Casco Bay's 222 square miles of island-studded water have carried ferry traffic since 1845, when the first scheduled mail boats began threading between Portland and the Calendar Islands—so named because early settlers believed the archipelago held 365 landmasses, one for each day of the year.
The actual count hovers near 136 depending on tide and definition, but the romance of the name persists. By the 1870s, recreational steamship excursions had become a mainstay of Portland's summer economy, carrying city dwellers past granite ledges and spruce-crowned islets to seaside hotels on Peaks and Great Diamond islands. The working waterfront at Commercial Street, where Casco Bay Lines maintains its terminal today, has operated continuously as a transit hub for over a century and a half.
Evening sailings trace routes that predate modern navigation aids. Portland Head Light, commissioned by George Washington in 1791, still flashes its four-second sequence from the rocky promontory at Cape Elizabeth. Spring Point Ledge Light, built in 1897 on a caisson foundation, marks the entrance to Portland Harbor with a cast-iron tower that survived the 1938 hurricane and the February gales of 1952. Ram Island Ledge Light, automated in 1959, rises from a granite pier a mile offshore, its conical profile unchanged since 1905. These sentinels frame the bay's eastern and southern approaches, their synchronized rhythms readable from any vessel transiting the shipping lanes.
The sunset cruise route typically departs from the Casco Bay Lines terminal at 56 Commercial Street, following the deepwater channel past the container port and Fish Point, then arcing southeast toward Portland Head. Passengers aboard the diesel-powered Bay Mist or the seasonal schooner fleet pass within a quarter-mile of the lighthouse's 80-foot tower, close enough to distinguish the keeper's quarters from the fog signal building. The return leg cuts northwest through Hussey Sound, skirting the cliffs of House Island—a Civil War fortification abandoned in 1946—before rounding back to the terminal as harbor lights kindle along the Old Port wharves. Departure times shift with the sun's declination, but the 90-minute circuit remains constant, timed to catch the final hour of daylight over open water.
1 hr 45 min
