History & Culture
Though miles of Long Island Sound divides the two points, Southold was considered part of Connecticut for the first few decades after its 17th-century founding. Actually, the story goes that residents of Southold quite preferred the Connecticutter life until the then-colonial government forced their hands. Perhaps this has contributed to the hamlet—and the North Fork at large—feeling decidedly more coastal New England than Empire State. While not massive, Southold is large enough that it has distinct areas to either immerse yourself in hamlet life or to get away from it all. Like any worthwhile main street, Main Street is a hub for activity. However, turn off Main Street—or head further north past Route 48—and you’ll find things are more open and tranquil. If you grow tired of Earth entirely, spend an evening stargazing and staring toward far-off galaxies at Custer Observatory, the oldest structure of its kind on Long Island.