The North Fork of Long Island—located 75 miles east of New York City—is known for its still-sleepy waterside charm, pebbly beaches, verdant farmland, and wealth of vineyards, many of which are family-run. What’s more, over the last few years, a new and refreshed crop of chic boutique hotels and seafood-savvy eateries have only added to the timeless allure of what’s already shaping up to be one of the East End’s most lively seasons. And, rather notably, sans the summertime crowds and traffic you’ll find in the Hamptons.
Where to Eat
Last spring, Andrea Tese, a local photographer and conservationist, opened her first restaurant Minnow in New Suffolk. Offering only line or trap-caught fish coupled with water views, expect raw bar classics (such as local Peeko oysters), a bountiful organic salad niçoise, and a delightful spaghetti con crudo. Across the street, the venerable Legends recently swapped hands, and in a fun twist, will also serve Tese’s updated menu of crowd-pleasers.
Down the road, James Beard-winning chef Francois Payard has a duo of eateries: Southold Social has a spacious back patio serving Montauk black sea bass and summer truffle polenta while Southold General is ideal for coffee, quiche, and flakey croissants. Back in 2020, New York-based chef John Fraser took over the North Fork Table & Inn, where oysters, salads, and meats are sourced from nearby purveyors and a food truck serves lobster rolls and pop-up smash burgers. Nearby, the seafood-leaning Little Fish offers ceviches and spicy tuna tartare taquitos. Afterwards, stroll to Kenney’s Beach and watch the sun fade over the Long Island Sound.
The hip-and-happening 55-room Sound View Inn, opened in 2017, also houses the Halyard: an airy, A-framed eatery with pan-seared scallops, poached cod, and prime water views. Later, slip into the cozy Piano Bar for chilled martinis and Baby Grand selections (there’s often karaoke too). Further down the road, Duryea’s Orient Point is fashionable for a late lunch (think lobster salad, whole-roasted fish, and bottles of everything), people-watching, and rotating DJs. You can also arrive by boat—slips are first come, first serve.
Set in a former bait-and-tackle shop in Greenport, Little Creek Oysters pairs its namesake with water views (you can also shuck your own). Or stock up on sandwiches at Salumeria Sarto, where come evening, an osteria has rotating dinners by owner-chef Frank DeCarlo, formerly of NYC’s Peasant. Golden oldies like 1943 Pizza serve tasty wood-fired pies and salads, while the speakeasy-esque Brix and Rye shakes fancy cocktails and Lucharitos remains packed for buzzy margaritas and fish tacos. Finally, after a long time in the making, the revamped 150-plus-year-old Claudio’s has finally returned to its seafood dining roots. Picnic tables at Southold Fish Market are ideal for the freshest of fresh clams and oysters.
Impromptu picnic? Here you’ll find local farm stands aplenty: Sang Lee Farms has organic produce and delicious dips (don’t miss the scallion ginger with crudité) while Seps Farm always has a fresh bounty. In Cutchogue, 8 Hands Farm has a market with fresh eggs, heritage breed meats, lard soaps, and a food truck with breakfast and lunch. Save room for dessert: Magic Fountain scoops throwback ice cream flavors, while Briermere Pies continues its legendary reign (opt for the fruit-forward blueberry cream). For a pick-me-up, Aldo’s offers small-batch coffee drinks.
Where to Drink
Over the last 10 years or so, the North Fork—with its 60 wineries—has enjoyed a creative, critically-touted evolution. Start at the biodynamic, sustainable, and family-run Macari Vineyards, whose 500 acres feature a handsome tasting room and covered deck where top-end red blend flights (or a bottle of the cult-favorite ‘Horses’ pet-nat) are paired with charcuterie and cheese. Nearby, Meadowlark, Macari’s dreamy new sister property, pours small-batch wines in a pastoral setting.
Meanwhile, other classics like Lenz Winery, founded in the late 1970s, often couples its tastings with live music, while the 127-acre Paumanok Vineyards has a turn-of-the-century barn for sipping. The family-owned McCall Wines also pours an array of flights (including a Robert Parker-endorsed Sauvignon Blanc) to pair with its popular grass-fed burger night.
Italian-born Claudia Purita and her daughter are behind One Woman Winery, a sustainable, low-impact vineyard with outdoor seating while RGNY Wine nods to its Mexican heritage with sparkling selections in minimalist bottles and canned wines (don’t skip the handmade chocolates either). Speaking of bubbles, for 20 years, the always-crowded Sparkling Pointe has been focused solely on offering an array of fizzy concoctions. Greenport Harbour Brewery has a lively happy hour with briny delights courtesy of Little Ram Oysters—a beloved female-owned and operated business—alongside its namesake suds and frozen Palomas.
And to curate your own collection, drop by OneKourt Studio, a well-curated wine shop stocking several local varieties alongside niche global labels and indie spirits.
What to Do
On North Fork’s most easterly tip, Orient—a sleepy hamlet once frequented by the poet Walt Whitman—smacks of Montauk before the Manhattan crowds descended. The expanse of Orient Beach State Park is lovely for biking, kayaking, and swimming (or simply enjoying the shoreline views of Gardiner’s Bay). In Southold, Goldman’s Inlet runs from the beach to a tranquil saltwater pond, and remains a peaceful spot to view a thriving Osprey population. Come evening, the Custer Institute and Observatory (established in 1927) houses a 22-foot steel dome and powerful Zerochromat telescope, giving you a peek into the far celestial ethers.
Take a day trip to Shelter Island (a short ferry ride ushers you and your car to and fro). Fuel up with made-from-scratch artisan bagels and cold brew at the ’80s-inspired Eccentric Bagel. Then, head to the Nature Conservatory’s Mashomack Nature Preserve, whose trail network traverses over 2,000 acres of tidal creeks, mature oak woodlands, and freshwater marshes.
For shopping in Greenport, the boho Lido hawks kaftans, sundresses, and vintage furnishings; while Rica Bath and Body stocks linens and natural made-in-Brooklyn bath salts. For beachy reads, drop by Burton’s Books; and, if you’re itching to feel like a kid again, ride the antique Greenport Carousel. In Southold, White Flower Farmhouse carries vintage furnishings, while across the street, White Flower showcases fresh blooms, garden tools, and candles. About a mile away, the Morning Sun Shop stocks farm produce, locally-made sea salts, beach towels, and chic sarongs.
Where to Stay
Last summer, the shiny new Silver Sands (first established in 1957) reopened to great fanfare. An array of chic-and-cheery rooms, 33 in total, extends to longer-stay, multi-bedroom beach houses with vintage furnishings, reading nooks, and screened-in porches. The best seats at Eddie’s—the property’s al fresco eatery—are at the bar that comes artfully wrapped around a century-old oak tree. New York City chef Ryan Hardy (also of Charlie Bird and Pasquale Jones) is behind the refined seafood (oysters are plucked on-site) and wood-fired Neapolitan pies, while Nookies offers elevated diner staples: farm eggs, mussels with fregola, and a root beer float. With 45 acres, you have all the pastimes, too: sunbathing, swimming (on a private beach), bicycle cruising, outdoor showering, cocktail fire pit gathering, and just to round things out, some bocce ball.
Last year, the owners of Croteaux Vineyards—a well-trodden Southold winery known for its rosé—opened this new 20-room property along the Long Island Sound. Set on three rolling acres, coastal-colored, water-facing rooms feature fireplaces and spa-like bathrooms. A glass-encased lobby has cocktails and snacks alongside a chic sundries shop. Enjoy the saltwater pool, take a spin on the beach cruisers, or visit the barn-style cottage for birdhouse-making and tie-dye classes. Of course, the real magic happens at sundown on the grassy lawn, ideal for local wine and hushed conversation—and later, s’mores.
Two years ago, The Shoals opened just off Main Road in Southold. A two-story, cedar-shingled sprawl comes outfitted with 20 spacious suites and private balconies. A soothing palette decorated with subtle light blue tones, jute rugs, and oakwood tones seems to blend seamlessly into the marina-meets-bay surroundings. There are also plenty of boat slips outside to drop in and idle a while—after all, this summer’s food truck is run by Alewife Brewery, and is hosting an unfussy seafood-focused menu alongside wine and cocktails.