Photo: Michael Carnevale/Wylder Windham

How to Make the Most of a Trip to the 'Gem of the Catskills'

New York Travel Outdoor Epic Stays
by Nickolaus Hines Jun 20, 2022

The Catskills have long been an escape for New Yorkers. Abundant hiking, winter sports, and small towns are the perfect antidote for anyone looking to step away from city life for a bit. Windham, established in 1798 and one of the oldest small towns, is one of the stand-out Catskill destinations — so much so that it’s known as the “Gem of the Catskills.”

Golf and nearby mountain bike trails can fill summer days, while 1,600 vertical feet of skiing occupies the outdoorsy set in the winter. Art, boutique shops, restaurants, and The Vineyard at Windham make the town just as much a spot for relaxation as adventure. All that’s on offer made Windham the perfect place for Wylder Windham, a resort that will debut in August 2022 on 20 acres near the Batavia Kill. The third all-season resort from Wylder Hotels will have 110 rooms spread across seven restored historic lodges, inns, manors, and cottages that were once the historic Thompson House.

The opening comes at one of the best times for a trip to this part of the Catskills.

“Windham is a mountain town, so we’re surrounded by beautiful scenery, hiking trails, kayaking, skiing, and so much more,” says John Flannigan, the owner and founder of Wylder Hotels. “The town has recently announced a comprehensive plan, which includes improving access to outdoor activities like hiking trails, swimming areas, and boating facilities, and will continue to honor its promise in preserving local history and the town’s character.”

From Wylder’s on-site activities like pickleball, fire pits, a pool, and tubing, to the surrounding natural environment and small towns, Flannigan shares how to make the most of the Gem of the Catskills.

Photo: Michael Carnevale/Wylder Windham

This interview has been edited for length and clarity.

Matador Network: What biking trails do you especially recommend to see the best of the region?

John Flannigan: Windham Mountain Bike Park has bike trails for all levels — beginner, intermediate, and expert — with outstanding views. It offers a truly unique downhill riding experience, and the longest jump trail on the East Coast. Outstanding natural Catskill Mountain terrain has been expertly developed by world renowned trail designers Gravity Logic. Miles of trails are serviced by the brand new Westside Six, a high speed six passenger lift, so you’ll never need to pedal uphill.

What’s your Windham favorite activity to do in each season?

Winter: Snow Shoeing is a really fun way to hike and see nature. It can be a gentle walk or a tough workout. It is also a great way to see the trails from a new angle. To snowshoe at Windham Mountain, a $5 ticket can be purchased at the base lodge, and they also have snowshoes available for student lessons.

Spring: Golfing at the Windham Country Club. It has an 18-hole public golf course with a private club atmosphere. This course has scenic and challenging fairways that follow the Batavia Kill and spectacular views of the Great Northern Catskills. Designed in 1928, the golf course has undergone complete renovation under the ownership of Windham Mountain Resort, returning the Club to its former glory while maintaining its longstanding tradition.

Summer: Wine tasting at The Vineyard at Windham. The vineyard overlooks Windham Mountain and its surrounding year-round beauty. They produce wine and source the best-rated wines that New York State has to offer from the Finger Lakes all the way down to the renowned North & South Forks of Long Island- all under one roof.

Fall: Hiking the Windham High Peak via Elm Ridge Trail. This 5.9-mile out-and-back trail near Windham is the most popular trail in the area. This trail is generally considered a moderately challenging route that takes an average of 3 hours and 15 minutes to complete.

What are your favorite Catskill waterfalls to hike to?

Kaaterskill falls waterfall in the New York Catskill mountains

Photo: James Parascandola/Shutterstock

I love hiking at Kaaterskill Falls, which is about 15 miles from Wylder Windham. It’s a relatively easy hike with some of the most beautiful views of the Catskills and a photo worthy waterfall that can’t be missed. In fact, Kaaterskill Falls has been inspiration for many artists, filmmakers, and photographers, including the famous Kaaterskills Falls painting by British-American painter Thomas Cole.

What are your favorite Windham hikes?

Windham Path has amazing views and open space, and it’s an easy yet inspiring hike. The Path is great and it’s all downtown and accessible. The first phase of the Windham Path is a 1.5-mile loop accessed by a parking area on Route 23, and the second phase is a half-mile section that connects the business area of South Street and Route 296 to the first phase loop. The Windham Path provides the only public access to the Batavia Kill stream in Windham and meanders through meadows and woodlands and across bridges providing fantastic views of the Great Northern Catskills. It’s also a great hike to take with your kids and pets that provides plenty of fresh air and nature galore.

What are your favorite restaurants in the area?

Babblers for obvious reasons! Situated next to the Batavia Kill River, Babblers captures the energy of Windham. Laidback in nature and welcoming in spirit, it’s a place that locals post up year-round and rub shoulders with visitors. The vibe is spirited and familiar, the food and libations are strong.

Deer Mountain Inn is also fantastic. Whether it’s for a small plate and drink on the mountain-view patio, a leisurely three-course meal near the cozy fireplace, or dessert and a digestif at the full-service bar, which offers classic spirits, hand-crafted cocktails, a smart wine list, and local brews.

What about the best places to grab a drink?

Drinks on The Manor Inn Porch on property is a majestic experience. Union + Post nearby are our friends and do a great job. They are a boutique hotel and restaurant that also offer four-season experience with natural surroundings.

Photo: Michael Carnevale/Wylder Windham

Wylder Windham is pet friendly. What are your favorite things to do in the Catskills with a dog?

Besides all the hiking trails, I love visiting local breweries, many of which are dog friendly. Crossroads Brewing Company has a great selection of beers to enjoy and located right next to the Hudson River for awesome views.

What’s your favorite nearby Catskills small town to visit?

Phoenicia is a lovely chill spot. There are a couple of big events in the summer worth checking out, the largest being The Festival of the Voice in August and the Shandaken Artist Studio Tour in June. There’s lots of outdoorsy stuff to do; many difficult hikes, easy strolls, and even tubing down the Esopus Creek. The main strip in town has several great restaurants, galleries, and a couple of shops.

What are your favorite shops for local Catskill goods?

Windham Farmers Market on weekends near Windham Local is great! The market includes vendors selling fresh fruits, vegetables, herbs, cheeses, honey, maple syrup, baked goods, meats, eggs, flowers, soaps and essential oils, crafts, and more.

There’s also Windham Fine Arts. This contemporary art gallery features a wide array of artists and craftspeople with an ever-changing collection that includes abstract art, traditional landscapes, sculpture, prints, photography and everything in between.

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