The Great Escape: Summer Out of the City

We adore our hometown. New York, New York—the city so nice, they named it twice.

But sometimes distance does indeed make the heart grow fonder.

And there’s no better time of year than early summer to venture out of the five boroughs for a quick getaway. Throw that Summer Friday on your calendar, pack your weekender, hit the road (or Amtrak), and enjoy a short escape from the hustle and bustle. Here’s where we’re heading—and what we’re wearing, of course.

NORTH FORK

Brave the journey through Long Island traffic because a weekend of winery-hopping, coastal eats, and laid-back energy on the North Fork is worth it. Spend your days exploring a handful of the many, many vineyards and dozens of breweries and craft distilleries in the area. When your day calls for some sustenance, dine at The Halyard in Greenport for stunning waterfront views, or Little Creek Oyster Farm & Market to enjoy shuck-your-own oysters. For a luxe-but-quaint stay, opt for The Menhaden, or if you can get lucky, snag one of the four rooms offered at the Rose Hill Inn—a luxe bed and breakfast on a 22-acre winery.

For your weekend out East, chic-but-cool is the move—like a silk halter worn with a wide-leg flowing pant, or a linen midi dress.

MONTAUK

For more of an energetic coastal affair, opt for the other Fork and head to Montauk instead. Your home base? Check into the ever-popular Gurney’s Montauk, or the luxury boutique surf resort Marram.

Summer’s start is a bustling time in Montauk. The last weekend in June brings “Art on the Green,” a showcase hosted by the Montauk Artists Association. Fuel your art-filled venture with the freshest seafood—head to Duryea’s (infamous lobster cobb salad, please!), Crow’s Nest, or Navy Beach. When you need to slow down, indulge in a treatment from The Seawater Spa or take in the sunset on the hill at The Montauket.

Achieve that just-got-off-the-beach look with a draped sarong skirt or floaty slip dress and—when you’re wearing shoes—a flat sandal.

HUDSON VALLEY

Venture north to explore the Hudson Valley, a region known for its vast, vibrant arts scene—and we’re just in time for this year’s annual Upstate Art Weekend. Running from June 25 through June 29, this self-guided event connects over 160 artists, galleries, museums, and creative spaces through exhibitions, open studios, public installations, and more.

Aside from the art world, the Hudson Valley boasts a diverse food scene, bookstores aplenty, antique shops, and charming stays.

If we had to choose just one destination, the city of Hudson checks all our boxes. Opt for a chic stay at the relatively new Pocketbook Hudson Hotel and Baths, or The Wick, a re-purposed 1860s candle factory. As for dining—foodies, rejoice. Hudson is home to some of the most delightful meals this editor has ever indulged in. Our perfect night? Dinner at feast & floret for farm-to-table Italian, followed by a nightcap at the Maker Hotel’s cocktail bar, Lounge. Look the part with a smart top—think an oversized blazer or cowl neck silk blouse—with dark denim and a kitten heel.

NEWPORT, RHODE ISLAND

Set off for the Ocean State and find Newport—a coastal escape chockfull of gilded-age mansions, scenic cliff walks, and the freshest seafood. And June is the absolute perfect time to visit. Weekly Newport International Polo Series events kick off with the first Saturday of the month, and the 30^th annual Newport Flower Show— with stunning floral exhibits, garden displays, and boutique shopping at the historic Rosecliff mansion—begins on June 19.

Other items on our weekend itinerary: touring the historic Newport Mansions, rolls at Luke’s Lobster, walking the famous 3.5-mile Cliff Walk, sunset drinks at Castle Hill’s Lawn Terrace, dinner at White Horse Tavern, and a stay at The Vanderbilt.

For an outfit that mimics Newport’s vibe, lean on your more-preppy pieces. Reach for a long skirt and coordinating peplum top, or a lightweight striped button-up. Don’t forget to combat the sea breeze with an extra layer.

NANTUCKET

For the quintessential New England weekend, make your destination Nantucket. A ferry ride away from Cape Cod, the serene island is marked by classic cobblestone streets, charming cottages, and bright hydrangeas as far as the eye can see.

Your stay can go one of two ways: Opt for the lively, trendy Faraway hotel downtown, or reside on the secluded waterfront at The Wauwinet. Food options on the island almost feel endless. Asian fusion at The Nautilus, caviar-topped lobster rolls from Cru, oysters from 167 Raw, crab and corn pasta at Straight Wharf—our mouths are already watering. Aside from eating, eating, and more eating, spend time at the annual Nantucket Film Festival through June 22.

What to wear? Crisp coordinates. Pair a poplin button-up and midi skirt, or opt for a linen matching set.

We will always count our lucky stars to live in magical New York City, but sometimes a quick escape is just what the soul needs.