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The first thing to know is that the Catskills aren't precisely defined. While “the Catskills” technically refers to the mountain range that spreads across upstate New York, the region isn't one with rigidly drawn borders. But when you say the Catskills — everyone knows what you mean. This is a quaint, rural stretch just a few hours north of New York City. And it's the place to go for hiking, for tiny, picturesque main streets, and for an overwhelming relief that you've finally escaped the congestion of the city that never sleeps.
I’ve been visiting the Catskills since childhood — for those born to New Yorkers of a certain age, it’s almost a part of our birthright. But the Catskills of past generations is not the Catskills of today. What was once littered with big resorts, the famous places where entertainers like Mel Brooks and Buddy Hackett made the Borscht Belt a household name, is now the purview of a stream of hip boutiques and cozy cocktail bars.
Yes, I feel confident in making the announcement: the Catskills are officially cool. After two decades of chain migration from the city and a stream of artists and restaurateurs from the hippest businesses in Brooklyn and Manhattan, this ain’t your father’s Catskills. So for one week this summer, I gassed up the rental and drove 150 miles, from the border of Pennsylvania to the edge of Massachusetts, to update my perspective on a region that’s constantly in flux.
First Stop: Callicoon
This was new to me. To me, the Catskills has always meant the area closer to the Hudson River, in the wilderness outside the towns of Woodstock and Saugerties. Here, at the far west end of Catskills, I found an even sleepier town. Callicoon: surrounded by woods and farms, with a downtown that yawns lazily along the abandoned railroad line. You can walk around the Delaware River, passing only the occasional groundhog or biker, breathing deep and taking in the sounds of the birds above. It feels a bit more isolated than some of the more popular Catskills towns, but for that reason it’s immensely peaceful. And the downtown has just enough attractions — restaurants, bars, to keep you busy as long as you stay.
Where to Stay: The Seminary Lodge Boarding House & Cidery keep a wonderfully Shaker-inspired boutique hotel just down the road from their organic, state of the art hard cidery. This is what brought me to Callicoon, and I tasted every cider in the collection between walks downtown and through the orchards and country roads. In the nearby town of Callicoon Center, another one of our favorites is Callicoon Hills, a boutique within an original house that dates back to 1905.
Where to eat: We have to call out the Seminary Lodge itself. Their Tasting Room (open Weds to Sun) offers a locally, sourced seasonal menu with views over the Delaware River Valley.
Next Up: Hudson River South
And now for something a little more cosmopolitan. Straddling the line in the public imagination (and tourism brochures) between the Catskills and the Hudson Valley, Kingston and Saugerties are among the most vibrant small towns upstate — close enough to the woods to feel natural and immersive, with enough going on to keep you busy eating and drinking between hikes. Kingston, with its claim as the original capital of New York State, has its share of history, but you may not notice it — places like Rough Draft Bar and Books make their home in the old stone buildings with little extra fanfare. Enjoy walking the waterfront and popping into boutiques.
Where to stay: At Hotel Kinsley, a historic boutique in central Kingston spread across four historic buildings, including a stately old bank and a pre-Revolutionary War cottage. Meanwhile, on a former rustic campground in Saugerties, Autocamp Catskills uses custom airstreams and luxe tents for a glamping experience we highly recommend. On your way here from Callicoon you'll likely pass right by the lovingly restored, sixties-era Starlite Motel.
Where to eat: Woodstock's just a ten minute drive from Autocamp Catskills, so if you've had your fill of grilling over the campfire, head off to the romantic Cucina for seasonal Italian or to Silvia, with their open kitchen and dedication to local meat and produce. We think it's worth the half hour drive to Gaskins in Germantown, where the owners planted their first upstate locale after city success at Gramercy Tavern, The Modern, Franny’s and Marlow & Sons.
Onward: Big Indian and Slide Mountain WildernessNow you're prepared for full, woodsy immersion. Where you’ll find some of the most popular hikes in the region. Giant Ledge is famous for the (five, actually) ledges that look out over the Catskills, and you can get the views with just a 3.2 mile hike, round-trip. Keep going and you’re on your way to the summit of the 3,720-foot Panther Mountain. Then there’s the hike up Slide Mountain, the tallest peak in the Catskills. There’s a range of difficulties, so find yourself a hiking app and sort by preference. On any side of the woods are a number of quaint towns with plenty of places to scrape off the mud and recharge.
Where to Stay: Urban Cowboy Catskills could hardly be a better hiker’s paradise. Set on expansive grounds, choose the inn or one of the freestanding cabins. Either way, you’ll have access to their restaurant and bar, perfect little swimming hole, and massive clawfoot tubs. A good option too if you’re looking for more upscale lodging that’s not too inconvenient for a ski trip at Hunter Mountain.
Where to eat: We love the bar and restaurant on-site at Urban Cowboy. And just ten minutes away is the Peekamoose Restaurant (open Thurs through Mon), a must-visit foodie destination in a restored farmhouse.
The Classic: The Hunter Mountain Area
To me the most quintessential Catskills escapes. Where rolling hills lead to trailheads in dense forests and picturesque main streets (like Tannersville’s straight line of brightly painted storefronts) that make up entire downtowns. Nearby North-South lake (for a small parking fee), is home to a few of our favorite, moderately challenging hikes to gorgeous vistas and rocky look-outs. Head to North Point or Artist's rock for a picnic on a blistering sunny plateau. In summer and on weekends, get here early. It's a favorite of many.
Where to stay: Hotel Lilien brings smart, contemporary design and a cozy restaurant and cocktail bar to its home in a 19th-century Victorian Mansion off the side of the road in Tannersville, while Eastwind Hotel & Bar has its own rural haven peppered with Scandinavian-inspired A-Frames and freestanding hammocks for guests.
Where to eat: Hotel Lilien is the "dining room" of the Catskills for a reason; with great comfort food headlined by their fried chicken sandwich. And a bucolic drive just 20 minutes away, the famous Phoenicia Diner (open Thurs through Tues) has been a Catskills mainstay since the early 80s — a classic diner with a vibe that's right out of Brooklyn.
Big Finish: Hudson River North
Finally, drive north along the Hudson for a couple towns with iconic names. Between Catskill and Hudson, it doesn’t get more emblematic of the region than this. Hudson’s made headlines over the years for the sheer number of new residents coming to make it their home — and the number of boutiques, antique stores, coffee shops and bars surely reflect that popularity. But what brought these people in the first place? Outdoor space, parks, and a location on the water that has some of the most gorgeous views you’ll find upstate.
Where to stay: The Amelia Hudson is a quietly chic and design-forward boutique on a residential street in Hudson that we adore. Or, drive about a half hour east and you’re at the border of Massachusetts and one of our favorite hotels: Little Cat Lodge, set under the Catamount Ski Mountain and founded by the restaurateurs behind several trendy spots in NYC.
Where to eat: Minutes away from Amelia Hudson, check out our three, seasonally-focused favorites — Feast & Floret, Wm. Farmer and Sons, and Rivertown Lodge Tavern — before taking a leisurely walk along the Hudson.
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Hero image: Seminary Lodge — Callicoon, New York