Greenport is a charming seaside village located on the North Fork of Long Island, New York.
Settled in the early 1600s, the area has been a major hub for various nautical trades over the years, such as whaling, shipbuilding, and oystering.
During Prohibition, the port was a hotspot for smuggling alcohol, otherwise known as rum-running. You can even find a specific path between the buildings on Front Street called “Bootlegger’s Alley”.
The Greenport Village Historic District comprises 254 buildings that were built between 1750 to the 1930s. Among them are a jail, a schoolhouse, and an antique carousel.
In 2011, Forbes Magazine included Greenport in its list of “America’s Prettiest Towns”.