Once an edge-of-the-world escape for artists and surfers, Montauk has become a favorite for sun-seeking New Yorkers, Europeans and beach bums alike. The sandy, salt-washed town has a distinctly East Coast sensibility, which, from May to September, mixes with a high-vibe beach party atmosphere imported by the young Manhattanites and destination travelers who flock there. Despite its sequestered location at Long Island’s windswept terminus, Montauk can feel like the center of the world, especially on summer Fridays with an Aperol Spritz in hand and the weekend ahead.
At Surf Lodge, a funky beach property with a hipster motel feel, a sprawling deck overlooks Fort Pond and is perpetually packed with beautiful people. Sunday afternoons at the property are spent lingering over brunches of lobster rolls and egg sandwiches, while on weekend evenings, a summer concert series (featuring everyone from James Murphy and St. Lucia to Kimbra and Gary Clark Jr.) draws masses that inaugurate the night with spritzes and platters of oysters and little neck clams. The advantage of booking a room at Surf Lodge: After a late night, you can drop directly into bed and do it all over again the next day.
If Surf Lodge is where the twenty-somethings descend for revelry, The Crow’s Nest (and its beautifully appointed inn and cottages) is where thirty-somethings and beyond gather for lively but lower-key sunset cocktails and meandering Mediterranean meals. Boho décor and rough-hewn surfaces are well-paired with local fluke crudo, oysters, marinated olives and Aperol Spritzes. As evening edges in and aperitivo gives way to dinner, the terrace provides a quiet respite for blue crab tagliatelle, Montauk scallops and another round of drinks. Repeat around the fire pits with a side of marshmallows and s’mores.
For those seeking a more secluded respite, the recently refreshed Gurney’s Montauk Resort is worth a visit. Situated on a stunning private beach, the hotel maintains a feeling of quiet luxury sometimes lost in busier Hamptons hubs. The main bar, the Regent Cocktail Club, overlooks the beach and fills with well-heeled guests as the beach club filters out and the tide rises to meet the dunes. Classic cocktails and Aperol Spritzes are the perfect companion to the sunset hour before moving on to Scarpetta, a beachy outpost of the iconic Italian restaurant in Manhattan.
For a more local spot, head over to Swallow East, a seafood joint near the Montauk docks where trawlers depart as the sun rises, returning just in time for happy hour with their catch. The Swallow’s best seats are along the deck, where live music plays to a sun-kissed crowd winding down from a day along the shore. If the weekend becomes a long one, happy hour from Monday to Thursday is worth dropping in on.
But if a true escape from the sometimes painfully cool South Fork scene is what you’re looking for, The Montauket has been around since 1959 and remains entirely loyal to its humble beach shack origins. Here, you’d be just as likely to observe a beer-hoisting local as you might a rosé-swilling East Hamptonite, but the bar’s no-nonsense appeal has a democratizing effect on all who laze on the patio waiting for sunset with a pile of fried shrimp and scallop fritters. Order an Aperol Spritz and, in the spirit of summer Friday benevolence, offer to buy your neighbor one, too.
Surf Lodge | 183 Edgemere St.
The scene: Chic city folks in town for the weekend to mingle with artsy hipsters in town for the al fresco concert series.
Go for: Fresh Long Island seafood, spritzes and the advantage of being able to drop straight into your hotel bed after a night of dancing.
The Crow’s Nest | 4 Old West Lake Dr.
The scene: Stylish restaurant and bar, for a crowd seeking a quiet but very cool evening outside the party scene.
Go for: Food reminiscent of the Italian Riviera, nightly s’more service and cocktail-hour spritzes.
Gurney’s Montauk Resort | 290 Old Montauk Highway
The scene: A well-heeled hotel set seeking a bit of Manhattan on the South Fork.
Go for: A variety of settings, including a beach club for day drinking, a café for brunch, a cocktail club for before and after dinner and the legendary Scarpetta for refined Italian fare.
Swallow East | 474 West Lake Dr.
The scene: Weekend live music is the soundtrack to a crowd of post-beach cocktailers. Plenty of deck seating and a great view of the water.
Go for: Seafood fresh from the dock, shared plates and ice-cold Aperol Spritzes.
The Montauket | 88 Firestone Rd.
The scene: A true locals’ bar, The Montauket is a diamond in the rough where both locals and weekend revelers gather to gaze out over Fort Pond Bay at sunset.
Go for: Sunset on the patio, with a mound of fried seafood and a spritz.