First inhabited by the Pequot native Americans, Southold has a long history of colonization, starting with the Puritans in 1640. Theirs was the first European settlement on Long Island; Dutch settlers followed shortly thereafter. The earliest Puritan inhabitants were stringently religious, but the area loosened up later in the 17th century. Real discord was sowed not by religion but by nationality, as the British and the Dutch both agitated for control of the Suffolk County settlement. The British prevailed; indeed, the name Southold is said to derive from a similarly named town in England’s own Suffolk County. The rise of Southold’s vacation appeal can be credited to two things: advances in technology, which connected the town and hamlet to the Long Island Railroad, and the area’s unique geography. Southold town’s singular mix of land and water — a thick-and-thin landmass that terminates at Orient Point to the east — is stunningly scenic, luring artists who celebrate the light bouncing off the various bodies of water.

Southold hamlet is in something of a transition, as the low-key, neighborly place is seeing an escalation of Hamptons-like dollars and properties. The evolving retail scene includes Einstein Square, named for the famous scientist, who frequently visited and shopped in the hamlet during a summer spent on the North Folk in 1939. The area has a multitude of vineyards and tasting rooms, many along Main Road/Route 25; although the majority are in nearby Peconic or on the way, Southold hamlet boasts One Woman’s Wine & Vineyards near Route 48 on the northern coast. The organic fruit of Bhavana Blueberries is not far. Back in the center, there’s comfort food to be had at Erik’s Breakfast & Lunch, O’Malley’s, and Founders Tavern. For seafood, the choicest spots are A Lure and Southold Fish Market.