Just east of the Old Fordham Mill, travelers find the village once known as Ketchabonack—though Westhampton has proved a much more memorable name. This residential town, along with neighboring Westhampton Beach and barrier beach community Westhampton Dunes, is familiarly referred to as “The First Hamptons,” and serves as the unofficial gateway to the East End. Historically, friendly Westhampton was the first of the Hamptons to begin renting out rooms, as well as the first Hampton to be accessed by the Long Island Rail Road; today, it remains welcoming, with a 40+ vendor Farmers’ Market every Saturday in the summer and lodgings for visitors that range from chain motels to charming, family-owned bed and breakfasts. Movies are shown every Monday during the summer on Westhampton Beach’s Great Lawn in cooperation with the local library, and the adjoining towns are home to a wealth of waterfront acreage along both Moriches Bay and the Atlantic Ocean.
If you plan to take a long weekend, be sure Monday night finds you at Starr Boggs’ famed Lobster Bake. Named for the chef-owner, this restaurant is known for their weekly feast, including an appetizer buffet, seafood bar, seasonal salads, and a wealth of other plates—all prelude to the lobster and steak main course—and at $75 for all you can eat, it is one of the Hamptons’ undisputed best dinner deals. The attractively intimate setting, with a screened-in porch and outdoor dining among landscaped gardens and waterfalls, doesn’t hurt, either. (6 Parlato Dr. 631.288.3500)
Another cozy dinner option, Buoy One, features classic Long Island fare, such as roasted local duck breast, in a cozy indoor-outdoor setting complete with a fireplace for breezy evenings and live music throughout the summer months. With a generous happy hour from 3 to 6 p.m. daily, there’s no reason not to stop in. Well, no reason except for their cracked-to-order clambakes, available for on-site pick-up or delivered and cooked at the location of your choice. (62 Montauk Hwy. 631.998.3808)
Considering a beachside clambake? Arrange a delivery to Pike’s Beach, 400 secluded feet of waterfront that is consistently less crowded than neighboring Cupsogue. White sand and clear water beckon, and sand wheelchairs make this beach unusually accessible for guests with mobility issues. The parking lot is home to an old-fashioned concession truck, and in addition to sunbathing and splashing around, the beach is fisherman-friendly. Surfers flock to this roomy break as well, and non-resident parking passes are available for a reasonable $25 daily fee. (765 Dune Rd. 631.283.6011)
For a more carefully curated waterfront experience, there’s the manicured beach, sprawling pool, and convenient boat slips at The Ocean Resort at Bath & Tennis. The salon and spa offer an ocean view massage, while the children’s play area allows parents to relax just a bit deeper as their kids frolic on a sandy playground. Tennis courts, presided over by nationally ranked senior singles and doubles player Doug Dean, offer active recreation, and of course, the luxurious hotel is a prime jumping-off point for exploring Westhampton and points east. (231 Dune Rd. 631.288.2500)
Once you’ve worked up a thirst on the tennis courts, it’s off to Margarita Grille, where outdoor seating and a two-sided fireplace are just the backdrop for some of the area’s best people-watching and cocktail-sipping. The playful menu of Mexi-merican fare, including “red, white and blue corn tacos,” is a comforting treat after a long day in the sun, and nothing washes it all down quite like a frosty frozen margarita with a Corona upended inside. (83 Main St. 631.288.5252)
For a more intimate, relaxing sip at the end of a long day, tuck into the cozy bar at The Patio at 54 Main, where a wide-ranging, affordable wine list complements the artful yet accessible signature cocktail selections. Nothing is more summery than their Fleur de Vies—peach-infused vodka with St. Germain and fresh grapefruit—and you can also indulge in an early taste of fall with their Fallin’ Pumpkin—organic pumpkin vodka with vanilla-spice cream and a cinnamon sugar rim—perfect for those first cooler nights in September. (54 Main St. 631.288.0100)