Generally referred to as simply "the Hamptons," the South Fork actually consists of a group of towns, not all of which actually end in "Hampton" and each with its own flavor. Regardless of name, though, this is where the rich and famous spend their summers, and with good reason: Some of the most gorgeous land in New York State -- and some of the best beaches in the world -- is here. Ever since the railroad was built out to Southampton in 1870, people have been hooked on the South Fork.
While winters are relatively quiet, the summer season brings crushing crowds and a flashy nightclub scene. A drive along Route 27 requires immense patience, so it's worthwhile figuring out what kind of experience you seek so that there's not a lot of backtracking. Eastport is a tiny hamlet filled with antiques shops; Westhampton has tree-lined streets and Victorian mansions; Southampton boasts old money, huge estates, and chic stores; East Hampton is the trendy, new-money capital of Long Island (Jerry Seinfeld, Billy Joel, and Martha Stewart have homes here); Sag Harbor is a gorgeous town on the water where even the dry cleaner has antique irons in the window; Amagansett and Bridgehampton are cute little towns; and laid-back Montauk relishes its position at the island's tip -- set apart from the more exclusive villages, it's also a big draw for fishermen and surfers.