Windjammer Days, held in late June, is Boothbay Harbor's biggest annual event. A fleet of traditional schooners and tall ships sails into the harbor and anchors for several days, giving the town an atmosphere straight out of the 19th century. The festival runs for about a week, with a parade of sail, live music on the waterfront, street food, and an arts fair alongside the usual summer commerce.
The event draws visitors from across New England and regularly fills every room in town — book accommodation well in advance if you plan to be there for the festival. Even if you're visiting outside the festival dates, the harbor in early summer has a good concentration of working boats and charter vessels that keep things interesting.