Settled in the early 1700s, Sag Harbor’s historical bona fides are many. It served as a stage for the American Revolutionary War, with one of its hills becoming a battleground that saw British casualties and the capture of 90 British soldiers. Long Island’s first custom house was built in Sag Harbor, and the harbor itself played a role in the War of 1812. And so on. As the first port of entry of the U.S., Sag Harbor emerged as a hotbed of social vitality and thriving interaction where various kinds of people — soldiers, seamen, merchants, and artistic types — freely mixed. John Steinbeck was perhaps the village’s most famous literary resident of the 20th century; novelist E.L. Doctorow (Ragtime) and Pulitzer Prize-winning playwright Lanford Wilson also lived here. Sag Harbor’s well-respected nonprofit Bay Street Theater, founded in 1991, continues to nurture the town’s arts-and-letters reputation, as do the readings at Canio’s Books, which has been around since 1980.

No two ways about it: Sag Harbor has a thriving Main Street, and several dining venues come up again and again among the locals. Wölffer Kitchen bills itself and its sibling in Amagansett as “the first winery-owned restaurants on the East End,” and this spot has won devotees for its seasonal cuisine, community vibe, and selection of wines, ciders, and spirits. Page at 63 Main prides itself on local oysters and its sautéed veal piccata, as well as its more virtuous vegan vegetable grain bowl. BLT chef Laurent Tourondel has the low-key LT Burger, and the Neapolitan pies at the year-old Sag Pizza have been greeted with open arms. With Sag Harbor known for charm and taste, it’s small wonder that Main Street has at least two homewares shops that win raves: Fishers Home Furnishings and In Home.