Smithtown, NY real estate market

Smithtown takes its name from Richard Smith, and the story locals still tell involves a bull. Legend says a Nissequogue chief promised Smith all the land he could ride around in one day on a bull's back, and Smith picked the summer solstice of 1665 to get the most daylight out of the deal. A statue of that bull, called Whisper, stands today at the fork of Jericho Turnpike and St. Johnland Road. The real paperwork is less colorful. Lion Gardiner helped return the kidnapped daughter of Grand Sachem Wyandanch, Wyandanch granted Gardiner land in thanks, and Gardiner sold it to Smith in 1663. Governor Richard Nicolls made it official with a patent in 1665, which is why that year marks the town's founding. The road along the Huntington border, Bread and Cheese Hollow Road, supposedly follows part of Smith's original route, and that same border was the site of Fort Salonga, where a Revolutionary War battle was fought in 1781.

The town sits on the North Shore of Suffolk County, with Long Island Sound to the north, Islip to the south, Brookhaven to the east, and Huntington to the west. It covers 111.5 square miles total, but more than half of that, 57.7 square miles, is water. Town hall has stood on Main Street in the hamlet of Smithtown since 1912, and it was renamed in 2015 for former Supervisor Patrick Vecchio, who held the job for forty years. That same year the town marked its 350th anniversary with a new statue of Richard Smith at Main Street and Route 111, which gives you a sense of where the civic center of gravity sits.

Smithtown proper is one hamlet among several, including Kings Park, St. James, Nesconset, and part of Commack, which it shares with the Town of Huntington.