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Northwest of Manhattan, the series of tiny hamlets that make up the Catskills is a place of untamed wilderness and historical intrigue. The Catskills Park and Forest Preserve incorporate 700,000 acres, and over 200,000 acres of that are protected land, kept forever wild. In the mid-19th century, artists came here to capture the area’s rural beauty, drawing New Yorkers out of their urban dwellings to the pine-covered, fairytale-like mountain range. Home to the Borscht Belt in the 1920s until the ’70s, a series of now-abandoned resorts where comedians like Joan Rivers came to perform, the area has long been a welcoming place for visitors of all backgrounds and cultures. Today it’s a haven for skiers and artists, and anyone with a sense of adventure and a need for respite from city life.
To get to the Catskills, drive just over two hours north on I-87 from New York City.
Leave New York City mid-morning to arrive in Woodstock for lunch at Shindig, a sunny spot serving organic comfort food, craft beer, cider, and wine. Ingredients are sourced from local purveyors, and breakfast, including delectable baked goods, is served until 3 p.m. Or, try the all-vegan Garden Cafe.
Once you’ve fueled up, head to Belleayre Mountain, with ski trails for all skill levels. Belleayre hosts a festival in fall, and in the summer you can swim at Belleayre Beach, take a gondola ride, or go for a hike. Après ski (or hike, or swim), dine at Peekamoose Restaurant and Tap Room in Phoenicia, a converted farmhouse with exposed beams and a patio with a fire pit where you can have cocktails and toast marshmallows. Hearty meat dishes are their specialty. As an alternative, try Ze Windham Wine Bar.
Enjoy a craft cocktail, beer, or wine, at the intimate but fully-stocked bar at the boutique Eastwind Hotel. Though seating around the bar is minimal, there is plenty of room to relax in the lounge area, including around a fireplace or in front of a chessboard. Down the road you’ll find the casual Mulligan’s Pub at the Windham Country Club.
Start the day with breakfast at Robin Hood Diner in the town of Livingston Manor, a classic diner with home-cooked breakfast (and often a line out the door). Gear up for over 300 miles of trails to hike in Catskill Park, with summits and fire towers offering unparalleled views of the region in every season. The vast wilderness includes wetlands, lakes, forests, and meadows. For your post-hike lunch, Main Street Farm in Livingston Manor is a rustic cafe with an emphasis on local ingredients. Menu items include inventive sandwiches, salads, and soups. Upward Brewing Company nearby also serves lunch.
Enjoy a boozy afternoon at the Prohibition Distillery. The restored, late 1920s firehouse now produces small batches of gin, vodka, and whiskey. Tours are also offered, or you can just hang out in the tasting room.
Have dinner (served Thursday through Sunday) at Northern Farmhouse Pasta in Roscoe, whose pasta dishes are made with 100% New York-grown wheat. Vegetables are fresh and seasonal, and the ravioli is their signature dish. You can also dine outdoors at gourmet pizza spot, The Kaatskeller. Liven up the evening by heading to The Arnold House in Livingston Manor, whose tavern hosts karaoke and occasional live music and bonfires. They also have pool tables and a jukebox.
For breakfast on your last day, your best bet is the highly-rated yet simple breakfast at the Phoenicia Diner. Specialties include corned beef hash and chicken and waffles. A good backup breakfast option: The Pines. Take an easy jaunt to Kaaterskill Falls, the subject of paintings and folklore, or get a massage at the luxurious Windham Spa before returning to fast-paced city life.
For lunch, try the quaint Bear and Fox Provisions for something tasty in their coffee shop/grocery store. The charming spot in Tannersville has rotating dishes like soups, avocado toast, and creative lattes. Or dine at Phoenicia Market and Deli.
Spend the afternoon perusing art, collectibles, and housewares you can only find in the Catskills. Your choices include the vintage wonderland, Mystery Spot, in Phoenicia, with records, costume jewelry, and other fun finds; Reveries in Woodstock, a paradise for anyone nostalgic for the 1960s; and Nest in Narrowsburg, filled with eclectic wares; among many other shops. Art galleries and museums include the Woodstock Artists Association & Museum; the Center for Photography at Woodstock where Janis Joplin, Joan Baez, and Bob Dylan performed when it was a coffee house; the enormous Emerson Kaleidoscope housed in a grain silo; and so much more.
Before you hit the road, stop in for a burger or fondue at Last Chance Cheese and Antiques Cafe. Browse or buy something from their vintage candy selection as a souvenir before heading home.
WHERE TO STAY
You’re spoiled for choice when it comes to lodging in the Catskills. Some of our favorites include The Arnold House in Livingston Manor, an inn with just 10 guestrooms plus a two-bedroom lakehouse. The casual-chic property on Shandelee Mountain has a spa on-site and a tavern with live entertainment in the summer. The Eastwind is a new addition to Windham; the former hunting and fishing lodge has a small spa, bar and lounge, and A-frame cabins so you can wake up to gorgeous mountain views. The retro Kate’s Lazy Meadow (owned by Kate Pierson of the B-52’s) is a ’50s motel; rooms have vintage kitchens, and outside there is a communal fire pit.
WHEN TO GO
The Catskills are truly a year-round destination. Many escape here in the winter for skiing or cozying up in the lodge. Take in views while hiking or biking here in the fall, or relive the summers of decades past.