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Destinations To Die For: Greenport, New York

Whaling and Wine | June


Preston's marine-supply store in Greenport's Harbor Wharf opened in 1880.

I first became smitten with Greenport, New York, after my friend Caroline was married there a few years ago. The wedding took place in a small, white chapel in this historic fishing village, and the locals driving by stopped and honked their horns when they saw the beautiful bride. The reception was held nearby, under a big tent on the grounds of one of the many scenic vineyards on the North Fork of Long Island. I've been back to Greenport many times since that weekend, and each time I find myself falling in love with this picturesque little village over and over again.

Located on the Peconic Bay side of the North Fork, Greenport is ten miles from Orient Point, the most easterly tip of the peninsula, and only a mile and a half from Long Island Sound. The town became a major whaling port in the early 1800's and was later home to the Basin and Construction Company, which built vessels for the Russian and U.S. navies in the Second World War.

Although Greenport has become a popular summer escape for weary Manhattanites, its nautical history has not been lost. The maritime museum and marine stores are just as popular as the waterside restaurants, antique shops, and artists' galleries. And there seem to be as many marinas welcoming out-of-town guests as there are B&Bs.


Greenport's 9/11 memorial is an osprey atop a beam from the World Trade Center wreckage.

The importance of Greenport's maritime history is well known, but it was the arrival of the Long Island Railroad that connected this salty village to the outside world. According to the town's Railroad Museum, the three excursion trains that left Brooklyn on July 27, 1844 were the first to test the newly completed line that ended in Greenport, 100 miles east. They were scheduled to arrive five hours later, so everyone—even the project engineer—was amazed when they arrived in just three and a half hours. (Today the trip still takes three hours.)

The railroad may still be the quickest way to get out to Greenport, but it is certainly not the most scenic. Cruise around Orient Point and into Great Peconic Bay, where you'll find other charming waterfront towns like Jamesport and Sag Harbor. Whatever your itinerary is, be sure it includes Shelter Island. Home to the 2,000-acre Mashomack Preserve, the island is a popular spot for hiking and bird watching. Follow the ferry from Greenport, and it will lead you into Dering Harbor, where you can rent bicycles and explore the only real town on the island. Or head around to the southeast side for a delicious meal at the Ram's Head Inn in Coeckles Harbor. After perusing the seasonal menu and long list of local wines, you may want to avail yourself of a complimentary mooring and enjoy a night in the quiet harbor before heading back to Greeport in the morning.

Destinations To Die For

January: Plymouth Harbor, Dominica
February: The Spanish Virgin Islands
March: Mazatlan, Mexico
April: Man-O-War Cay, Bahamas
May: Southport, North Carolina
June: Greenport, New York
July: New York, New York
August: Penobscot Bay, Maine
September: Block Island, Rhode Island
October: Panama City, Florida
November: Key West, Florida
December: Staniel Cay, Bahamas

This article originally appeared in the December 2007 issue of Power & Motoryacht magazine.