July 31, 2020

An Overnight Trip to The Hamptons

This overnight drive takes you from New York City out to the eastern tip of Long Island’s South Fork, aka The Hamptons. In summer these upscale beach towns are packed and accommodations are very expensive but, after Labor Day, the crowds thin out and prices drop, and it’s the best time to visit.

To help combat the spread of Covid-19, some venues below may be closed or by appointment or reservation only. Check opening hours before you go. Note that masks are required inside all venues except when you’re eating.

BookHampton. Photo courtesy of BookHampton

DAY ONE

First Stop: Great River, New York

The drive out to The Hamptons can be long and, if you’re going after work on a Friday, heavy on traffic. To break up the trip, stop half way at Bayard Cutting Arboretum (approx.1h) in the hamlet of Great River, New York. Created in 1887 by William Cutting, according to plans by Frederick Law Olmsted (of Central Park fame), the arboretum covers 690 acres of woodlands and planted areas. Many of the specimens in the pinetum date back to the original plantings of fir, spruce, pine and other evergreens. Rhododendrons and azaleas (in bloom May–June) border the walks and drives; wildflowers add blazes of color throughout the park.

Photo © Sierra Denise/iStock

Second Stop: Southampton, New York

If you’re hungry, drive straight to lunch at Shinnecock Lobster Factory (approx. 40-50 min). The simple roadside seafood joint is named after the Shinnecock Reservation on which it sits, home to Shinnecock Native Americans. From its window pour lobster rolls, seafood burgers (tuna, lobster, salmon, etc), and whole lobsters.

Southampton Books. Photo courtesy of Southampton Books

After lunch, drive 5-10 minutes to Southampton Books, a quaint indie bookstore with first editions (from The Cat in the Hat to Virginia Woolf’s Flush), contemporary fiction and nonfiction, stationery, games, and puzzles.

Parrish Art Museum. Photo by Bilyana Dimitrova, courtesy of Parrish Art Museum

Third Stop: Water Mill, New York

If you aren’t quite ready for a bite, drive directly from Bayard Cutting Arboretum to Parrish Art Museum (approx. 1h). The esteemed museum focuses on American art of the 19C and 20C, with major holdings of works by American Impressionist William Merrit Chase and the 20C realist Fairfield Porter, as well as by artists who have lived or worked in the area, including Jackson Pollock, April Gornik, Jane Freilicher, Roy Lichtenstein, Elizabeth Peyton and Dorothea Rockburne. You’ll find a regular program of changing exhibits, many featuring works from the permanent collection (advance, timed tickets required; book here).

Photo by Bridget Elkin, courtesy of Discover Long Island

From here, you can double back to Shinnecock Lobster Factory (10-15 min) or go around the corner to Duck Walk Vineyards. Taste four wines (Duck Walk’s include pinot grigio, riesling, cabernet sauvignon, pinot noir, pinot meunier, and malbec), and then enjoy a glass or bottle on the patio while listening to the live music that’s on every weekend.

Wölffer Estate Vineyard. Photo courtesy of Discover Long Island

Another winery option if you want to continue east is Wölffer Estate Vineyard in Sagaponack (15-20 min), best known for their rosé and cider (90-minute visits by reservation only; book here).

Sunset at the Hamptons beach. Photo © AlisonPerryPhotography/iStock

Check in to your hotel and spend the rest of the afternoon at the beach (beach passes are not required after Labor Day; if you’re in The Hamptons before Labor Day, ask your hotel).

LongHouse Reserve garden with Shin Sang Ho's glazed ceramic sculpture "Dream of Africa" (2004) . Photo courtesy of LongHouse Reserve

DAY TWO

First Stop: East Hampton

After breakfast and some beach time or a swim, drive to LongHouse Reserve, an extraordinary sculpture garden in East Hampton. Its 16 acres are home to permanent works by Sol LeWitt and Yoko Ono, as well as changing exhibitions (book advance tickets here).

The Studio, Pollock-Krasner House and Study Center. Film courtesy of Pollock-Krasner House and Study Center

Continue the contemporary art tour at nearby Pollock-Krasner House, the former home of artists Lee Krasner and Jackson Pollock, now part of Stony Brook University. See their house and studio and exhibitions by other modern artists (book advance tickets here for tours Thurs-Sun).

Cold lobster roll, The Lobster Roll. Photo courtesy of The Lobster Roll

Second Stop: Lunch in Montauk or in East Hampton

Drive 15 minutes east to Montauk for lunch at treasured The Lobster Roll, a retro beachfront eatery serving its namesake plus crab cakes, fish and chips, mussels, and chowders. Alternatively, pick up sandwiches from Springs General Store (down the street from Pollock-Krasner) and take them to the beach.

East Hampton has outposts of many shops and brands you’ll find in New York City. We recommend two excellent independent bookstores here: BookHampton (books set in Long Island’s East End and lots of contemporary and classic fiction and nonfiction, including a comprehensive selection of books on racial injustice in the US) and Harper’s Books, a shop/gallery specializing in rare and new art books.

Harper's Books Gallery during the exhibition "36 Paintings". Photo by Jenny Gorman, courtesy of Harper’s Books Gallery

Craft beer fans should stop in at Montauk Brewing, a favorite for their watermelon session ale (currently for to-go only, but patio and tasting room may reopen soon).

Photo © arturogi/iStock

Third Stop: Dinner in Westhampton Beach

For dinner on the way back to New York City stop in Westhampton Beach at tiny Aji Authentic Mexican Food, a favorite of Westhamponites for its delicious, well-priced tacos, quesadillas, and empanadas. Go for a seafood taco and a horchata and you’ll be blissed out. (Approx. 1h from East Hampton to Westhampton and 1.5-2h from Westhampton back to NYC.)

A Room at the Beach. Photo courtesy of A Room at the Beach

Where to Stay

A Room at the Beach: Ten beachy rooms in Bridgehampton, a few minutes from the town center. Sleep between Frette linens and rinse off beneath a rainfall showerhead after a dip in the pool or nearby beach. Lovely garden for lazing about in the shade of redwoods. Bikes available. From $510.

Daunt’s Albatross: Just outside of The Hamptons proper in more low-key Montauk is this family run motel. Its 23 simple, comfortable rooms all have mini fridges with microwaves. Hotel amenities include bike rentals and fitness classes included in room rate, outdoor saltwater pool, grills for guest use. Three blocks from the beach, this is one of the best deals in Montauk. From $109.

Hero image: Montauk Lighthouse. Photo by Alissa Rosenberg, courtesy of Discover Long Island

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Before hitting the road, be sure to check your tires’ air pressure and tread wear condition. Compare the tire pressure information on the tire sticker in your vehicle’s door or in your owner’s manual. If you need new tires, visit your local Michelin-certified dealers for the new Michelin ® Pilot ® Sport All-Season 4 tire, for the ultimate all-season performance, or the new Michelin® CrossClimate®2 tire, for luxury all-season driving.

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