The only thing better than sweater weather in the Northeast is enjoying it in New York’s Sullivan Catskills. Plan now to embark on an adventure to this renowned vacationland, just 90 miles from Manhattan for a haven full of vibrant small-town charm. 

The countryside becomes a stunning kaleidoscope of color during fall foliage season. Amplifying these red, gold, and orange hues is the colorful Sullivan Catskills Dove Trail. It’s a collection of 70+ hand-painted Dove sculptures— in tribute to the Woodstock Music and Arts Festival held here in 1969. To help guide you to each dove location, you can download the trail map at SullivanCatskills.com or find each dove’s location on the free Sullivan Catskills Go app. The very first dove is at Bethel Woods Center for Arts, the site of the Woodstock festival, where you can plan your visit around Harvest Festival, every Sunday through October 6. It’s a farmers’ and artists’ market featuring the bounty, talent, and beauty of the region. 

Outdoor enthusiasts, immerse yourself in water and land adventures. In the western part of the Sullivan Catskills, go rafting, canoeing, or kayaking down the Delaware River or fish in the rivers and streams (Delaware, Willowemoc, Neversink) where American dry fly fishing was born. The boating liveries typically close by mid-late October, so plan accordingly. By car, you can enjoy the foliage along the Upper Delaware Scenic Byway. Stretch your legs with a hike on the Tusten Mountain Trail or one of the numerous other trails featured on Trailkeeper.org to guide your on-foot journey. Further to the east, The Neversink Reservoir is another gorgeous place to boat in autumn. Before or after, grab a to-go lunch or dinner from the Neversink General Store. Got pedal power? You can ride a bike on the O&W Rail Trail, with rentals available at Fortress Bikes in Hurleyville or Cinder Tracks in Mountaindale. Then, enjoy a meal, cocktail, or nosh at The Tango Café, Forage and Gather or La Salumina in Hurleyville. Or check out The Dale in Mountaindale, where the pizza is absolutely to die for.

Then, it’s time to renew your body and soul. Try Hemlock Neversink, Crystal Life Spa at Resorts World Catskills, Yo1 Health Resort, or Hemlock Spa at Kenoza Hall. As a bonus, each of these locations also offers dining and full-service accommodations set in lovely rural surroundings. 

Hungry? Early Fall provides the perfect backdrop for outdoor dining, beer, wine, and cocktails. Check out Smoke Joint Catskills in Livingston Manor, Big Kev’s in White Lake and Chick E Ribs in Liberty for BBQ. While you’re there, visit Sunshine Colony Wine Bar, Catskill Brewery, brick oven pizza at the Kaatskeller, or Upward Brewery. There are so many inventive chefs here, and Restaurant Week, taking place October 28 through November 10, provides the opportunity to check out their culinary skills. Some noteworthy restaurants to consider include Pasta D’Oro in Wurtsboro; Cellaio Steakhouse at Resorts World Catskills; Tavern on Main in Jeffersonville; Conover Club in Callicoon Center; The Junction, The Yarra and Northern Farmhouse Pasta in Roscoe; The Debruce in Livingston Manor; The Heron, The Laundrette, and Tusten Cup in Narrowsburg; Cochecton Fire Station and The Pump House in Cochecton; The Corner Piazza and The Old Homestead in Eldred; The Tavern at Forestburgh Playhouse in Forestburgh; Creek House Grill and the Western Supper Club in Callicoon, and Solaia in Monticello. 

The Good Taste Beverage Trail is a favorite for craft beer, wine, cider, and spirits lovers. Sample the award-winning flavors while you chat with the proprietors and learn their stories. There’s a former armed services vet, a husband-and-wife brew team hailing from Ukraine, a publisher turned distiller, and a vintner who quit his day job to craft wine. Want to learn more about how to taste and evaluate wine, as well as its characteristics, terminology, and history? Check out the wine classes at Terra Space in Jeffersonville, led by A.J. Ojeda-Pons, a WSET (Wine Spirt and Education Trust) certified Sommelier. 

As the trees settle into dormancy and the weather turns colder, Halloween and the holiday season come to life in the Sullivan Catskills. A must-see at Forestburgh Playhouse is the annual stage performance of Rocky Horror Live on Fridays in October.  At Bethel Woods Center for the Arts Peace, Love & Pumpkins, an enchanting walk-through Halloween experience and marketplace runs from October 11-27. Then, beginning November 29 and running through December 29, it’s the Peace, Love & Lights drive-through holiday light show (with walk-only Mondays).

There is so much more to explore and experience— artisanal shopping, farmers’ markets, restaurants, art galleries, and fall festivals— throughout the charming small towns of Wurtsboro, Mountaindale, Liberty, Bethel, Jeffersonville, Livingston Manor, Roscoe, and others. With all there is to do here, you’ll surely be looking for a place to stay in the area.

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The full-service resorts—Resorts World Catskills, Yo1 Wellness Center, and Villa Roma—cater to your every need. Vacation rentals are plentiful, and there are charming boutique inns, including Kenoza Hall, Callicoon Hills, The Bradstan at The Eldred Preserve; Chatwal Lodge at the Chapin Estate; cabins at Antrim Streamside, glamping and vintage RVs at The Domes at Catskills, Boheme Retreats and over a dozen more. To book an autumn visit and plan your itinerary, visit SullivanCatskills.com.