If adorable was a town it would be this tiny Catskills hamlet on the Delaware water gap. More remote than the Hudson Valley, but getting less sleepy all the time thanks to a thriving creative community, head here if far-flung (but not desolate) is your kryptonite.

Clockwise From Top Left: The Elder Statesman Turtleneck; The DeBruce; SLVERLAKE Jeans; Proenza Schouler Combat Boots; Givenchy Duffel

STAY: Sullivan County’s most stylish gathering spot award goes to The DeBruce. You’ll dig the lodge’s take on rustic luxury (at its’ finest), like a dramatic glass dining room (view porn) and the out-of-this-world nine-course menu, all foraged from local organic sources.

DON’T MISS: Lifestyle boutique game on lock: Swing by Nest, the brainchild of a former Vogue design director and W alum — you can stock up on, say, mid-century-adjacent furniture designs, cowhide boots from Norway, or even a handmade Dhurrie rug. Next, point your credit card in the direction of Sunny’s Pop; Owned by Mark Ruffalo’s wife, her namesake concept shop is filled with golden rays, but also sustainable, waste-conscious merch. We’re ‘stanning over Yoke’s body oils and a retro silk-screened dartboard.

WHAT TO WEAR: If après-ski was après-hike. Mood: Super-soft cashmere sweater, worn-in SLVERLAKE jeans, and Proenza’s Clueless-in-the-Catskills green and yellow plaid combat boots ready to runway-out the nearest country lane.


This vibrant mini-city, less than two hours from NYC, has eclipsed Hudson to become the area’s buzziest destination.

Clockwise From Top Left: Chloe Jacket; Hotel Kinsley; Fontana Milano BagIsabel Marant PantsChloe Boots

STAY: Designed by Robert McKinley, king of effortlessly cool interiors (he’s the dude-genius behind the Surf Lodge), Hotel Kinsley is close to all the retail action. Spread across four restored historic buildings, look for in-room fireplaces, gram-ready art, and a dining experience from It-restaurateur Taavo Somer.

DON’T MISS: For a wine bar you wish you lived next to, head to Brunette. Guarantee you’ll be charmed by the clean-cozy Parisian aesthetic, small plates (get the jalapeno hot dog if you want some heat!), and, of course, quality vino worth getting drunk on.

WHAT TO WEAR: If Brooklyn had a rural twin. Color palette: light brown and olive. Go for haute hunter feels by tucking Isabel Marant’s cargo pants into Chloe’s British-aristocrat-meets-runway rainboots.


Once a manufacturing hub, it’s now less grit, more Gagosian. You can thank Dia Beacon for the status-quo shake-up — since its’ debut in 2003, the 160,000 square-foot museum has drawn the City’s art cognoscenti and influencer crowd in exponential (but still manageable) droves.

Clockwise From Top Left: Chloe Sweater; The Roundhouse; Alaïa Leggings; MM6 Maison Margiela Boots; Celine Sunglasses

STAY: The old Matteawan Manufacturing company, an OG textile factory, has been masterfully transformed into The Roundhouse, an ambitious hotel, restaurant, and event space overlooking a waterfall even TLC would like. A savvy meld of bucolic countryscape and urban industrial, the complex is the de rigueur neighborhood nexus for homegrown talent and international creatives scouting for the new Wolfgang Tillmans or Yayoi Kusama.

DON’T MISS: You’ll definitely break a sweat on Breakneck Ridge Trail, a rigorous three-hour climbing/hiking loop in the East Hudson Highlands. But hey, pain is beauty — the pinch-me views are #unfiltered level.

WHAT TO WEAR: Gallerist who hikes. That means cozy basics with editorial verve. Throw on Chloe’s alpaca sweater with a poncho silhouette and Alaïa velvet leggings that say ‘I’m casual’ from far away, and ‘yes, I’m wearing Alaïa upstate’ when you come a little closer.


Just over the New York boarder in Western Massachusetts you’ll find this hopping hub, which has been experiencing a cultural renaissance courtesy of MASS MoCA’s (legit, the biggest contemporary art museum in America) launch in 1999.

Clockwise From Top Left: Tourists Welcome; Frame Jeans; Christian Louboutin Ankle Boots

STAY: Tourists Welcome came to town last year, offering exceptional Insta-bait in the form of its’ minimal, thoughtful design (informed by the iconic American motor lodge), culinary programming in a farmhouse dating from 1813, as well as its proximity to the region’s stunning woodland trails and riverbanks. The lack of pretension doesn’t hurt, either.

DON’T MISS: You might need two days to get through the sprawling converted factory building complex that is MASS MoCA. The nine James Turrell installations that make up his ‘Into the Light’ exhibition are a trippy and even transformational Must (that capital M wasn’t a mistake).

WHAT TO WEAR: From the shearling on your Louboutins to the feather on your fedora, you’ll be ready to pose on the trail, at the gallery, or by the fire.