A quieter Hamptons escape on the North Fork | Field Trip

If the idea of a getaway to the Hamptons makes you (or your wallet) cringe, consider the ritzy beach communities’ lower-key neighbor, the North Fork.

With coastlines along the Gardiners Bay and Long Island Sound, you’ll find the same lovely scenery and maritime-village vibes with fewer crowds and less pressure — especially in the preseason. Spring is a great time to wander the North Fork and its neighbor, Shelter Island, a quick 10-minute ferry ride away and home to a a Cape May–connected hotel brand.

Sustainable wineries, entrenched artisans, icy oysters, and empty beaches await, just four hours from Philly. Start the car.

Before boarding the North Ferry in Greenport to Shelter Island, pop into Pip’s Cafe & Provisions around the corner from the terminal. The spot is bright and charming, with blonde wood, blue tile, and butcher-roll menus advertising all-day breakfast. The egg-and-cheese comes on a fluffy house-baked milk bun, and the pastry case dazzles with chocolate croissants, carrot cake-inspired muffins, and bomboloni in rotating flavors like strawberry-guava, churro, and vanilla-glazed apple topped with bacon crumbles.

📍 218 Main St., Greenport, N.Y. 11944

A local connection in the Hamptons, the historic Pridwin Hotel and Cottages (est. 1927) on Shelter Island gets its preppy swagger from Cape Resorts, the hospitality group behind Congress Hall and Beach Plum Farm in Cape May. Fans of those properties will feel right at home in the 33 rooms and 16 cottages, finished with fireplaces, shiplap, and rattan, on Crescent Beach. Complimentary bikes, firepits, and pickleball courts complete the Americana summer-camp vibe, even in the spring.

📍 81 Shore Rd., Shelter Island, N.Y. 11964

Even if the water’s still too cold for swimming, you can still get out on it. The Pridwin stocks stand-up paddleboards and kayaks for guests on a first come, first served basis. Roughly a three-mile paddle from the resort takes you to the Mashomack Preserve, a 2,350-acre sanctuary of protected marsh and woodlands with an 11-mile shoreline. Glide into coves and scoot down tidal creeks while spotting the ospreys, red-tailed hawks, woodpeckers, and 200 other bird species that call this stretch of the Peconic Estuary home.

📍 79 S. Ferry Rd., Shelter Island, N.Y. 11964

Zaftig teapots, fluted pie plates, vases veined like watermelon rinds come out of the kiln at Greenport Pottery, a beloved studio that has anchored the North Fork’s creative community since 1981. Located near Southold Fish Market, the shop is open regular hours on the weekends and by appointment during the week.

📍 64725 NY-25, Southold, N.Y. 11971

If you drive to Orient Point, at the tip of the North Fork, and hook around, you’ll wind up on a spaghetti-strand road bordered by water on both sides. Take it as far as it goes, to the parking lot at Orient Beach State Park, and get ready for one of the most epic beach walks in Long Island. This state-protected finger of beach, wetlands, and marine forest stretches into Gardiners Bay. You can walk along the shore or interior trails all the way to Long Beach Bar Lighthouse, originally built in 1870 and affectionately nicknamed "Bug Light."

📍 40000 Main Rd., Orient, N.Y. 11957

On Friday nights, locals gather at One Woman Wines in Southold, a 20-year community touchstone just west of Greenport, for live jazz and glasses of cabernet franc in the expanded tasting room. The sustainable winery is a mother-daughter operation run by Claudia and Gabriella Purita, producing grüner veltliner, gewürztraminer, pinot noir, and several other award-winning wines. If you can’t make it on a Friday night, they do tastings every day except Tuesday, and reservations are essential.

📍 5195 Old North Rd., Southold, N.Y. 11971

With a nautical, window-wrapped dining room cantilevered over Long Island Sound, Halyard makes the most of its location. If the weather cooperates, sit on the deck while the sunset draws lilac and paints tangerine streaks across the sky. The menu is seafood-forward (raw oysters, baked cherrystones, swordfish schnitzel, Montauk tilefish with mushrooms from nearby Mattituck), and the wine list includes 14 North Fork pours.

📍 58775 County Rd. 48, Greenport, N.Y. 11944