Summer (July and August) is prime time: whale-watching tours run, the weather is as warm as it gets on the Bay of Fundy, and the town has the most life. The Fourth of July celebration is a genuine small-town spectacle — Eastport throws a big parade and fireworks for its modest population. The Pirate Festival in mid-September draws a crowd and adds colour to the waterfront. Shoulder season (June and October) brings fewer visitors, lower prices, and the full dramatic swing of the tides without summer competition.
Winter is very quiet. Many businesses close, and the town retreats into itself. But if you want solitude, dramatic tidal ice, and the kind of light that photographers travel far to find, January and February on the Passamaquoddy Bay have a severe beauty. Pack for cold and wet in any season — this is Maine's coast, and the Bay of Fundy keeps things cool even in July.