Blake Walsh

20 Best Things to Do in Windham, NY

  • Published 2023/01/06

When planning a weekend getaway, those who love being active and want to relax should look for destinations that provide both.

Windham, New York, is a must-see destination for you and your buddies if you fall into this category.

Windham provides everything you need for the ideal small-town getaway all year round.

People call this town the “Gem of the Catskills” for its natural charm and cultural offerings.

As of the 2010 census, it is home to 1,703 people.

Many of the town’s first residents were from Connecticut and other regions of New England.

Therefore it is likely that the town took its name from Windham County.

People also call it the “Land in the Sky.”

The three hamlets Hensonville, Maplecrest, and Windham, make up the current town of Windham.

Popular with couples and families alike, it has an abundance of entertainment options for all types of people.

Read on to find out all sorts of activities you can do in Windham, New York.

Try Different Outdoor Adventures at Windham Mountain

Fall scene at Windham Mountain

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A spot where you may enjoy the great outdoors all year round is hard to come by.

If you get an opportunity to visit Windham Mountain Adventure Park, you won’t have a problem accomplishing this goal.

Windham Mountain is a place to be lost and found again, to discover spectacular adventure, and to experience how amazing it is to spend time with your loved ones in the great outdoors.

Covered bridge at Windham Mountain

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Ride your bike through the woods, take a Skyride, or play a round of golf.

It is possible to go skiing and snowboarding at the park if you visit during the winter months.

In addition to dining establishments and spas, this location also caters to weddings or other special events.

The waters of Windham Mountain

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Hike Along The Windham Path

A stroll in the woods is an excellent alternative if you have a brief weekend or need to dodge anything too taxing.

Assuming you feel the itch to see some lovely scenery, take a stroll on the Windham Path when you’re in town.

Its first phase consists of 1.5 miles that can be reached from a parking lot at Route 23, while the second phase is a 12-mile segment that links the South Street and Route 296 commercial districts with the first phase loop.

As Batavia Kill stream’s only public entry point, the Windham Path is a fantastic way to explore the area while taking in the stunning vistas of the Catskill Mountains in the background.

Take photographs of hills and streams while you walk, or bring a bike if you want to be a bit more active while here.

Go Horseriding at Mountain Brook Farm

This farm has been in the same family for more than 150 years, making it one-of-a-kind!

The barn you see standing today, completed in 1918, was a pioneering project with a workforce of double that of its competitors in the area.

The last generation agreed to cease the dairy farm in January 1998, Nancy and Edsall Partridge.

In 2003, they transformed the barn and surrounding field into an equestrian facility.

Nancy designed the tack rooms and stables that you see now within the barn after it received a complete repair.

The property lies on Northern Catskills, about seven miles outside Windham.

Two extensive state forests—Ashland Pinnacle and Huntersfield—surround the area.

This scene provides meadows on hilly canvas, with daisies and dandelions strewn about the sound of rushing water around every corner and the rich fragrances.

In the end, you’ll have a lasting impression that’s unlike anything else you’ve experienced.

Join the Annual Tour of the Catskills Pro-Am Bicycle Road Race

More than 250 cyclists from all around the globe compete in this Pro-Am cycling road event.

Catskill Mountains hamlet Windham is home to America’s most prestigious cycling competition, the Tour of Catskills (TCC).

These mountains, people, and landscapes come to life via this festival.

One of America’s most challenging cycling races was introduced in 2012 when the ‘Devil’s Kitchen Climb’ was added as an option for amateurs and pros alike.

Tee Off at Windham Country Club

There are several ways you can make use of the warm weather in Windham, including golfing at the course nearest you.

Windham Country Club can help you get the most out of a sunny weekend.

The course has garnered many accolades for being challenging for both newcomers and veterans who are seeking a challenge.

If you wish to play a game with your companions, take in the environment and wildlife as you go.

After a long game, its bar and restaurant provide a place to unwind.

Sip Wine at The Vineyard at Windham

This winery in Windham, New York, is worth visiting for anybody who likes to experiment with their palates.

This is a great place to go after a day of skiing in Windham or on a wet day when you don’t want to be stuck indoors.

Employees at this establishment have received several compliments for their warmth and assistance in helping customers choose a bottle of wine.

Check Out the Contemporary Exhibits in Windham Fine Arts

Sometimes it’s better to sit back and enjoy the scenery rather than go trekking or kayaking, which may be exhausting after a while.

There are a lot of paintings at Windham Fine Arts that might inspire you, so if you’re ever in the area, make a point of stopping in.

Windham Fine Arts is a modern art gallery in Windham, New York.

After a three-year renovation of its original 1855 structure, it finally opened its doors to the public in 2001.

It stands on a 3,000 square-foot space meticulously designed, with a local charm.

Art exhibitions and cultural activities occur throughout the year at the gallery, which features both local and foreign artists and exhibits both solo and group work.

You may learn about various artists and what motivated the makers of these works of art, and how they improved their abilities through time.

Additionally, exhibitions allow people to learn about new types of art that they may not have previously encountered.

Grab Some Fresh Produce From Catskill Mountain Country Store – Windham

A bakery, a gift store, a full-service restaurant, a playground, and quiet places for residents and visitors are all part of this unique rural market.

Pop Pop Siegfried (Natasha’s Great Grandpop) founded a modest business in Windham, New York, offering local crafts, fresh vegetables, gourmet meals, and baked goods prepared from Pop Pop Siegfried’s recipes.

To celebrate their 1995 acquisition of Windham Gardens, they built a garden center, zoo, and walking routes.

Then in 2000, they expanded their restaurant by establishing a new extension

It offers all-day breakfast, including eggs, pancakes, French toast, and waffles.

Meanwhile, lunch options include wraps, burgers, and salads, and the gift store next door provides a wide selection of souvenirs to remember your vacation.

See the Antique Car Collection of Christman’s Windham House

This historic building started as a farm in 1805 and later served as a Drovers Tavern along the Catskill Turnpike.

When the current owners purchased The Windham House from its previous occupants in 1952, the core components of the tavern were still intact.

There was a chicken coop, hog house, a horse barn with three stories, a sap house for making maple syrup, working horses, and equipment to harvest ice, as well as an ice pond on the 300-acre property.

Even the nets used to catch carrier pigeons are still in place.

Stoney Brook’s home, where the caretaker resided, and the big Inn, which could accommodate a maximum of 70 guests, completed the property’s lodging options.

Christman’s Windham House developed throughout the following 50 years.

It adapts to today’s tourists just as it did in the past.

Colonial tool displays and vintage automobiles are on display at this historic building.

Additionally, it serves as an inn and has a golf course and restaurant, all of which contribute to making your time in Windham enjoyable.

Explore Various Shops During Windham’s Annual Autumn Affair

Windham’s Annual Autumn Affair is an annual event that includes beer and wine tastings, a wellness tent, and over fifty exhibitors running both sides of Main Street with local goods and cuisine.

The event also includes DJs and live music to keep things going throughout.

Stop by the Art Show at Centre Church if you have time.

Pony rides, pumpkin decorating, face painting, magic acts, and much more will be available for free to children of all ages.

Check the event’s official website to get updated about the affair dates.

Witness the SkyGlow Laser Show

The SkyGlow Laser Display is a free laser light show on the snow.

This event, which began in 2020, takes place regularly at Windham Mountain.

Full-color laser projections paired with an incredible soundtrack of modern tunes are guaranteed to have you up and dancing.

Before the concert, there is a DJ who will get you in the mood.

Glow wristbands and 3D glasses are also available for purchase in the resort’s restaurant, along with a variety of food and drink deals.

Be Amazed at the Different Tricks at Magic on Main

Magic on Main – An Intimate Parlor Experience with Magician Sean Doolan takes place in a historic house on Main Street, where Sean’s private library transforms into an intimate setting for a magic presentation.

The mind-blowing magic acts feature Sean’s tale of transforming from a trial attorney to a magician.

With a sleight of hand and trial experience, Sean’s act showcases the human mind’s inability to overcome its constraints.

It’s no secret that guests like Sean since he’s so dedicated to his craft.

He also understands how to turn a magic trick into an entertaining show for his audience.

This man has an extraordinary capacity to wow and connects people with his unique perspective.

Bring Home a Good Read From Briars & Brambles Books

Located in the Catskill Mountains, Briars & Brambles Books is a small independent bookshop with an extensive inventory in various genres and sub-sub-categories.

Over 6,000 professionally-curated publications, local and regional authors, games, puzzles, stationery, and little tabletop things that make lovely presents are available.

There is a functioning fireplace in the center of the shop.

However, there is just a tiny space of sitting available.

It also offers a segment called “Let’s Read Together” for youngsters under six.

Gifts for every occasion are also available at the store to make your shopping experience even better.

Buy Exquisite Handmade Jewelry From European Craft Store

Travelers usually bring home a souvenir of their journey to a different city as a way to remember their experience.

In such a case, tourists to Windham should check out the European Craft Store, located in the town square.

Antiques might vary and are great for adorning your living room with those perfect for giving to that particular someone in your life.

Carvings, Jewelry boxes, shadow boxes, and amber jewelry are among the most popular goods available at this shop, which focuses on handmade items.

For those intending to visit Mountain Ski Resort soon, the shop is also conveniently located nearby.

Book a Pamper Day at Windham Spa

The Windham Spa, established in 2006 by Antonia, is a pioneer in natural, biodynamic, and non-invasive skincare products.

They provide a collection of only the best handcrafted, limited edition, and ecologically friendly items they like, test, and use daily.

Facials at Windham Spa include Eminence Organic Skincare products handcrafted in Hungary.

Eminence is a family-owned, vegan, and cruelty-free brand in organic skincare with a focus on sustainability.

Customers get unmatched results with their revolutionary face treatments and the most recent non-invasive skincare technologies.

Grab Supplies at Windham Mountain Outfitters

All the supplies and equipment you’ll need to delight yourself on the mountain adventure are available at Windham Mountain Outfitters.

They stock all the leading market brands in every size for a great fit, whether you’re seeking to buy or rent.

Top-tier front suspension mountain bikes, prototype bikes, apparel, and accessories are available in their wide range of summer biking equipment to get you ready to go.

Windham Mountain Outfitters provides summer mountain bikes for riders of all ability levels.

They’re delighted to assist you in selecting the model that best suits your needs and financial situation.

Additionally, a comprehensive selection of top-notch boards, skis, boots, bindings, clothes, and accessories are for purchase or rental, helping you get ready for the winter season.

Prepare for a Fun-Filled Day with the Family at Windham Mountain Tubing Park

With thrilling snow tubing, kid-sized snowmobiles, and a cozy lodge, the Windham Mountain Tubing Park provides daytime and evening family entertainment during the winter.

Before taking to the tubing lanes, stop by Drop Zone for a cup of hot chocolate, sandwiches, hot dogs, nutrition boxes, and other goodies for the entire family.

No prior knowledge is necessary to access family-friendly enjoyment.

Bring your children to experience the kids-only Arctic Cat snowmobiles available at the Tubing Park.

Hit the oval snowmaking track elevating the winter pleasure to a new level.

In addition to regular business hours on holidays, Windham Mountain Tubing Park is accessible on Saturdays from 11 am to 8 pm and Sundays from 11 am to 7 pm.

Spend Your Vacation at Hotel Vienna

Hotel Vienna is a haven for nature enthusiasts and those looking for a tranquil rural experience, set in the middle of the Windham Path.

On approximately nine acres of serene land in the Catskills, there is a 29-room hotel and a three-bedroom log cabin house.

Take your dog on a neighborhood hike, spend the day riding or strolling the Windham Path in their yard, or simply unwind by one of their fire pits beneath the stars.

The numerous mountain terraces and outdoor fire pits offer the ideal setting for a peaceful sunrise or a leisurely evening.

Hotel Vienna in Windham, New York, is the perfect retreat for couples and special events, whether you’re here for the mountains, trekking, or simply vacationing.

Watch a Movie or Play Golf at Windham Theatre

Come to the Windam Theatre Triplex for a movie, dinner, and a round of mini golf.

Discover the exquisite lodging options and make a reservation from their elegant four-bedroom, two-king bedroom apartment or historic, one-of-a-kind Caboose Rental.

Snack at Subway’s Subs and Wraps, which are great for lunch, birthdays, club events, business celebrations, picnics, and parties – wherever and whenever there is a cheerful, hungry group to feed.

Additionally, Carvel’s extensive selection of distinctive ice cream desserts provides a wonderful opportunity to surprise someone special.

Experience the most complex mini golf/putting layout in the Hudson Valley at the Windham Theatre Complex.

Other Things to Do Nearby

Hunt Some Wild Turkey at Catskill Forest Preserve

Wildlife abounds in Catskill Forest Preserve.

Deer, bear, and bobcat are all big cats, but Catskill Forest Preserve offers a variety of smaller animals, such as porcupine and fisher.

It is also home to various birds, many of which are abundant in the area.

The region is a famous hunting location for both small and large-sized wildlife.

Hunters of the upland game often target ruffed grouse, wild turkey, and woodcock as their primary prey.

Final Thoughts

Whether you’re looking for adventure, strolling routes, art galleries, or don’t want to exert yourself too much, Windham has your back!

Restaurants and gift stores abound here so that you can wind down at the end of the day in style.

Windham should be at the top of your list if you want to spend a relaxing weekend in the great outdoors.

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