Beaches, golf courses, and fine wineries. One of Forbes’ Prettiest Towns in America, the village of Greenport New York retains its maritime history while providing exquisite modern accommodations. Founded as an authentic whaling town, Greenport transformed into a hub of the fishing industry and later, the railroad industry. After a period of success as an oystering center, Greenport remains a favorite destination for tourists.

With the Peconic River as an eye-catching background, tour Greenport’s boutiques, museums, restaurants, and old-fashioned general stores. Visit the Railroad museum of Long Island and East End Seaport Maritime Museum to immerse yourself in Greenport’s revolutionary past. Fill your belly with oysters and barbeque from Moonlight Mondays at Corey Creek, and rock out to live music and tapas at Sparkling Pointe.

Home to Kurt Vonnegut, Joseph Heller, John Steinbeck, and Nora Ephron, among others who worked or lived nearby, Greenport New York has also retained its artistic heritage. Now art galleries participating in Greenport’s gallery walk remain open late on the first Friday of each month from June to December, providing visitors with the opportunity to stroll through the village and appreciate local artwork.