It all started with raspberry cream pie. Homemade buttery blind-baked crust and a cloud of whipped cream filling, topped with a thick layer of ruby-red raspberry preserves. If you don’t arrive early, the daily lot will likely be sold out at Briermere Farms, a whitewashed seasonal farm stand on the outskirts of Riverhead, New York, where Long Island divides into its twin North and South forks.
To head southeast is to make your way through the posh “East End”—from Southampton and Watermill to East Hampton and Amagansett—before landing in Montauk, a bygone fishing village that’s largely traded maritime charm for trendy beach clubs and social-media cachet.
My family settled seasonally some 50 years ago in Westhampton Beach, a low-key hideout just south of Riverhead. Idyllic childhood summers were spent shuttling between camp and the beach, playing golf and tennis with a horde of cousins and friends. But every now and then, my mom and I would break free from the routine and pop up to the North Fork to requisition a Briermere pie for dinner. Driving east on Route 25, a mix of salt and earthen breeze would waft through the windows as we passed miles of cornfields, vineyards, and wildflower farms. It became a cherished tradition of sorts—a pastoral palate cleanser from the familiar (at times, predictable) Hamptons rhythm.
The ritual came full-circle in 2020, when I became a mother. My husband and I took our then-seven-month-old on a day trip to Orient Point, stopping at an animal farm in Mattituck and enjoying a leisurely waterfront lunch in Greenport. Now, with three kids in tow, North Fork visits have become a summer highlight. Our list of mainstays has grown as stylish boutiques, enterprising wineries, and contemporary restaurants have become ever-more commonplace in an evolving landscape.
Here are the places we return to year after year:
Between the whitewashed stone walls, idyllic waterfront setting, and trendy acoustic soundtrack, it’s as if you’ve transported to a European beach club at the North Fork counterpart to Montauk’s über-scene-y mainstay, where lobster rolls and crispy fries are the order.
Seasonal fruits and vegetables are showcased daily at this whitewashed two-story farmhouse, famed for its fresh-baked cream– and meringue–based fruit pies.
Littles can while away an entire day feeding the farm animals, climbing the jungle gyms, and running amuck in the hedge maze. Apple-picking and hayrides make Harbes an equally fun-filled off-season escape, but thankfully sugar-crusted cider donuts are a year-round takeaway from the onsite bakery/farm stand.
Sleek, contemporary architecture juxtapose a wild, rocky promontory at this 20-room luxury hideout, just a few minute’s drive from downtown Greenport. You’ll catch a well-heeled clientele lounging by the glass-enclosed pool and convening for Friday happy hour sips with live music. Families will appreciate quiet surf at the private beach, plus twice-monthly activations with Petite North Fork during summer.
Bread and Butter Market, Riverhead
Homemade gelato, artisanal coffee, freshly-baked breads, and gourmet groceries are just some of the reasons to pitstop early at this elevated roadside market on Route 25. (And yes, you need that bag of chocolate chip cookies for the drive.)
Orient Beach State Park, Orient
The $10 entrance fee a worthy investment in order to park your beach chair on 45,000 feet of rocky frontage on Gardiner’s Bay. The raw natural beauty, peaceful surrounding marshlands, and horizon as far as the eye can see imbue “end of the Earth” solitude.
Claudio’s Waterfront & Saylor Beach House, Greenport
Nestled in the charming cobblestone village of Greenport, this buzzy restaurant draws a large weekend following, owing to a robust live music lineup and crowd-pleasing menu (don’t sleep on locally sourced clams in the half shell).
William Ris Gallery, Jamesport
There’s a distinct Long Island sensibility in the original contemporary works on view at this 1960s-era gallery, which champions East Coast female artists, including Carol C. Young and Susan Giblin.
Antique garden accents—the kind you’d spy in high-end design magazines—line the walls of this tiny shop on Southold’s Main Road, which also sells locally grown, fresh-cut stems.
Claudio’s new sister restaurant, which occupies an adjacent pier in Greenport Harbor, pairs citrus-hued accents with a signature Lemon Freeze cocktail. Come for the elevated Mediterranean dishes (fried zucchini chips with tzatziki; chimichurri-coated skirt steak), stay for the picture-perfect sunset snaps.
Maritime terroir is at the core of North Fork viticulture, and Bedell has a 40-year winemaking history that showcases this unique regional style. Reserve a cellar tour or drop in for a tasting flight on the scenic patio, overlooking the vines.
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