Greenport is a cozy little town with great little shops,...
Greenport is a cozy little town with great little shops, excellent restaurants and plenty of accommodations, from B&B's to "fancy" hotels with all the amenities. Most everything is within walking distance. I've stayed at The Bartlet House (now called Tapestry), a beautiful, 10 room B&B, and the Townsend Manor, a Hotel/marina with a main building and two or three "cottages" with about 4 rooms in each. Townsend could use some updating, but its got a ton of character and the rooms are comfy and clean. The Coronet Diner was falling into disarray, but was recently sold, and the new owners have done a fabulous job of updating while keeping the "retro" feel of a 1950's diner. And the food and service is excellent! It's now called "Crazy Beans," and its open for breakfast and lunch.
You can rent bikes in town and explore the town or hop on the ferry for a short ride to Shelter Island. Or have a cocktail at the outdoor bar at Claudio's. The various wineries in the area offer wine tastings almost year round, and there are plenty of farmstands and markets, as well as pumpkin picking in the Fall. All in all, plenty to do year-round.
I live on Long Island only about an hour or so West of Greenport and when I'm there, I really feel like I'm "away." Greenport exudes a feeling of nostalgia - between the beautiful old houses in the area, the shops and the community atmosphere, you feel like you stepped back to a simpler time - yet it doesnt lack for any of life's modern conveniences. A truly great place to experience!