Why the Catskills Remain the Perfect Fall Getaway From NYC

The England-born Cole began painting this part of upstate New York in the 1820s. A founding member of the Hudson River School of artists, he’s best known for his romantic renderings of the waterway. But he frequently painted the Catskill mountains, which he portrayed as lush, unpeopled, and suffused with an almost otherworldly light.

Cole worked in the region around the time that it started to attract tourists, many of whom were drawn to the newly opened Catskill Mountain House, which was situated in a pine grove high up in what is now the Kaaterskill Wild Forest. The grand hotel was only a short distance from the edge of a cliff, providing guests with not only sublime views of the Hudson River but also the thrill of being just steps away from plummeting to their deaths. In one of Cole’s paintings, a figure sits at the foot of the precipice, sketching the hotel’s white Federalist façade above.

Inside Cole’s house, which is now a museum, Caleb and I inspected his paint kit and portable folding chair, and then watched a video in which an actor read from the artist’s letters. Cole was troubled by the recent arrival of the railroad and the destruction of the Catskills’ forests by new industries, particularly tanning. “I cannot but express my sorrow that the beauty of such landscapes is quickly passing away,” he wrote.

It struck me that if Cole were alive today, he would have to concede that the Catskills have retained their beauty, thanks largely to protections instituted by New York State in the early 20th century. After visiting the painter’s home, Caleb and I ventured into Catskill Park, some 286,000 acres of high peaks and luxurious woodlands spread across four counties. A couple of days later, we hiked to the spot where the Catskill Mountain House once stood and saw the same view that dazzled guests until the hotel was shuttered during World War II. Caleb photographed graffiti that early visitors had carved at the cliff’s edge. We had the site to ourselves, and the scene felt primordial and peaceful.

Eastwind’s most beguiling element is hidden from view. Drive behind the renovated roadside motor inn that makes up the main building and you’ll find sleek wooden Scandinavian-style glamping structures in a field strung with fairy lights. Our oblong cabin was designed with the craftiness of a Rubik’s Cube: a living room opened onto an outdoor terrace; a utilitarian bathroom and study were tucked under a sleeping loft.

In the evenings, Caleb and I sat beside our private firepit and polished off the complimentary s’mores kit, while the starry sky and the distant sound of coyotes created the illusion of being in the wild. In the morning, we chomped through a breakfast basket of hard-boiled eggs, warm croissants and rolls with jam, and yogurt topped with granola, while the dog that wandered over from the next-door neighbor’s house gave us the reassuring feeling of being kids camping in a backyard.

Rural Greene County is a three-hour journey from New York City, meaning it doesn’t lure as many weekend visitors as other parts of the Catskills, and therefore feels quieter and more remote. Driving on roads that twisted through the steeply rising mountains, we passed split-rail fences, stone churches, a lone woman walking a Saint Bernard. We spent a sunny morning at Mountain Top Arboretum, in Tannersville, where we were serenaded by birdsong as we followed meandering paths through shady spruce forests and fields of wildflowers.

Just down the road, we stopped at Kaaterskill Falls, one of the area’s most famous landmarks. The 260-foot-tall cascade has gradually become a victim of its own popularity, and I felt a little guilty wanting to visit when there are other perfectly good waterfalls nearby. But on a weekday in low season, it was relatively uncrowded, and from the viewing deck at the top of the falls, the scale and power of the scene was enough to make us gasp.

It seemed only right to end a day of trail-walking with a feast of carbs. We ate at Prospect—the restaurant at Scribner’s Catskill Lodge, a beautifully restored hotel in Hunter, another ski town—where the menu highlights the products of the region: smoked trout, cheeses from Hudson Valley farms. But I decided to hew Italian with an appetizer of toast piled with whipped ricotta and drizzled with spicy Calabrian honey, and an entrée of silky, savory cacio e pepe.

Urban Cowboy sits in a hollow within the Big Indian Wilderness Area, a large expanse of protected forest. After checking in, we walked down the vast, sloping lawn to a stony brook that pools into a swimming hole. I could feel the mountains rise around us, benign and protective.

That feeling of well-being continued throughout our stay. Our suite, at the top of a three-story chalet, had bedside sconces made from snowshoes—a reminder that the whole point of maximalism is that it’s fun. On the porch of the main lodge, we ate a superb meal of vegetarian small plates—slow-roasted cabbage, beer-battered shiitake mushrooms, and the best vegetable of all, french fries—to a soundtrack of Digable Planets and Ol’ Dirty Bastard. The convivial staff, whose first names we quickly learned, treated us like new friends, all while delivering on-point service.

Lyon Porter—who cofounded Urban Cowboy with his wife, Jersey Banks—told me that he spent much of his young adulthood in the Adirondacks and wanted to re-create the rustic luxury of the lodges there. “I want to see the Milky Way,” he said. “I want bears.” I found the best testimony to his and Banks’s vision on the faces of the other guests, which registered pure contentment.

Porter described Big Indian as the “doughnut hole” of the Catskills; it’s close to the intersection of three of the region’s four counties, and nothing is too far away. Indeed, a half-hour’s drive east brought us to Woodstock. The town’s history as a center for 1960s counterculture attracts tourists—even though the famous concert that shares its name took place farther south, in Bethel—and the shops on main street still display tie-dye and peace signs left over from the days when Bob Dylan and Van Morrison walked its streets.

But even the most stalwart hippie holdout can’t escape time’s arrow, and newcomers are creating subtle shifts. Over the course of a day’s visit, we ate fried avocado tacos by a burbling stream, courtesy of Tinker Taco Lab; Rosie DeVito’s perfectly salty-sweet chocolate-chip cookies, from her just-launched Overlook Bakery; a divine coconut charlotte cake made with the Filipino custard buko pandan at Harana Market, a new Asian grocery; and a thoroughly modern meal on the open terrace of a veggie-forward restaurant named Silvia.

There we consumed dish after savory dish—an heirloom tomato salad with za’atar, grilled halloumi with charred peppers and zhoug—but it’s the bread I remember best. A hot and magnificently fluffy pita was served alongside whipped butter and a pile of olives and radishes sprinkled with citrus zest, all of which felt so decadent it could have been dessert.

The more she learned about Catskills flora and fauna, the more she was eager to share her knowledge with transplants like herself. “I think people have an urge to go outside,” she said. “But they either don’t know where to go, or, if they get outside, they aren’t sure what they’re seeing.”

Silverman now leads nature walks with an emphasis on foraging, as well as workshops on cooking with wild plants and making natural cosmetics. Dressed in a khaki jumpsuit and a broad-brimmed hat, her silver hair in a long braid, she explained how hickory bark can be toasted and simmered with sugar to make syrup. She cut open a gall to show us the wasp larvae inside. She told us how to identify conifers by their needles: “If it hurts your hand, it’s a spruce.”

Like Silverman, Aaron Hicklin was inspired by early memories—in his case, of visits to small-town bookstores in his native England. He opened One Grand Books, in Narrowsburg, where the Delaware River divides New York State from Pennsylvania. A former magazine editor, Hicklin asks well-known figures—writer George Saunders, pop musician Phoebe Bridgers—to each recommend 10 books, and the shelves are organized around their picks.

“It’s like a very eclectic dinner party,” he explains, “where Tilda Swinton is sitting next to Ta-Nehisi Coates, who is sitting next to Laurie Anderson.” Hicklin has just opened a second branch of the shop in the town of Livingston Manor.

For Chicagoans Doug Doetsch and Susan Manning, the opening of their new Seminary Hill Orchard & Cidery, in Callicoon, is a homecoming: they are descended from generations of Callicoon families, and wanted to give back to the region. The result is a handsome modern building, partially made with wood from the now-demolished Tappan Zee Bridge, with spectacular views overlooking an orchard overlooking the Delaware River Valley.

Down the road, the cidery’s Boarding House occupies two classic clapboard buildings, a former hospital and a doctor’s office that Doetsch and Manning have turned into an enchanting place to tuck in after an evening of cider-fueled revelry. Tom and Anna Roberts of the Livingston Manor design team Homestedt styled the interiors with a simple Shaker aesthetic: a soothing palette of grays and olives, wooden accents, natural linens, and old prints from a book about New York apples.

On our last evening, we drove to the DeBruce, Kenoza Hall’s sister property, located on a quiet country road outside Livingston Manor. The hotel houses one of the best restaurants in the Catskills, also called the DeBruce, and we sat on the front porch, journeying through the nine-course tasting menu as twilight descended. The meal was what chef Eric Leveillee called “a weird trip inside my brain”: a purée of ramps, aerated cheddar, and peas; arancini filled with eel; langoustine wrapped in wild chamomile flowers.

Clad in Converse high-tops, our server, Connor Mikita, moved with an easy grace. We struck up a conversation with him, and he told us that he was the drummer in a group called the Nude Party. Mikita and his bandmates left North Carolina in 2018 and lived in a house owned by their manager in Livingston Manor. The hiatus from touring caused by the pandemic meant that they had spent a full four seasons there. Sure enough, he had fallen in love with the Catskills.

“I would definitely like to stay in and around this area,” he said. “Historically, it’s a special place. If you spend time here, you’ll feel a deep connection to the world.”

Eastwind Hotel & Bar: Scandi-chic A-frames and cabins in the ski town of Windham. Doubles from $279.

Kenoza Hall: A gracefully restored boarding house on quiet Kenoza Lake. Doubles from $449.

Urban Cowboy: A stylish retreat in the serene Big Indian Wilderness Area. Doubles from $275.

The DeBruce: Chef Eric Leveillee dreams up inventive dishes at this restaurant and hotel near Livingston Manor. Tasting menu $175.

Harana Market: This Asian market inWoodstock has a rotating to-go menu of Filipino dishes.

Overlook Bakery: Woodstock’s new bakery serves heavenly cakes, bars, and cookies.

Prospect: Order the homemade pasta at the restaurant of Scribner’s Catskill Lodge. Entrées $21–$65.

Silvia: Woodstock’s best restaurant focuses on fresh local vegetables. Entrées $26–$32.

Homestedt: This Livingston Manor store has stylish goods for indoors and out.

Maison Bergogne: A Narrowsburg antiques shop that feels like a cabinet of curiosities.

One Grand Books: Famous creatives curate the stock at this Narrowsburg store.

A version of this story first appeared in the November 2021 issue of Travel + Leisure under the headline Catskills Calling.