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The Catskills have long been a popular vacation retreat for both NYC residents and non-city dwellers alike—with an abundance of spectacular mountain scenery; epic outdoor recreation; luxe lodgings; and a farm-to-table cuisine scene that’s a foodie’s dream come true, this New York State spot is the perfect place to get away from it all.

And while there are a number of amazing towns, villages, and hamlets to choose from, there’s just something extra special about the historic town of Windham—especially when the calendar pages make their inevitable turn into the cooler autumn months. Though the scenic mountain town is a four-season paradise that welcomes visitors all year round, fall is undoubtedly one of the best times to visit. Think dramatic Northern Catskills views bedecked in the brightest autumn colors; warm days and cooler, slightly chill nights; and outdoor activities and recreation that’s only made that much more beautiful after being touched by the cool, autumn air—all of this and more can be found in beautiful Windham.

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Outdoor Adventures In Windham

A year-round destination packed with recreational activities for the entire family, there’s always something in season in Windham. However, fall is an especially lovely time to explore this Hudson Valley haven and its outdoor activities, as the foliage is often spectacular, and the weather is breathtaking—full of crisp breezes and fresh mountain air; comfortable days when layers are a must; and starry nights with a slight chill in the air that hints of the winter ahead. Below are some of the best late summer/autumn outdoor activities to explore in Windham.

  • Outdoor enthusiasts will love Elm Ridge Forest and its miles of looped trails that are perfect for both mountain bikers and hikers of all skill levels. Parking area located on NYS Route 23 near Windham
  • The Windham Path offers some of the absolute best views in picturesque Windham—meadows, and woodlands to Great Northern Catskills views and access to the Batavia Kill Stream. 4982 NY-23, Windham
  • Fall hiking at its finest can be found on the Windham High Peak via the Elm Ridge Trail—undoubtedly one of the area’s most popular autumn treks. Moderately challenging, 5.9-mile out-and-back trail.
  • Explore Windham Mountain: home to scenic lift rides, a mountain bike park, golfing, dining, lodging, and more, this eponymous spot is a one-stop shop for the best of Windham outdoor activities. 19 Resort Drive
  • Fall for some of the best views in the Catskills—located less than 20 minutes from Windham, the two-tiered, over 250-foot tall Kaaterskill Falls is one of the most scenic spots in the area. The hike to the falls is approximately 1.4-miles roundtrip.

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Windham Town Travels

Though positively brimming with Catskill's charm and beauty, Windham is so much more than simply a scenic mountain town. A delightful Main Street bustling with locally-owned shops, restaurants, and quaint, small-town vibes, the historic hamlet has plenty of things to see and do in between treks into the great outdoors.

  • Situated on a sprawling four-acre property that overlooks nearby Windham Mountain, The Vineyard at Windham’s relaxed setting and superior sippers are the perfect way to soak up those lovely Catskills afternoon vibes. 11 Mount View Estates Road
  • Get those local feels at the Windham Farmer’s Market, where the region's best is on display—from fresh farm produce to artisanal products/crafts; there’s something for everyone at this eclectic marketplace. Turning Leaf Drive (just off Route 302). Farmer’s Market is Saturday 8:30 AM-12:30 PM through October 1, 2022
  • A refurbished 19th-century building hosts Windham Fine Arts—a cornerstone for contemporary local art (and sometimes music!) in the historic downtown area. 5380 Main St. Open Friday and Saturday 12 PM-5:30 PM; Sunday and Monday 12 PM-4 PM
  • Max and relax at The Windham Spa after a morning of downtown strolling. 16 Mitchell Hollow Road
  • Attend the 27th annual Windham Autumn Affair: one of the best ways to welcome fall with foliage, festivities, fun, and over 50 craft and food vendors lining Main Street. 5410 Route 23, Windham, October 9-10, 2022, 10 AM-5 PM
  • Browse downtown shops like Briars & Brambles Books and the Catskill Mountain Country Store

Where To Stay In Windham

There are a number of top-notch lodgings in Windham that make it easy for visitors to soak up the scenery and get rustic—all without sacrificing comfort, charm, and hospitality. From cozy B&Bs to boutique beauties, resort-style accommodations to historic houses, the area’s hotels are waiting to welcome guests with signature Catskills style.

  • Wylder Windham may be one of the town’s newest offerings, but it has already established itself as the place to be for year-round fun, adventure, relaxation—and, of course, those signature North Catskill views. Rates start at $225 and up/night.
  • With a cottage situated snugly on Windham’s Main Street and an inn just outside of town, the lovely Albergo Allegria Bed and Breakfast has plenty of options for those that want a more customizable stay. Elegantly rustic rooms and a world-class restaurant are just a few of the cool perks vacationers will enjoy in this classic lodging. Rooms start at $139 and up/night.
  • A beautiful boutique hotel and restaurant awaits guests of the posh Union + Post, a mountain oasis that’s conveniently located near many of Windham’s most popular attractions. Rates start at $220 and up/night.

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Where To Eat & Drink In Windham

Windham’s cuisine scene is all elevated, with contemporary Catskills flair and farm-to-table charm. And with plenty of distinctive offerings to choose from, guests will have their pick of top dining and drinking spots that are guaranteed to please any palate.

  • The Windham Local is fresh, delish, and oh-so Windham. 5410 Main St. $$-$$$
  • Catskill Mountain Country Store serves up all-day breakfast(!) and house-made faves—and is a great place to grab a picnic lunch, too. 5510 Route 23 $$
  • Bistro Brie and Bordeaux is an authentic French bistro that’s big on country charm. 5386 Route 23 $$-$$$
  • Crossroads Brewing Company is a chill hangout spot and brewpub with industrial charm and big Catskills vibes—and while there is no onsite kitchen, there are always food trucks outside to go with a pint (or two) 201 Water Street, Catskill, NY $
  • Deer Mountain Inn offers rustically upscale dining and lodging options just 20 minutes from Windham, complete with a mountain patio and cozy fireplaces; visitors will feel right at home. 790 County Road 25, Tannersville $$$+
  • A cozy four-season Scandinavian-inspired outdoor lounge welcomes visitors to Ze Windham Wine Bar—perfect for sipping, socializing, and noshing on small plates, Charcuterie, and snacks. 5369 Main Street $$-$$$

Often referred to as the “Gem of the Catskills,” the historic mountain town of Windham is the perfect four-season retreat for both lovers of relaxation and recreation. However, the stunning area really shines in the fall when the balmy temps give way to crisp fall days and cool, chill nights. An idyllic place to get outdoors or simply escape from the hustle and bustle of everyday life, wonderful Windham is the perfect autumn Catskills getaway.