Although Kennebunkport is a popular summertime stop on the East Coast, and a truly magical small town in the fall, it still has its own charm in the winter. The photogenic city hosts many wintertime shopping and dining events, especially in February, where the city celebrates Valentine's Day all month long. For a sweet winter couples retreat, cozy up in a B&B for the weekend. Take a horsedrawn carriage ride through Dock Square to see the many business participating in "Paint the Town Red," which involves hanging red lights and decor and offering special “red plate” meals and “red tag” savings. Enjoy chocolate and wine tastings, a Valentine's dance, a winter carnival and skating party and more.