Southold History & Culture
Though miles of Long Island Sound divide Southold and Connecticut, the former was considered part of the latter for the first few decades after its 17th-century founding. 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 to have distinct areas to immerse yourself in hamlet life or get away from it all. Like any worthwhile main street, Main Street is a hub for activity. However, turn off Main — 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.