A drive through the Hamptons is a 50-mile trek through one of the most affluent, cosmo-politan and internationally-renowned regions of the nation. The Hamptons scenery ranges from dramatic seascapes to charming streetscapes. Streets are lined with stores (anything from antique shops to boutiques to upscale retailers), historic buildings and homes that vary from modest to stately to ultra-modern. Furthermore, you’ll see a num-ber of unique landmarks.
To begin your journey, turn south off Sunrise Highway/ Route 27 to Highway 61 and on to Eastport Manor Road and drive into the heart of Eastport with its antique shops and the Shrine of Our Lady of the Island. Continue east on Montauk Highway/Route 27A to Westhampton Beach, a ca-sual sandals and shorts spot with rows of retail shops. You may encounter a fair at the Village Green or catch a show at the Westhampton Beach Performing Arts Center, lo-cated inside a vintage theater.
Follow Main Street east to Montauk Highway through historic East Quoque and Quoque (pronounced “qwog”). These appealing communities contain historic homes, miles of ocean beaches and antique shops. East Quogue boasts the wide lawns, bandstand and wishing well of Hamlet Green, and lovely Tiana Beach — a picnicking spot that is open to the public.
Next, you’ll encounter the village of Hampton Bays, known for its parks, beaches, leisure boating community and the second largest fishing fleet in New York State. Nightlife centers around highly-popular pubs and clubs. As you leave the village, you’ll pass through Canoe Place, where the Canoe Place Inn has stood since 1750. Local sights include Shinnecock Inlet, cre-ated by the Hurricane of 1938; the Shinnecock Canal, in year-round operation since 1938, and Ponquogue Beach, a fa-vorite of everyone from surfers to swimmers.
Heading east on Mon-tauk Highway, you’ll pass the Shinnecock Indian Reserva-tion and its log cabin-style museum on the right, followed by Southampton’s famous estate section, and then Southampton Village. Founded by New England settlers in 1640, Southampton mesmer-izes the traveler with upscale shops, restaurants and pubs, the Parrish Art Museum (fea-turing a sculpture garden) and Conscience Point Historic Site and Nature Walk, at which a boulder marks the spot where English settlers made their first landfall.
As you leave Southampton, Montauk Highway becomes Route 27. Duck Walk Vineyards will appear on your left as you enter Water Mill, another quintessential Hamptons community. Water Mill is home to Long Island’s oldest-operating water-powered mill, built in 1644, and a museum where visitors can see howa mill works and see how weaving and quilting are done .
Next stop: Bridgehampton, featuring antique shopping and eateries, Mecox Beach on the Atlantic, and the Bridgehampton Polo Club. The Bridgehampton Historical Society’s historic buildings are open to the public .
Make a left at the monument at the eastern end of Bridgehampton’s Main Street, turning onto Sag Harbor Turnpike. Sag Harbor’s 19th century whaling landmarks include the Custom House, which was the nation’s first port of entry beginning in 1790; the Sag Harbor Whaling Museum and the Old Whaler’s Church; and a museum dedicated to the village’s fire department, the oldest in New York State. The Chamber of Commerce, located inside a windmill on Sag Harbor’s Long Wharf, offers free walking maps for interested visitors.