Connected by a granite causeway to the mainland at Pleasant Point Reservation, Eastport has wonderful views of the nearby islands, and you can sometimes spot whales from the waterfront because the harbor is so deep. Known for its diverse architecture, the island city was one of the nation's busiest seaports in the early 1800s. On the weekend after Labor Day the Eastport Pirate Festival brings folks out in pirate attire for a ship race, parade, fireworks, cutlass "battles" by reenactors, and other events, including a children's breakfast and schooner ride with pirates.
Get downtown early to secure a viewing spot for Maine's largest July 4th parade. On the weekend of the second Sunday in August, locals celebrate Sipayik Indian Days at the Pleasant Point Reservation. This festival of Passamaquoddy culture includes canoe races, dancing, drumming, children's games, fireworks, and traditional dancing.