Long before giant hedges and oyster bars, Southampton was a Shinnecock Native American reservation and then a small whaling village. (It wasn’t until the introduction of the Long Island Railroad in the mid-19th century that New York’s elite swarmed in.) And it’s the vestiges of those pre-LIRR times, some tracing back to the 17th century, that make this beach town so special to me. As you walk along Hill Street toward town, signs mark the places that “the first carriage doctor” and the “first whale fishery in New England” once stood. If you’re lucky, you can even see some whales breaching near the horizon.
Southampton also boasts a robust artist history and community; the New York School of Abstract Expressionists most famously flocked there for artistic inspiration away from the overcrowded, dirty, concrete metropolis. So wipe away all preconceptions of “the Hamptons” and experience it as some of its earliest settlers intended: a seaside reprieve from the bustle of the city. Oh, and don’t let the end of summer scare you away. This is one beach town worth exploring all year round.
Eat Breakfast Burritos at La Hacienda
For the cheapest and arguably most delicious eats in town, head down Jagger Lane to La Hacienda. A father-and-daughter team run this authentic counter service spot, which accounts for the homey interior touches, like yellow walls decorated with small, whimsical designs of crescent moons and butterflies. Breakfast is served all day and includes such Mexican classics as huevos rancheros and machaca (scrambled eggs with shredded beef, onions, bell peppers, and tomatoes). For lunch, I love indulging in the overstuffed shrimp burrito, which includes all the usuals along with a spicy green “special sauce.” It also has excellent combos like a gordita and taco served with rice and beans for $9.95. 48 Jagger Lane
Stroll Down Southampton’s Beaches
You really can’t go wrong with any of the beaches along Gin Lane. Cooper’s Beach is the most well known in town, thanks to its inclusion on last year’s Top Ten Beaches in America list. For a more low-key experience, head to Halsey Beach; the white sand stretches far from the dunes to the ocean and it is never too crowded. If you’re looking to catch a surf break, sitting on the Little Plains sand feels exactly like Hawaii—the double sandbar creates the perfect conditions for long, white-washed rides. Seek out a Southampton staple, Miles, recognizable by his long brown hair freckled with bleached spots, as well as the slew of locals and fans swarming around him. He is a surfing legend, and any trip to Southampton should involve some type of interaction with him.
Slurp Clam Chowder at Silver’s
Silver’s feels trapped in time, and not just because of its no-cell-phone-devs rule. Renoir-esque paintings of ballet dancers cover the walls above mirrors that list the daily specials, floors are checkered black and white, and waiters still operate an old-timey cash register. The red brick building was first a cigar shop in 1905, but was taken over by the Wellins Family in 1923 and transformed into Silver’s. As soon as you sit down, a waiter, sometimes one of the Wellins brothers, will hand you crispy homemade garlic bread doused in olive oil and parsley. Skip the $65 lobster roll and instead order the most delicious Manhattan clam chowder of your life. The clams are large and the vegetables are cut in oversize chunks, perfect for a hearty meal. Owner Garrett Wellins has worked there since he was 8 years old and is coming up on his 65th birthday, though he’s thinking of selling—so get there fast. 15 Main Street
Refresh Your Wardrobe at Tenet
The shopping in Southampton can be a bit lackluster, due to its oversaturation of big-brand stores and knickknack-y stops. Tenet stands out from the rest because of its impeccable curation of established and emerging designers. It stocks well-known labels like Isabel Marant and Iro, and always presents pieces unlike what you see in the chicest department stores. Tenet also sells nonclothing goods like Le Labo candles and Oliver Peoples sunglasses in its adjacent storefront. 91 Main Street
Go Back in Time at Pelletreau Silver Shop
Open since 1696, this silver shop is the longest-running business in the East End. It first operated as a dry goods store, then Francis Pelletreau took it over in 1717 as a space for his blacksmith and metalwork shop. Today, master jeweler Eric Messin showcases his designs, following the Pelletreau tradition, in this small Main Street cabin. The shop is distinguished from the other stores on the street because of its naturally aged shingles and a simple brick chimney atop the gambrel roof. Messin will happily give you a tour of the historic remnants from 1696 in the building; he also offers silversmithing classes. 80 North Main Street
Get Cultured at Parrish Art Museum
The East End has always been a refuge for artists seeking inspiration from the landscape and open air. Many Abstract Expressionists, among them Jackson Pollock, Lee Krasner, and Helen Frakenthaler, established permanent residencies there, which greatly impacted their respective artistic styles. The Parrish’s iconic Herzog & de Meuron building aims to convey the look of these artists’ Long Island studios. The museum’s industrial, horizontal appearance stands out against the flowing, open landscape it sits on. Until October 15, explore the East End’s artistic history through the exhibition predominantly focusing on James Brooks and Alan Shields. 279 Montauk Highway
Catch the Sunset at Munn’s Point
Bike along Meadow Lane to spy some of the most spectacular houses on Long Island, and stop to watch the sunset at Munn’s Point while you’re at it. Much more wholesome than the fake tans strutting down Main Street, Munn’s is the perfect spot to appreciate the natural beauty of the East End. Catch glimpses of migratory birds flocking, as well as horseshoe crabs sprawling throughout the bay. The greenish hue of the bay brilliantly picks up the fiery colors in the sky. Opposite 880 Meadow Lane
Finish the Day at Tutto Il Giorno
To feast on northern Italian specialties in a most beautiful garden, reserve a table at Tutto Il Giorno. The space is a total expression of the founders’ backgrounds: Gianpaolo de Felice, a pilot from Italy, designed the menu to reflect his nonna’s cooking, and Gabby Karan de Felice took inspiration from her mom Donna Karan’s bohemian style. The backyard has beige pebbles underfeet, and large white umbrellas and string lights hang over the heads of diners. Order the burrata with halved cherry tomatoes, which are so sweet they almost taste like candy. Finish off with the branzino in parchment paper, cooked with fresh summer vegetables and a light olive oil and lemon dressing, or the paccheri, a Neapolitan-style slow-cooked beef ragu served over wide house-made noodles. 56 Nugent Street