12 Best Things To Do In Windham, New York - Updated 2022

things to do in windham new york

Those who enjoy spending their days off outside need to consider places that have both active and relaxing things to do in order to have a fun and memorable weekend. If you and your friends fit in this group, then you should put visiting Windham, New York on your to-do list for your next long weekend. There are plenty of trails on mountains to choose from in case you’re in the mood for a hike, as well as easy trails perfect for just a walk. There are plenty of shops and establishments you can check out along the way for commercial purposes too. To make the most of your vacation in Windham, stay in one of the Airbnb vacation rentals available. Consider these best things to do in Windham, New York, the next time you’re planning your weekend.

1. Magic On Main

Editor's Note: Photo taken from the establishment's official social account

Posted by Magic On Main on Sunday, December 12, 2021

For a magical experience with the whole family, check out Magic On Main. It is definitely not your usual magic show as it’s going to be in magician Sean Doolan’s private library, providing you with an intimate and interactive magical experience. More than the magic tricks and sleights of hand, get the first-hand account of how and why Sean Doolan transitioned from a trial lawyer to a great magician who fully dedicates his life to this ancient art form.

Magic On Main

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

Website: Magic On Main

2. Windham Theatre

Editor's Note: There's no photo available at the time of writing

Windham Theatre is a cinema complex that shows all the latest films, making it one of the local favorite go-to places for those looking to have a great time at the movies. This clean and well-maintained cinema complex features cozy seats and a concessionaire that offers a wide array of tasty snacks and refreshing drinks.

Aside from the movies, this place also offers other fun activities as it has a minigolf course, an arcade, and more—truly a one-stop shop to enjoy bonding with your whole family.

Windham Theatre

Address: 11 Vets Rd, Windham, NY 12496, United States

Website: Windham Theatre

3. Ze Wine Bar

Editor's Note: Photo taken from the establishment's official social account

Sample some of the best tasting wines in the region by visiting Ze Wine Bar. Boasting an extensive wine list, the bar carries some of the best wines that come from around the world including whites and roses like chardonnay, moscato, and Provencal rose. You can also enjoy different reds and sparkling cocktails such as pinot noir, super Tuscan, and sparkling Swedish elixirs. To go with these top-notch drinks, you also get to enjoy light bites and charcuterie board options.

Ze Wine Bar

Address: 5369 Main Street Behind the Post Office, Windham, NY 12496, United States

Website: Ze Wine Bar

Opening hours: Fri: 2pm - 8pm; Sat: 12pm - 8pm (closed on Sun, Mon, Tue, Wed, & Thu)

4. Bistro Brie & Bordeaux

Editor's Note: Photo taken from the establishment's official social account

To complement your vacation in the mountaintop town of Windham, enjoy a French cuisine dinner at Bistro Brie & Bordeaux. With this French bistro’s simple yet charming setting with artworks, flower-lined porch, soft jazz music, and magnificent view of the mountains, it’ll be like the cherry on top of your wonderful Windham vacation.

The food is remarkable as well—from escargots and charcuterie boards to seafood pasta and slow-braised beef short ribs in a cabernet sauce, you’ll certainly never go wrong. Of course, a French meal wouldn’t be complete without a fine bottle of wine and Bistro Brie & Bordeaux has an extensive wine list to choose from.

Bistro Brie & Bordeaux

Address: 5386 NY-23, Windham, NY 12496, United States

Website: Bistro Brie & Bordeaux

Opening hours: Fri - Sun: 5pm - 8pm (closed on Mon, Tue, Wed, & Thu)

5. Windham Mountain Adventure Park

Editor's Note: Photo taken from the establishment's official social account

It’s difficult to find a place that allows you to have fun in the outdoors throughout the year. That won’t be too difficult if you stop by Windham Mountain Adventure Park when you have the chance. You and your friends can fully enjoy Windham mountain activities by your mountain bikes for a ride through the woods, enjoy the scenery on skyrides, or hit some balls at some golf courses.

In case you plan on stopping by during the winter, the park provides hills for skiing and snowboarding. Dining and spas are also available to end the day on a relaxing note, and you have the option of using this spot to host a wedding or other special event.

Windham Mountain Adventure Park

Address: P.O Box 459, 19 Resort Drive, Windham, NY 12496

Website: Windham Mountain Adventure Park

6. European Craft Store

Editor's Note: Photo taken from the establishment's official social account

One of the most popular things for tourists to do is to take some kind of gift home for remembering their trip out of town. In that case, visitors to Windham should see what the European Craft Store has to offer. Antiques range from those perfect for decorating your living room to those that you can get for that special someone.

Among the more popular items at this store are jewelry boxes, carvings, shadow boxes and amber jewelry, and an emphasis is put on hand-made products. The store is also right next to Mountain Ski resort for those planning on going there sometime soon.

European Craft Store

Address: 6 Mill St, Windham, NY 12496

Website: European Craft Store

7. The Windham Path

Editor's Note: Photo taken from the establishment's official social account

For those who have a short weekend ahead of them or need some time to avoid anything too straining, a walk through the woods is one of the Windham activities you should try. If that’s what you see ahead of you, take a walk along the Windham Path the next time you’re in town, especially if you’re in the mood for some pleasant scenery.

You can take pictures of hills and stream while you walk along the path, and there’s always the option of taking a bike in case you want to bring your kids along and they want to get a little more active.

The Windham Path

Address: 4982 NY-23, Windham, NY 12496

Website: The Windham Path

8. Windham Vineyard & Winery

Editor's Note: Photo taken from the establishment's official social account

Pijou enjoying the sunshine.

Posted by Windham Vineyards and Winery on Thursday, July 16, 2015

Anyone who enjoys trying out new wine should give Windham Vineyard & Winery a shot the next time they feel like stopping by. This is one of the top Windham, NY, attractions as it comes with a selection of wine from other parts of the United States, as well as other countries like Portugal, Spain, France, Italy and South Africa, ensuring variety for visitors.

This spot is perfect for anyone coming off of Windham’s skiing hills or looking for somewhere to go when it’s a rainy day. Among the praises that visitors have given this place is the hospitality and helpfulness of the employees in selecting the right wine.

Windham Vineyard & Winery

Address: 11 Mt View Estates Rd, Windham, NY 12496

Facebook: Windham Vineyard & Winery

9. Windham Country Club

Editor's Note: Photo taken from the establishment's official social account

Posted by Windham Country Club on Monday, June 29, 2020

One of the best ways to take advantage of a sunny day is to hit some golf balls on your local course. If you see a weekend with great weather ahead of you, see what Windham Country Club can do for you. The course has often received praise for presenting a challenge to those who are new to the game and veterans looking for a challenge.

If your friends are dragging you along for a game, you can always just enjoy the scenery of the mountains and animals along the way. The bar and restaurant also offer a chance to drink and relax after a long game.

Windham Country Club

Address: 1 Country Club Rd, Windham, NH 03087

Website: Windham Country Club

10. Five State Lookout

Editor's Note: There's no photo available at the time of writing

For those looking for a spot that offers plenty of Windham mountain summer activities for friends and family out in the sun and the woods, Five State Lookout will have you covered pretty well. In addition to going on hikes that provide amazing views of the mountains below, this spot has lakes for those looking for a place to take their kayaks out, as well as camping grounds for those looking to stay the night.

Other activities that guests can take part in including mountain biking, fishing, golfing, hunting and horseback riding. Restaurants are available for those looking for a nice meal afterwards, as are art and culture centers for those who want to learn something new, as well.

Five State Lookout

Address: 7604 NY-23, Acra, NY 12405

Website: Five State Lookout

11. Windham Fine Arts

Editor's Note: Photo taken from the establishment's official social account

Going hiking or kayaking can get a little tiring after a while, and sometimes it’s best just to find a spot where you can just look at something unique. In that case, you should make visiting Windham Fine Arts a priority the next time you’re in town, especially if you want to check out some paintings that may inspire your own creativity.

Visitors will be able to learn about different artists and what inspired the creators of these pieces of art and how they developed their skills over time. Exhibitions also help visitors learn about different forms of art they may have never heard of before.

Windham Fine Arts

Address: 5380 NY-23, Windham, NY 12496

Website: Windham Fine Arts

12. Catskill Mountain Country Store & Restaurant

Editor's Note: Photo taken from the establishment's official social account

Knowing a spot in town that offers a variety of meals after a long day of adventure is important if you’re visiting a new town over the weekend. For those who don’t, they should consider what Catskill Mountain Country Store & Restaurant has for a nice breakfast, lunch or dinner.

Visitors will be happy to know that the breakfast menu is open all day, coming with pancakes, eggs, French toast, waffles and other options. Wraps, burgers and salads are available for lunch, and the gift shop next door has plenty of items for you to take home for remembering the trip.

Catskill Mountain Country Store & Restaurant

Address: 5510 NY-23, Windham, NY 12496

Website: Catskill Mountain Country Store & Restaurant

Visit over the weekend!

Windham, New York
Source: Photo by user Doug Kerr used under CC BY-SA 2.0

It’s important to find a town that offers both relaxing and active options for fun when you’re looking for a new place to visit over the weekend, especially if you’re into spending the day outside. Windham has you covered in that regard, providing parks for biking, hiking, fishing, kayaking and golfing for adrenaline seekers, as well as walking paths and art houses for those who don’t want to strain themselves too hard. This spot comes with restaurants and gift shops that will help end the day on a relaxing note as well. For those looking for an outdoor-centered weekend, make visiting Windham a priority.

Frequently asked questions about the best things to do in Windham, New York

1. What are the best attractions to visit in Windham?

Often referred to as “The Gem of Catskills”, Windham, NY, is definitely blessed with so many tourist attractions including Windham Mountain Adventure Park, Windham Country Club, and Windham Vineyard & Winery among many others.

2. What are the best activities in Windham?

Windham, NY, is a mountaintop town so you can definitely expect a wide array of outdoor activities that you can enjoy including hiking, golfing, mountain biking, sightseeing, birdwatching, and more.

Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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John Nassivera is a freelance writer and former news editor who's interests include traveling, science, fitness and lifestyle. He has visited several countries in Europe and traveled across the...Read more

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