Greenport on Long Island’s north fork should be a port of call for every cruiser. Established in 1682, Greenport lies on the south side of the north fork opposite Shelter Island. Forbes Magazine called it “one of the prettiest towns in America” Its nautical history goes back centuries in whaling, fishing and boat building. Because of its location, rum-running was a lucrative business during prohibition. During that time it was widely known that Claudia’s served booze to its patrons. Greenport is still active in fishing and oystering.
When visiting Greenport from the Long Island Sound you need to navigate through Plum Gut, also known as The Race between Orient Point and Plum Island. If the tide is against you it will get a little bumpy but will not be a problem for a normal powered boat. If you are a sailboat going against the tide with an opposing wind, make sure you can power through it. I have seen nice rips and waves here several times. When pushing through Plum Gut watch your charts and keep the Orient Point Lighthouse on your starboard. Do not pass between the lighthouse and land here. While here always give way to the ferry boats.
Once through the Race, keep the Orient Point Beach State Park to your starboard and look for the Long Beach Lighthouse on your starboard as well. Continue heading west with Shelter Island at your port bow eventually and go to no-wake speed once you reach the jetty at Greenport Harbor.
For docking, we liked Mitchell Park Marina (www.greenportvillage.com) because it ties you up adjacent to town where you can walk to everything in 10 minutes. Another docking option is at Safe Harbor making a hard to starboard turn up the channel. We have docked free here as part of the reciprocal policy when you are a member of other Safe Harbor Marinas. (www.byy.com/marinas/greenport-yacht-yard-greenport-ny) Safe Harbor has fuel and is a 25-minute walk to town.
Greenport is one of the more nautical feeling villages on Long Island. It has commercial piers with fishing boats. The large docks near Mitchell Park Marina sometimes have large yachts or historic boats to admire.
To taste the region I put on my “Locavore” hat and made a beeline to The Little Creek Oyster Farm and Market (https://littlecreekoysters.com/). Here you can enjoy the oysters that came out of nearby waters along with a beer brewed just down the block. On weekends you may have to be patient and wait for one of the several outdoor tables.
After your very fresh snack explore the village. Continue on the waterfront park and you will get to the 100-year-old Jesse Owen Carousel where you may be able to get a free ride if you win the ring. Front Street adjacent to the waterfront park connects with Main Road forming the core of Greenport’s businesses. Here you will find boutiques, bars, ice cream, a cheese shop, knick-knack shops, a dozen restaurants, a brewery and their signature nautical store called Preston’s Channery. Our restaurant picks were the Green Kitchen, Lucharitas and the outdoor dining at Port Waterfront Bar and Grill. We found the famous Claudio’s hit or miss depending on the time we went in the past. We always stop in at old fashioned, Burton’s Bookstore for local information, used books as well as the latest novels.
If you like older homes than stroll the Greenport Village Historic District that was added to the National Register of Historic Places in 1986. This district contains 254 structures from 1750 to the 1930’s. You can walk around the entire area in about an hour.
On the west end of town visit the East End Seaport Maritime Museum housed in the former railroad station (www.eastendseaport.org). There you will find exhibits on the village’s shipbuilding history, along with information on the region's wildlife and a working blacksmith at the Village Blacksmith Shop. The museum hosts a street long maritime festival in September.
Greenport is a good base for land activities. If you have bicycles you can visit my favorite north fork wineries just 40 minutes away on a flat road. These include Bedell, Lenz and Sparkling Pointe. If bikes are not on board you can take a short taxi ride to Bedell and walk to the other vineyards near them. The Kontokosta Winery is a 30 minute walk north of Greenport. Many vineyards on weekends have entertainment. Some allow you to bring a picnic lunch so call ahead or go on their web site.
For evening entertainment see what is playing at the restored art deco Greenport Theater. Some of the restaurants and bars have music on weekends. For information on Greenport click https://www.greenportvillage.com/about-greenport/
While cruising this area consider a visit to Riverhead. You can access my L.I. Boating World story by clicking www.liboatingworld.com and in the search box type “Riverhead Tab Hauser” For quiet time on the hook nearby, circle Shelter Island to the east and stay a couple of nights in the very protected Coecles Bay.
Tab Hauser is a U.S. Coast Guard licensed captain and a member of the Explorer’s Club. He has been boating on Long Island since 2006. Offseason he is a travel writer and event photographer seen at www.tabhauserphoto.com and www.tabhauser.com