The village of Catskill doesn’t seem particularlyCatskilly.
The England-born Cole began painting this part of upstate New York in the 1820s.
Caleb photographed graffiti that early visitors had carved at the cliff’s edge.
Bethel Woods, site of the 1969 Woodstock music festival.Tara Donne
We had the site to ourselves, and the scene felt primordial and peaceful.
The rustic-glam Chatwal Lodge opened in Bethel in spring 2022.)
Eastwind’s most beguiling element is hidden from view.
From left: Kaaterskill Falls, one of the best-known natural landmarks in the Catskills; Eastwind Hotel & Bar provides guests with binoculars for viewing scenery and wildlife.Tara Donne
Just down the road, we stopped at Kaaterskill Falls, one of the area’s most famous landmarks.
I could feel the mountains rise around us, benign and protective.
It seemed only right to end a day of trail-walking with a feast of carbs.
From left: A guest room at Urban Cowboy, a resort in the Big Indian Wilderness Area; a dessert of melon, cocoa, and vanilla sorbet at the DeBruce restaurant, near Livingston Manor.Tara Donne
On Instagram, the guests looked Gen-Z and playful, whereas I am middle-aged and reserved.
But any anxiety was dispelled the moment Caleb and I walked into the main lodge.
Urban Cowboy sits in a hollow within the Big Indian Wilderness Area, a large expanse of protected forest.
From left: Picnic provisions at Main Street Farm, a grocery and sandwich shop in Livingston Manor; the home of 19th-century landscape painter Thomas Cole, in the village of Catskill.Tara Donne
I could feel the mountains rise around us, benign and protective.
That feeling of well-being continued throughout our stay.
“I want to see the Milky Way,” he said.
From left: Dover sole at Kenoza Hall’s French-inspired restaurant; Juliette Hermant at her Narrowsburg shop, Maison Bergogne.Tara Donne
“I want bears.”
Indeed, a half-hour’s drive east brought us to Woodstock.
We were accompanied by Laura Chavez Silverman, a self-taught naturalist who created the Outside Institute in 2017.
“I think people have an urge to go outside,” she said.
She cut open a gall to show us the wasp larvae inside.
He opened One Grand Books, in Narrowsburg, where the Delaware River divides New York State from Pennsylvania.
Hicklin opened a second branch of the shop in the town of Livingston Manor.
The sight made my heart race.
Clad in Converse high-tops, our server, Connor Mikita, moved with an easy grace.
The hiatus from touring because of 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.”
Kenoza Hall: A gracefully restored boarding house on quiet Kenoza Lake.Doubles from $349.
Urban Cowboy: A stylish retreat in the serene Big Indian Wilderness Area.Doubles from $275.
Harana Market: This Asian market in Woodstock has a rotating to-go menu of Filipino dishes.
Main Street Farm: Great sandwiches and gourmet provisions in Livingston Manor.
Overlook Bakery: This Woodstock bakery serves heavenly cakes, bars, and cookies.
Prospect: Order the homemade pasta at the restaurant of Scribner’s Catskill Lodge.Entrees $24$65.
Silvia: Woodstock’s best restaurant focuses on fresh local vegetables.Entrees $30$34.
Outside Institute: Laura Chavez Silverman leads nature walks in the region.
Thomas Cole National Historic Site: The Catskill home of the Hudson River School painter.
Where to Shop
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 ofTravel + Leisureunder the headlineCatskills Calling.
