The North Fork of Long Island: Best Hotels, Restaurants, and Wineries

Pool area at the Sounview Greenport — (Image credit: The Sound View Greenport)

Last spring, the folks at Bentley kindly suggested I take their new Bentley Continental GT Speed out for a spin—an offer I couldn't refuse considering the car is quite literally fit for a Queen (and still serves as the official state car for Queen Elizabeth II). There's a convertible option, alongside a lot of other treat-yourself moments, like a neck warmer and automated massaging seats, plus, they're working towards a more sustainable future with their Beyond 100 strategy.

But I couldn't just take a Bentley anywhere, so I planned a weekend away to one of my favorite destinations, the North Fork, to support some of my favorite local places— the area's powerhouse assortment of women-owned businesses. Here's where to stay and what to do on a road trip to The East End.

Filled with charming shops, a thriving art, and culinary scene, and let’s not forget plenty of wine, the North Fork of Long Island, New York, is a chill summer or fall getaway studded with rich nautical history. Once a major whaling port and a central hub for the fishing industry, this is the destination to feast on shellfish and sip rosé all day. But don’t get it twisted: The East End is not a hub for beach clubs and white parties like its southern neighbor, The Hamptons. It’s a place to unwind, mingle with the locals, and savor the fresh sea breeze.

Where To Stay

One of the rooms at the Soundview in Greenport

Situated directly on the beachfront of the Long Island Sound, The Sound View is a boutique hotel slightly removed from the hubbub of North Fork's main drag in Greenport. Under new ownership, the hotel has undergone extensive renovations from its former motel state, modeling its minimalist beachfront rooms off of classic North Fork homes— all with magical sunset views.

Cool off in the open waters or at the pool, and dine at the Halyard—Sound View's local seafood restaurant, preparing dishes with ingredients directly from North Fork farmers and fishermen. In the evening, pull a seat up to the outdoor Low Tide bar to enjoy live music, cocktails, and fire pit roasted s'mores.

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What To Do: Day 1

Take a morning walk on the beach, then head to yoga at Sang Lee Farms — owned by Lucy and her partner William—for a slow-flow class or a guided meditation. On weekends, stroll through the Greenport Farmers' Market and gather local produce like farm-fresh eggs, homemade jams, and delicious North Fork wines. For an excellent selection of vintage treasures, pop into The Times Vintage, a father-daughter-owned shop on Main Street on Greenport's main drag. Comb through classic and retro designer pieces, accessories, housewares, and vinyl records.

Bentley's new blue convertible — Beep, beep! from Bentley's Continental GT.

For beautiful handmade caftans and home decor, visit LIDO, owned by Heidi Kelso Swing, Manhattan-based music, fashion, and entertainment media executive who brought her world travels back to Greenport. Take a cruise by the 100-year-old Jess Owen Carousel House in the middle of town and end the day with a drive to Lavender by the Bay, a family-owned and operated lavender farm located in the nearby village of East Marion.

What To Do: Day 2

The pool area at the Sound View in Greenport

If the weather is nice, grab a swimsuit, slather on some SPF, and rent a few paddleboards from One Love Beach, owned by water sport-loving couple Blake and Chris Dowling, and set off and explore the Bay.

Afterward, it's time to indulge in the region's award-winning wineries. Check out the intimate tasting room at Claudia Purita's sustainable One Woman Wines & Vineyard. Purita meticulously planted each vine with thirteen wines featured on the tasting menu, ranging from warm weather favorites like rosé and chardonnay to red varietals like merlot and pinot noir. Prefer beer over vino? Stop by Greenport Harbor Brewery, and sample one of their sought-after seasonal beers. Hang out for the live music and catch one of their special events, like their adorable dog-dock diving competition, put together by their female-led community division.

Where To Eat

Like their wine, North Forkers know a thing or two about their beans. At North Fork Roasting Co., grab an artisan brewed cup of coffee and an acai bowl topped with homemade granola, fruit, coconut, cacao nibs, and chia seeds. Drop in at Love Lane Kitchen in Mattituck for lunch and order a lobster roll with a side of garlic herb fries.

Oyster happy hour at Little Creek Oyster Farm & Market—located in a picturesque Bait & Tackle shack on Greenport’s marina front—is a must. For more oysters, check out Yennicot Oysters, where oyster-woman Meg and her family have farmed oysters in the tidal flats for over a century. For French fare like a charcuterie board and steak tartare, take yourself to dinner at Demarchelier Bistro, a newly opened restaurant by Emily Demarchelier— whose parents owned and ran the former Demarchelier outpost on the Upper East Side of Manhattan.

Sara Holzman is the Style Director at Marie Claire, where she oversees fashion coverage spanning seasonal trends, celebrity style, designers, Fashion Month, and shopping. With more than a decade of experience in fashion media, she has held roles at Condé Nast’s Lucky and Self and contributed style and travel coverage to Equinox’s Furthermore. A graduate of the Missouri School of Journalism, Sara is based in New York City, where she writes about fashion through both an industry and personal lens, including the realities of getting dressed as a working mom. Follow her on Instagram at @sarajonewyork.