Eastport Pirate Festival in Eastport
Eastport Pirate Festival takes over downtown Water Street the weekend after Labor Day, turning Maine's easternmost city into three days of costumes, contests, and harbor-side mischief. A pirate comedy fundraiser each July helps build anticipation ahead of the main September weekend, tying the two events together across the summer.
On Water Street, the harbor is right there beside you and the whole downtown feels like it has agreed to play along: striped shirts, weathered boots, laughter rolling toward the water, and a main stage throwing music out into the sea breeze.