South ferry

 
  Pipes Cove Oysters Friskafella
 
  Shinn Estate Vineyards

Did You Know?
During Prohibition, illegal spirits made their way (by the shipload) from the southern islands through Greenport on their way to New York City. Greenport was always more than just a whaling town: More than 550 ships were built and launched here from the 19th to the mid-20th century. During World War I, the Greenport Basin & Construction Company constructed ships for the Russian and US navies; in World War II, the same shipyard built tugboats, mine sweepers and landing crafts. Today Greenport is bustling with friendly local merchants, restaurants and a lucrative oyster industry.

Established in 1678, Mattituck is home to award-winning wineries, breathtaking views of the bay and sound, and the annual Strawberry Festival: Every year in late June, at the peak of the strawberry harvest, thousands of berry lovers descend upon Mattituck for the annual affair. Visitors can feast on strawberry shortcake and chocolate-covered strawberries and watch as the town crowns the Strawberry Queen. There are roller-coasters, live music and, of course, strawberry daiquiris.

Modes of Transport
If you are coming from the South Fork, you are going to need to come by sea. Take the south ferry from North Haven to Shelter Island, then follow Route 114 as it meanders through the lush landscape of Shelter Island all the way to the north ferry, which will take you right to Greenport. Ferries leave every 10 to 20 minutes. 749-0139; northferry.com

On the Water
You cannot visit Greenport without stopping by Claudio’s. Opened in 1870 by a Portuguese whaler named Manuel Claudio, it has been the North Fork’s premier dining (and drinking) destination for more than 140 years, which makes it the oldest same-family-run restaurant in the United States. Stop by for a flight of North Fork wine paired with local oysters and Claudio’s specialty baked clams: chopped Peconic Bay bivalves mixed with Claudio’s own special blend of herbs and spices. As you settle in at the Victorian Bar (rescued by Claudio himself from a hotel being torn down in New York City’s Bowery in 1885) and gaze at the mirrored saloon door, you can feel the history of Greenport all around you. 111 Main St., Greenport, 477-0627