The well-protected harbor at Greenport has drawn vessels for centuries. Once a whaling and shipbuilding port, it later became a menhaden fishery and oyster center and eventually offered a haven for tourists. Today, visitors come by land and sea with loyal boaters flocking to this destination during the summer months.
Claudio’s, a waterfront landmark, is an eatery established in 1854 by ship worker Manuel Claudio. A magnet for boaters and a bootlegging stop during Prohibition, the restaurant is a popular East End destination. Preston’s Chandlery, a mariner’s browsing treat that dates back to the late 1800s, is another village institution.
For a deep dive into Greenport’s seafaring past, visit the East End Seaport Maritime Museum at the ferry dock. The museum scoots visitors out to the iconic Long Beach Bar “Bug” Light and stages the Greenport Maritime Festival in September. In Mitchell Park, an antique 36-horse carousel makes daily rounds, and the Railroad Museum of Long Island tracks Greenport’s history as the eastern terminus of the Long Island Rail Road.
You can easily branch out from here to Gunkhole in Peconic Bay estuary. Visit a Long Island winery, tee off at a golf course, or take a short jaunt to Shelter Island on the ferry. Dering Harbor and Coecles Harbor have facilities at Shelter Island for transient boaters.
