Sag Harbor

On the South Fork's north coast, Sag Harbor has a strong maritime flavor that largely stems from its history as a whaling port. The first white settlers arrived in the late 1600s, learned a thing or two about whaling from the resident Native Americans, and started sending out whaleboats in the mid-1700s. By the time the industry hit its peak in the mid-1800s, Sag Harbor had become one of the world's busiest ports.

Sag Harbor's centuries-old Main Street, lined with boutiques, galleries, and restaurants, leads to the wharf where tall ships from around the world would arrive. Today impressive sailboats and powerboats line the marina and bay. Thanks to careful preservation, much of Sag Harbor's 18th- and 19th-century architecture remains intact, including Greek-revival houses once owned by whaling captains. Also abundant are early-colonists' homes as well as Victorian houses built for wealthy industrialists.