Meandering In: Windham, New York

Windham, NY
Credit: Adobe

Known as the “Gem of the Catskills,” Windham is known for its ski resort and incredible mountain scenery. If you are looking for an escape into the wilderness, drive through the Catskill mountains and visit this idyllic town. 

Best Time to Visit

Each season is beautiful in its own way, and the temperatures only get quite warm in July/August

Places to Go and See

Windham Mountain Club

Meandering In: Windham, New York
Overlooking the valley with skiers going downhill, Windham, New York, USA

Satisfy your skiing or snowboarding craving at Windham Mountain. Rent equipment right at the mountain or bring your own to ride down more than 10 different trails spread across the mountain. When you get too cold, head into the lodge for a warm cup of hot chocolate and get ready for the next ride down.

  • Hours: Winter lifts are open M-F 9-4, Sat-Sun 8-4; summer months times may vary to hike the mountain
  • Best Time: November-April, when all the snow is on the mountain and lifts are open
  • Price: varies based on day reserved and type of ticket

Christman’s Windham House

A combination of hotel and golf course, Christman’s will keep you entertained in the summer or the winter. Reserve a cozy room just one mile away from Windham mountain and head over to ski, or just stop by during the summer and try out their 18 hole mountain course or their 18 hole valley course.

  • Hours: Mon-Sun 7-10
  • Best Time: During the summer to take advantage of their well-groomed course
  • Price: Ranging from $30-$85 depending on number of holes and which course you choose to play on

The Windham Path

Meandering In: Windham, New York
Credit: Markus Spiske

Take a walk on this 1.5 mile loop right off of Route 23 and see sights such as the Batavia Kill stream and the Northern Catskills looming high above you. You can bring your dog with you, just make sure they are on a leash.

  • Hours: 24 Hrs
  • Best Time: Warmer dry weather, or during the Fall to see the changing colors
  • Price: Free

Five State Lookout

Credit: Clay Banks

Right off of Route 23, take a moment to stop at the Five State Lookout, where on a clear day you can see the mountain ranges of five states. You’ll be able to see the White Mountains of New Hampshire, the Green Mountains of Vermont, the Berkshire Mountains of Massachusetts, the Helderberg Mountains of New York and the Connecticut Valley.

  • Hours: 24 Hrs 
  • Best Time: Sunny clear day
  • Price: Free

The Windham Spa

Founded by Antonia in 2006, the Windham Spa aims to use the best organic products and the latest technology to keep you refreshed and relaxed. Whether you need a deep massage or a cleansing facial, they will provide you with unpretentious service to make your stay amazing.

  • Hours: Summer Hours – Wed 3-6, Thurs & Fri 10-6, Sat 10-5
  • Best Time: Anytime as it is all indoors
  • Price: Ranges from ~$120-385, depending on the service selected

Windham Vineyard & Winery

Sitting on 4 acres of land, the Windham Vineyard is the place to go to try not only their delicious wines, but selections from across New York State. Take a trip by yourself or invite friends to join you and dive into the tasting room, where you can have great wine and even better conversations.

  • Hours: Tasting Room Fri-Sun 12-7
  • Best Time: Anytime as the tasting room is indoors
  • Price: $35-45 for tastings, other options vary

Hidden Gems

Windham Theatre

Meandering In: Windham, New York
Credit: Meg Boulden

Take a trip over to the local Windham Theatre and see some of the newest movies on the big screen. For seating, choose either the standard movie theater seats or sit down at a table and chairs and enjoy your snacks while the movie plays.

  • Hours: Mon-Fri 4:30/7:30, Sat-Sun 1:30/4:30/7:30
  • Best Time: Anytime, indoors
  • Price: $11

Windham Fine Arts

Displayed in an 1855 building that was restored and opened in 2003, the Windham Fine Arts gallery presents both locally and internationally acclaimed artists across 3,000 square feet. Visit and view the permanent collection, or enjoy the varying exhibitions throughout the year.

  • Hours: Fri 12-5, Sat 12-5:30, Sun 12-4
  • Best Time: Anytime, indoors
  • Price: Free

European Craft Store

Specializing in homemade wooden crafts, you can find a unique gift for your loved one at the European Craft store. They also have amber jewelry, nesting dolls, Polish pottery, and sheepskin baby booties, and many other items in their quaint shop.

  • Hours: Sat 10-5, and by appointment
  • Best Time: Anytime as it is indoors
  • Price: Varies based on what you buy

Briars and Brambles Books

Coined as the “go-to Indie bookstore in the heart of the Catskill Mountains,” Briars and Brambles has a large selection of tangible and audiobooks to choose from. Check in periodically for special events, and see what the staff are reading, and maybe you’ll find the book for you.

  • Hours: Sun-Wed 9-5, Thurs-Sat 9-6
  • Best Time: Anytime
  • Price: Varies based on how many books you walk out with

Elm Ridge Wild Forest

Located in the northeast corner of the Catskill Forest Preserve, the 1,355 acre forest contains a 1.5 mile portion of the Escarpment Trail, the 1.1 mile Elm Ridge Trail, and others adding up to more than 25 miles in trails.

  • Hours: Year-round
  • Best Time: Warm sunny day
  • Price: Free

Windham Country Club

Windham Country Club
Windham Country Club

Owned by Windham Mountain, this newly renovated country club is open to the public but provides a private club atmosphere amongst the Catskill mountains. Play 18 holes on the scenic course, and once you’re done head over to Mulligan’s Pub and have a much-deserved meal.

  • Hours: Mon-Thurs 8-6, Fri-Sun 7-6
  • Best Time: During the summer
  • Price: Ranging from $45-95 depending on tee-off times and days of the week

Top Restaurants

Chicken Run

The Chicken Run
Windham Chicken Run

Situated right at the bottom of Windham Mountain, the Chicken Run is a sprawling rustic restaurant that aims to serve comfort food that’ll keep you satiated. Combined with attentive service and quick turnaround, check out the four different rooms to sit in, the large u-shaped bar, or head outside to listen to live music and sit by the fire pit.

  • Hours: Tues & Wed 4-8:30, Thurs 12-8:30, Fri & Sat 12-9, Sun 12-8
  • Featured Food: The Chicken Run Combo / Famous Grilled Sausage
  • Featured Drink: Ginger Lemonade / Blueberry Lemonade

Tap House Grille

Presenting a selection of local and international beer, wine, and spirits, the Tap House Grille is the perfect place to watch a sports game, or just hang out with friends. Along with well-crafted food dishes, you will not leave hungry from this establishment. 

  • Hours: Mon-Sun 12-12
  • Featured Food: Premium Taphouse Burger / Taphouse Baby Back Ribs
  • Featured Drink: Grandma’s Peach Tea / Taphouse Rose Peach Sangria

Lilly’s Steaks and Cocktails

Bringing a little bit of Ireland to the Catskills, Lilly’s Steaks and Cocktails is a sophisticated yet comfortable establishment that offers great cuts of meat and handmade cocktails. Enjoy a meal on a weekday, or drop in on Football Sunday and watch your favorite team play.

  • Hours: Closed Wed, Sun-Tues 4-11, Thurs & Fri 4-11, Sat Brunch 11-3, Dinner 4-11
  • Featured Food: Cowboy Delmonico / Lilly’s Pork Chops
  • Featured Drink: Lilly’s Dirty / Windham Kiss


Meandering In: Windham, New York
Credit: Kelsey Knight

Opened 36 years ago, Brandywine has been serving classic flavors to Italian food lovers for over three decades. Take a seat at the bar or sit at one of their many tables and enjoy a glass of wine that perfectly complements your meal.

  • Hours: Closed Mon, Tues-Thurs 4-9, Fri 4-9:30, Sat 1-9:30, Sun 1-9
  • Featured Food: Seafood Fra Diavolo / Chicken Francese
  • Featured Drink: Large selection of white and red wines

Millrock Restaurant

Opening its doors in the fall of 1996, the Millrock has been an italian staple ever since, located right on main street in Windham. Showcasing local ingredients in their fresh seafood, thin-crust pizza, and savory meats, you will have no problem finding a delicious entree to enjoy.

Top Hotels

Winwood Inn

  • ~$100/night
  • Featured Amenities: Free WiFi, Outdoor Pool, Golf, Tennis, Horseback Riding, Game Room
  • Hotel Information: Check in 3pm, Check out 10am, Free Parking

Take a trip into the mountains and visit Windham, New York. Whether you decide to come during the peak of ski season, or wait until warmer weather so you can golf, there is something to do all year long in this quaint town nestled in the Catskills.

The Haus Windham

  • ~$150/night
  • Featured Amenities: Free WiFi, Air Conditioning, Coffee Maker, Kitchen in some rooms, Extra-charge Pet Friendly, Private Bathroom
  • Hotel Information: Check in 2pm, Check out 11am, Free Parking

Hotel Vienna

  • ~$200/night
  • Featured Amenities: Free WiFi, Free Breakfast, Golf, Horseback riding, Indoor Pool, Hot Tub
  • Hotel Information: Check in 2pm, Check out 11am, Free Parking

Eastwind Hotel Windham

  • ~$300/night
  • Featured Amenities: Free WiFi, Free Breakfast, Air Conditioning, Pet Friendly, Kid Friendly, Smoke Free Property 
  • Hotel Information: Check in 3pm, Check out 10am, Free Parking

Wylder Hotel Windham

  • ~$400/night
  • Featured Amenities: Free WiFi, In-house Restaurant, Golf, Game Room, Outdoor Pool, Sauna
  • Hotel Information: Check in 3pm, Check out 11am, Free Parking

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Alexandria is a News Editor, writer, and reader of all things literature. She graduated from the State University of... More about Alexandria Wyckoff

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