Sagaponack’s earliest settlers in the mid-17th century were potato farmers, and some of the estates of today’s billionaires were constructed on former potato farms. The Sagaponack Historic District, which nabbed a spot on the National Register of Historic Places, is a source of local pride — and participation. Fully 131 buildings and sites uphold the standard; they include the post office, 17th-century homes, 18th- century residences in the Federal and Greek Revival styles, plus bungalows and examples of the boxy, anti-Victorian Foursquare style that appeared after the turn of the 20th century. Most contributing buildings on the Historic District’s inventory be found on or near Main Street; for example, Kurt Vonnegut owned the home at 620 Main, which was built around 1740.

Despite its coveted real estate, Sagaponack never really let go of its rural character. As in other Hamptons villages and hamlets, Montauk Highway represents the main commercial thoroughfare, though this stretch is sedate compared to the action in Sag Harbor, East Hampton, and Bridgehampton. Most of what you need can be found here and on Main Street, which runs perpendicular to Montauk Highway. Loaves & Fishes does prepared food well — blue fish salad, brownie pudding, along with shrimp, scallop, and feta stew. South of Loaves & Fishes is Pike Farms and the Sagaponack farmers market (cauliflower, beets, snap beans, berries). And Wölffer Estate Vineyard (entrance on Sagg Road) boasts several award-winning labels.