Greenport, Long Island is a place I discovered two years ago when my sister moved there to open up her own store. It is a long drive from Rochester, NY, but always worth it. Greenport is a fishing town with a true New England feel. (Connecticut is right above it after all. This is a tiny town with many sights to see, shops to go to, and restaurants to eat at.
One surprise about the Eastern tip of Long Island is the many, many wineries that lead into Greenport once you drive through Riverhead. If I had to wager a guess, I would say there are 25 wineries. Most are very good!
Greenport has a lot of interesting history, and as a result, very cool old houses and buildings. Being a small village, they have been very successful in keeping out the chain hotels and restuarants. You will not find a McDonalds, Burger King, or Hilton here. Take advantage and have some of the local seafood pulled from the Atlantic Ocean and Long Island Sound.
If you have ever visit New York City, this is a nice diversion from the traffic and hordes of people that the city offers. Greenport has a lot of tourists, but everybody is pretty mellow compared to New York City.