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Greenport village, originally named Winter Harbor, has a long maritime history. Surrounded by natural charm and beauty, Greenport Village has been the destination town of the Northfork for artists and vacationers ever since the Long Island Railroad brought service to Greenport in the second half of the 1800's. If you are visiting Greenport, check out the many shops, art galleries on Front and Main streets for local arts and crafts. They have some great things and it is even fun if you are just window shopping. For more information: http://www.greenportvillage.com/
The highest rated Bed and Breakfasts of Long Island are located right in Greenport Village, as are a few hotels. Fine dining, featured in reviews from the NY Times and Conde Nast, is concentrated on Main and Front Streets; however great wine bars and restaurants can be found tucked away in marinas and down sidestreets throughout the Northfork. For casual dining local pizza bars and markets with takeout food can be found throughout the village.
There are over 40 vineyards within a 10 minute plus ride. There are companies you can hire to drive you around if you are worried about drinking and driving. There is even a microbrewery in the heart of the town, and it is a great time. When you stay at a B&B, be sure to ask your hosts for help. They know the area and can help you have the perfect vacation. Use them as resources.
Visitors with children will enjoy the Carousel in Mitchell Park at the Harbor in Greenport. People can also ice skate now in the Winter at Mitchell Park, as well. Teens can enjoy the skate park on More's Lane which includes half-pipe, street course and mini-ramps...safety gear required. That is also the location of many carnivals during the Summer
Cyclists and hikers have many options to explore as well: a half dozen nature preserves ( http://southoldtown.northfork.net/ ) and some with beach access as well as bike trips that take you by a half dozen vineyards. Check out http://www.mapmyride.com/us/southold-... .
There are a few tour boats that take cruises around the beautiful Greenport Harbor and Gardiner's Bay, including a "Green" boat named The Glory that is run on solar charged batteries. If fishing is your passion, then half day trips leave from the dock behind the old train station, now the Maritime Museum. Or take a 15 minute ferry ride to Shelter Island by foot, bike, or car to explore another historic neighborhood.
In the vicinity, are wonderful golf courses, museums, lighthouses and so much more.
A major attraction is Long island Wine Country. They are located on Rt 25, 4 minutes from Greenport Village. You can also check the website liwines.com put out by the Long Island WIne Council, for complete information, including hours and tour info.
There are some superior winery tour companies. Again ask your B&B/hotel host for help with booking .
You will not believe how much there is to do out here, so plan at least 3 days, as any less will not come close to scratching the surface.
Once you visit, it will become a place to return to again and again.