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Hamptons Guide: Summer Living in the Hamptons

Your guide to the perfect summer getaway in the Hamptons.

Summer in the Hamptons. It’s the escape we all dream about: heading to the beach, lounging around the pool and grabbing some great East End grub. Add to that the ongoing art shows that the Hamptons are famous for, outdoor yoga, hiking and other family-oriented activities, and you have a vacation playground that’s nothing short of spectacular. Just pack your patience – traffic can get a bit crazy, and reservations are a must at the most popular restaurants and inns. With ever-changing Covid guidelines, be sure to check websites and schedules when making reservations.

Summer Dining

The pandemic has made outdoor dining a permanent fixture at many of the Hampton’s restaurants. Indoor dining is also available, and exciting vineyard pop-ups have added to the varied local and chef-driven options. 

A worthy stop if heading to Montauk or a concert at The Stephen Talkhouse, all-American Main Street Tavern has indoor and outdoor seating and small-town hominess. Menu ingredients are locally sourced and find their way into small bites and comfort food faves like steak sandwiches, lobster rolls and not-to-be-missed chicken wings. The garden area is a seductive spot for a classic cocktail or glass of wine from a list smartly curated by boutique wine shop Parcelle.

A favorite among New York City foodies, Kissaki is all about elegant sushi and distinctive sake. Décor matches cuisine quality with clean lines, stylish Japanese minimalism and creative expression. In addition to unusual futomaki, beautifully presented omakase sets and creative nigiri, Kissaki’s chiffon cakes are a welcome and unusual surprise. Socially aware seating includes indoor podlike areas and a chic open-air patio.

Dining at Calissa is like a quick trip to the Greek isles. Whitewashed and airy, the restaurant offers a menu of all-time Greek menu hits. An expansive garden area is beautifully lit and creates a perpetual “on vacation” feel. To keep your spirits high, there’s a program of DJ and live music throughout the summer.

Popular Highway Restaurant & Bar serves seasonally inspired dishes with ingredients from nearby farms and purveyors. The New American menu includes faves such as miso-glazed salmon, Peking duck and spit-roasted chicken with sourdough stuffing; all finished with Highway’s sinful chocolate chip cookies.

Hidden behind Jobs Lane’s many shops, Bamboo is a fun spot for affordable Asian fusion cuisine. Outdoor umbrella-shaded seating is the setting for the restaurant’s popular happy hour. A choice of sakes and an extensive menu of sushi and sashimi are complemented by popular dishes like Bang Bang chicken, Mongolian beef and chicken lemongrass dumplings.

Chef Jean-Georges Vongerichten brings Michelin-starred dining to the Hamptons at the Topping Rose House. The pretty Jean-Georges dining room and patio are coveted spots for seasonal dishes along with the chef’s signature tuna tartare and black truffle pizza.

A solution for those who can never make up their mind, Union Sushi & Steak offers an elegant setting for steaks and inventive sushi creations. Local ingredients feature on the menu, including duck egg rolls with Long Island duck confit. A must-order, the Union Roll is an unexpectedly harmonious combination of lobster and avocado, topped with marinated skirt steak, eel sauce and yuzu mayo. Evenings are enhanced with live piano accompaniment. 

Main Street Tavern Garden | WhereTraveler
Main Street Tavern Garden (©Ronen Lev)

Shopping and the Arts

Shopping is more than a casual pastime in the style-obsessed Hamptons. One-of-a-kind boutiques mix with NYC shops, with most concentrated in Southampton, East Hampton and Sag Harbor. Southampton’s Farmers and Artisan Market take place each Sunday at Agawam Park with a variety of crafts and foods from local artisans.

Mounted during the pandemic to encourage outdoor art exploration,  "Field of Dreams" concludes this summer at The Parrish Art Museum. Through Labor Day, "Everything That Wasn’t White: Lonnie Holley at the Elaine de Kooning House" is an exhibit of 35 artworks created during the noted artist’s stay in East Hampton.

LongHouse Reserve invites you on a personal exploration of the 16-acre reserve and sculpture garden where notable pieces by Yoko Ono, Buckminster Fuller and Willem de Kooning are on view. Southampton Arts Center offers a second outdoor sculpture garden this summer with an exceptional exhibit entitled "WHIMSY," a collection of oversized pieces by Louise Bourgeois, Larry Rivers and others.

After a disastrous fire that nearly consumed the building, Sag Harbor Cinema returns refreshed with a schedule of indie films. Visitors to the town can also buy tickets for Bay Street Theater’s varied schedule of theater, comedy and music. 

Farmer's Market | WhereTraveler
Farmer's Market (©Nataliya Vaitkevich)

Inn Life

A Hamptons tradition, Southampton Inn is casual and family-friendly, offering 90 guest rooms, each with slightly different decorations. The inn’s restaurant, Claude, is popular for its signature weekend brunch. Bikes and helmets are available for rental, and the inn runs a shuttle to Cooper’s Beach.

The Baker House 1650 is Hampton’s history at its most elegant. A striking bed and breakfast with architecture inspired by 17th-century Cotswolds, the Baker House was originally built in 1648 as a residence for a sea captain. Later a tavern and now a B&B, Baker House provides a mix of refinement and comfort with indulgent amenities, including an onsite spa.

If you’re longing for an island getaway, The Ram’s Head Inn is the right place for you. Take your vehicle on the ferry from Sag Harbor, dock your boat or hop the inn’s complimentary shuttle and go car-less. The 17-room waterside inn is distinguished by its relaxed yet well-appointed accommodations and polished service. Not staying overnight? You can buy a “Grass Pass” for a day and enjoy the inn’s spa, oyster tastings, yoga and hula hoop classes and sunset music.

Spa at the Ram's Head Inn New York | WhereTraveler
(Courtesy Spa at the Ram's Head Inn)

The Great Outdoors

Surfing may not be the first thing that comes to mind when you think of the Hamptons, but it’s quite serious on the East End. Suit up and buy your board at Flying Point Surf & Sport. Then head to Dutch Plains in Montauk or sign up for Flying Point’s Surf School to enjoy the area’s remarkable waves.

Prefer to stay on land? Plan an oceanside hike at Walking Dunes, where you can climb the dunes and wander among cranberry bogs or stay inland amid woodlands and marshy areas in Shelter Island’s Mashomack Preserve. Be sure to wear long pants to avoid ticks and mosquito bites.

For a milder walk through the vineyards of the East End, visit the annual Wine Stand pop-up at Wölffer Estate with its weekend wine, charcuterie and outdoor music evenings. 

Hamptons Beaches New York | WhereTraveler
Wetlands (©Ted Mochen/Pixabay)