States.

6. Windham Fine Arts

Windham Fine Arts is a contemporary art gallery located in the heart of the Catskills Mountains at the base of Windham Mountain Resort. They’ve been established for over 20 years and represent a diverse range of artists.

Windham Fine Arts showcases contemporary art, featuring a variety of styles and mediums.  Expect to find paintings, photography, sculptures, mixed media pieces, and more, catering to a variety of tastes.

Furthermore, this gallery represents both local and internationally acclaimed artists, offering a well-rounded perspective on the contemporary art scene.

Address: 5638 Route 23, Windham, NY, 12496, United States.

7. The Vineyard at Windham

Make a toss with a variety of New York’s finest wines at The Vineyard at Windham with your friends in Windham, NY. Nestled in the Castle Mountains, The Vineyard at Windham provides a stunning, view-enhancing experience.

This wine spot celebrates New York State viticulture by offering a selection of wines produced from grapes grown in various regions across the state, including the Finger Lakes, Hudson Valley, North Fork, and South Fork of Long Island.

The Vineyard at Windham offers a charming and inviting atmosphere, perfect for relaxing and savoring the wines. Vineyard staff are knowledgeable and passionate about wines, offering guidance and recommendations as you explore the selection.

Address: 11 Mount View Estates Road, Windham, NY 12496, United States.

8. Bailiwick Animal Park & Riding Stables

Exploring Bailiwick Animal Park & Riding Stables is one of the most fun things animal lovers can do near Windham, NY. This family-friendly park offers a fun combination of animal encounters and horseback riding experiences.

Bailiwick Animal Park features a small zoo with a mix of exotic and farm animals, including sheep, pigs, llamas, bears, alligators, tigers, and more. This park provides a designated petting area where you can interact with friendly animals.

What’s more,  Bailiwick Animal Park & Riding Stables offers horseback riding lessons and trail rides for all experience levels, from beginners to experienced riders. For younger visitors, pony rides are available for a fun and safe introduction to horseback riding.

Address: 118 Castle Road, Catskill, NY, 12414, United States.

Are you exploring other attractions in New York? Why not check out some fun things to do in Woodstock and fun things to do in Ellicottville?  

9. European Craft Store

Are you interested in unique and handcrafted products? If yes, then venturing into the European Craft Store is one of the most interesting things to do in Windham, NY.

The European Craft Store specializes in handmade items with a European influence, offering a distinct selection compared to generic craft stores. Expect to find an array of products, including amber jewelry, Polish pottery, wood carvings, chess sets, nesting dolls, and more.

This craft mall sources its products from local artisans or workshops, promoting handcrafted goods and supporting the community.  The store is described as having a warm and welcoming atmosphere, making it a pleasant place to browse and shop.

Address: 11111 State Route 23, Windham, NY, 12496, United States.  88

10. Windham Public Library

For book lovers, exploring the Windham Public Library is one of the most exciting things to do in Windham, NY. This library functions as a community hub, offering a welcoming space to read, relax, attend events, or connect with others.

You can borrow a wide selection of books, audiobooks, ebooks, DVDs, and other materials for all ages and interests. This book establishment hosts various events like author talks, book clubs, story times for children, or educational workshops.

One exciting fact about Windham Public Library is that it provides public computers with internet access for browsing, research, or using digital resources.

Address: 5379 NY-23, Windham, NY, 12496, United States.

11. Magic On Main

Create an exciting relationship bond with your partner by exploring a magic show in Windham, NY. Magic on Main. An intimate parlor magic show experience hosted by magician Sean Doolan.

This magic show takes place in Sean Doolan’s private library, creating a close-up and intimate setting for the audience. Get inspired as Sean weaves his personal story of transitioning from a trial lawyer to a magician into the performance, making it interactive and engaging.

Expect to be amazed by Sean’s skilled sleight of hand and illusions that will leave you questioning reality.  Due to the intimate setting, seating is limited to only 10 people per show.

Address: 5428 NY-23, Windham, NY, 12496, United States.

12. Christman’s Windham House

Established in 1805, exploring Christman’s Windham House is one of the most interesting things to do in Windham, NY, for tourists. Christman’s Windham is a historic landmark offering a unique blend of accommodation, dining, and recreational activities.

Christman’s Windham House’s architectural style and ambiance reflect a colonial-era style, offering a charming and historic atmosphere. This historic accommodation offers a variety of room options to suit different needs, from cozy guest rooms to spacious suites or efficiencies.

This property features an on-site restaurant where you can enjoy delicious meals without having to venture out, as well as a bar or lounge area for drinks and socializing. Christman’s Windham House provides amenities such as golf courses, an outdoor pool, a tennis court, and a game room.

Address: 5742 Main Street, Windham, NY, 12496, United States.

13. Millrock Restaurant & Bar Room

The Millrock Restaurant & Bar Room in Windham, NY, is a delightful spot to enjoy a delicious Italian meal and drinks with your friends in the cool of the evening.

Millrock Restaurant & Bar Room specializes in classic Italian dishes like pasta, pizza, and fresh seafood.  Their menu offers generous portions, ensuring you leave satisfied.

The dining room is described as having a warm and inviting atmosphere, perfect for a relaxed and enjoyable dining experience. This restaurant provides scenic views of Windham Mountain while you savor your meal.

In addition, have a romantic time with your partner on the Millrock Restaurant & Bar Room deck and enjoy the fresh mountain air, especially during pleasant weather. They also feature live music performances on their deck or patio on weekends during peak season, making it one of the most romantic things to do in Windham.

Address: 5398 NY-23, Windham, NY, 12496, United States.

14. Windham Theatre and Vacation Rentals

The Windham Theatre and Vacation Rentals is an accommodation provider. They specialize in renting out luxurious vacation homes in the Windham area.

Windham Theatre and Vacation Rentals offers a variety of rental properties, ranging from cozy cabins to spacious houses, catering to different group sizes and preferences

in addition, Windham Theatre and Vacation Rentals could include amenities such as hot tubs, saunas, decks, fireplaces, or other features to enhance your stay.

Address: 11 Vets Road, Windham, NY, 12496, United States.

15. The Knitting Room, NY

For yarn enthusiasts, exploring the Knitting Room in Windham, New York, is one of the best places to purchase creative products. Overall, The Knitting Room is more than just a store, it’s a community hub for crafters.

The Knitting Room, NY, prioritizes sourcing high-quality yarns and crafting supplies. They specifically seek products made with sustainable practices and ethical treatment.

This creative store offers a curated selection of yarns, ensuring you find the perfect type and color for your project. You’ll likely find other crafting supplies like needles, hooks, buttons, and notions. With a warm and inviting environment, it makes a great place to browse their selection, get inspired for new projects, and connect with other fiber artists.

Address: 11111 State Route 23, Windham, NY, 12496, United States.

16. New York Zipline Canopy Tours

New York Zipline Canopy Tours, also known as Hunter Mountain Zipline, is an exciting adventure outfitter located in Hunter Mountain, New York.

This park offers exhilarating zipline tours through the breathtaking Hunter Mountain forests, allowing you to experience the beauty of the Catskills from a unique perspective.

New York Zipline Canopy Tours features a Skyride tour, where you can test your climbing skills. Soar through the mountain air on a series of interconnected ziplines, reaching speeds of up to 50 mph and offering stunning panoramic views from nearly 600 feet above the ground.

What’s more, this is a family-friendly option with a series of six ziplines and four rope bridges, providing a fun and scenic adventure through the forest canopy. Challenge yourself on this four-story climbing tower, featuring various obstacles to test your skills and bravery.

Address: 64 Klein Avenue, Hunter, NY, 12442, United States.

Are you exploring other attractions in New York? Why not check out some fun things to do in Queensbury? 

17. Launch Trampoline Park

Positioned in Queens, Launch Trampoline Park is a fun destination for an energetic family outing. This park features a wall-to-wall trampoline, which offers a vast space for bouncing for all ages.

Launch Trampoline Park offers dodgeball courts with trampolines that add a new twist to the classic game, perfect for friendly competition,, as well as a ninja warrior course and a climbing wall that puts your climbing skills to the test.

Launch provides party rooms for hosting birthday parties or other celebrations. An arcade with redemption games can provide additional entertainment for visitors. This park also features an on-site cafe, where you can grab refreshments and snacks to refuel after all the bouncing fun.

Address: 163-50 Cross Bay Blvd., Queens, NY, 11414, United States.

18. Windham Country Club

Exploring Windham Country Club is one of the most fun things to do in Windham, NY, with your friends today. Nestled amidst the scenic Catskill Mountains, this golf course offers an exceptional golfing experience for players of all skill levels.

This beautifully positioned 18-hole and 72-par championship course provides a blend of challenge and playability, making it enjoyable for golfers of various skill levels. Expect beautiful greens, fairways, and stunning mountain views that enhance the golfing experience.

Windham Country Club features a driving range where you can practice and warm up your swing at the grass driving range before hitting the course.

Beyond the excitement of golfing, this gold course features a clubhouse that offers a pro shop, a banquet facility, and a restaurant where you can enjoy a delicious meal or refreshing beverage before or after your round.

Address: One Country Club Road, Windham, NH, 03087, United States.

19. Windham Farmers’ Market

Situated on Windham’s main street, across from the Windham Local Public House, exploring the Windham farmer’s market is one of the best things to do in Windham, NY, on the weekend.

The Windham Farmers’ Market offers a wide selection of fresh, high-quality produce and goods directly from local farmers and artisans. This market focuses on seasonal products, such as fruits and vegetables, herbs, cheeses, honey, maple syrup, baked goods, meat, eggs, and well-crated local artifacts.

In addition, this market provides an opportunity to support local farmers and businesses, as well as create a vibrant community space where people can connect.

Address: Main Street in Windham, NY, United States.

20. Ze Windham Wine Bar

Wine Bar is a charming wine bar situated in Windham, New York. It boasts a genteel atmosphere within a converted old house and offers a delightful patio for enjoying drinks outdoors

Ze Windham Wine Bar’s main attraction is the wine and cheese pairings. This wine establishment offers nearly 40 wines by the glass, allowing you to explore a variety of options. They also offer beer and cider options, catering to a wider range of preferences beyond wine.

This exciting outdoor spot provides a menu offering a selection of small plates with a focus on German and Swedish culinary influences. This can be a great way to sample different flavors and share them with friends.

Address: 5369 Main Street, Windham, NY, 12496, United States.

Plan Your Trip To Windham, NY