Puritan settlers, a famous witchcraft trial, and meticulous regulation are all part of an East Hampton legacy of do’s and don’ts. The size of homes and the number of beach parking passes are sharply limited. A hilarious assessment by the late “Little” Edie Bouvier Beale, the eccentric subject of the campy documentary Grey Gardens (1976), is well known for its quirky but deadly accuracy: “They can get you in East Hampton for wearing red shoes on a Thursday.” Established in 1891, the Maidstone Club is so picky about its membership that even George Plimpton and Diana Ross were denied membership (even though the latter’s billionaire husband was a member). The scenic lagoon of Georgica Pond played summer host to President Bill Clinton (at the home of Steven Spielberg, no less), and its residents have included Martha Stewart and Calvin Klein. If rigorous attention to maintaining the flavor of East Hampton is perhaps off-putting to visitors, locals reap the benefits of sky-high property values and its shingle-style architectural history.

Point one: Nick & Tony’s on Main Street is the East Hampton dining institution. For those not in the know, when The New York Times six years ago offered that the most coveted real estate in the Hamptons was a choice table in the eatery’s front room, the message was indisputable. 1770 House Restaurant, East Hampton Grill, and the Palm are also must-do’s on Main Street. For burgers, baked clams, steamers, and lobster rolls, a more casual gastronomic experience can be had on the pretty patio at Bostwick’s Chowder House. International brands are represented by Ralph Lauren (and Lauren’s daughter’s confectionery, Dylan’s Candy Bar), Lululemon, J. Crew, Vilebrequin, and Audemars Piguet (the watchmaker); some shops are open only for the season.