A Shore Thing: Tall bluffs in parts of Montauk create a striking shoreline, where wooden steps lead down to the beach. The only oceanfront bluffs on Long Island, they’re a remnant of long-ago glaciers.
The End: Drive until the pavement stops on Long Island, and there it is—the iconic Montauk Point Lighthouse at the easternmost point of New York.
Dives & Taverns:A view from the Main Street sidewalk into Montauk’s Shagwong Tavern, open since 1927; during our visit, a handwritten sign in the window reads, “Piano player wanted, must have knowledge of opening clams.”
A concession stand at Amagansett’s Atlantic Avenue Beach
Oceanfront Oasis: Named for the wild sea grass that grows in the dunes, the 96-room Marram sits beachfront in Montauk with a restaurant, yoga sessions, and central courtyards in the sand.
About 100 miles east of Manhattan and with no skyscrapers in sight, the Hamptons and Montauk are famously a summer-fall escape by the shore—picturesque, super stylish, and salty all at once.
Fishing Village: Montauk Harbor still fills with seafaring boats, returning with fresh-catch fare.
Three clam dishes—chowder, on the half-shell, and clams casino—at The Dock.
Island Art: A large Andy Warhol piece in “The Art of Food” exhibit in one of Parrish Art Museum’s modern shed-style galleries in Water Mill; the permanent collection focuses on artists who created works on Long Island.
Sag Harbor is an old whaling hub with quaint streets of shops, marinas, and historic homes. (Above) Near Il Capuccino Ristorante and Via Coquina boutique on Madison Street
At the Montauket for sunset on the deck overlooking Fort Pond Sound.
Inside, sunlight streams in while the Lynn Blue Band plays rock and soul hits for the crowd around the bar.
Silhouettes in the stairwell, enamel paint on the banister, and all-around classic nautical style at the 67-room Baron’s Cove in Sag Harbor.
Baron’s Cove overlooks the Sag Harbor Cove Yacht Club.
French onion soup and a Guinness for a cozy lunch at Rowdy Hall, Amagansett.
Historic maps of Long Island at the Restaurant at Baron’s Cove in Sag Harbor.
A window of lamps, lights, and boats inside English Country Home, Bridgehampton.
The vines and gates at the entrance to 1818 Collective, a design shop inside a historic home in Sag Harbor.
Contemporary art on the 14-acre grounds and meadows of Parrish Art Museum in Water Mill.
Vineyard rows near the tasting room at Channing Daughters Winery in Bridge-hamptom.
In Montauk, a beach of rocks tumbled by waves and interesting sand colors, ranging from beige and amber to deep plum.
Follow Montauk Highway to its oceanfront end for a weekend that’s both rustic and refined
