Halloween is a great excuse to revisit old stories, and Casco Bay has plenty of them. Portland has been a working harbor for centuries, and the waters around it have collected their share of legends along the way. One of the best known, which we first shared on this blog in 2018, is about a War of 1812 privateer that left Portland Harbor in January 1815 and never came back. According to generations of fishermen and islanders… she has been seen trying.
Meet the Dash.
A ship built for speed
The schooner Dash was built in 1813 at Porter’s Landing in Freeport. As the history of that once-busy shipbuilding village records, she was the work of shipbuilder James Brewer, built for brothers Seward and Samuel Porter. Above all, she was designed to be fast. With British warships blockading the New England coast, a merchant vessel’s best defense was simply not getting caught.
Her early voyages were trading runs south, carrying New England goods out and bringing coffee back. When a British man-of-war gave chase, she lived up to her name and left it behind. After a few successful runs, the Porters had her refitted with heavier guns and sent her out as a privateer: a privately owned ship legally authorized to capture enemy vessels and keep the proceeds. Piracy with paperwork, essentially.
She was very, very good at it. Genealogists at WikiTree, who have pieced together the ship’s history and the families of her crew, credit the Dash with fifteen prizes across seven voyages. That made her one of the most successful privateers ever to sail out of Maine, and by most accounts she did it without losing a single man.
The last race
In January 1815, the Dash readied for another voyage under Captain John Porter, brother of the owners. His brothers Ebenezer and Jeremiah were among a crew of roughly sixty. Nobody aboard knew the war was already over. The Treaty of Ghent had been signed on Christmas Eve, 1814, but news of the peace was still making its weeks-long way across the Atlantic by sail.
She sailed out of Portland Harbor alongside the Champlain, a privateer out of Portsmouth, and the two crews agreed to a friendly race. True to form, the Dash pulled ahead. Then a snowstorm swept in, the Champlain lost sight of her, and that was the last anyone saw of the Dash.
As Big Think recounts in its telling of the story, she is believed to have been wrecked on the shoals of Georges Bank. No wreckage was ever found, and none of her crew came home.
She keeps coming back
Within months, the tales began circulating. Fishermen and islanders reported a schooner under full sail gliding out of the fog toward Freeport: the Dash, heading for home. The New England Legends podcast, which devoted an episode to the ship, traces sightings off Freeport and among the islands of the bay. The most famous ones place her in Harpswell Sound, sailing hard for port and vanishing before she ever arrives. Local tradition holds that she appears when someone connected to her lost crew is nearing a final voyage of their own.
The legend was durable enough that John Greenleaf Whittier turned it into a poem, “The Dead Ship of Harpswell,” published in The Atlantic in 1866. Writer Marlene Pardo Pellicer has explored how Whittier’s poem helped carry the story well beyond Casco Bay.
Sightings have been reported well into the twentieth century. That is either compelling evidence of the supernatural or compelling evidence that Casco Bay fog can make a lobster buoy look like anything you want it to. We’ll let you decide.
Keep a weather eye out
The next time you’re riding the ferry back from the islands at dusk, take a long look into the fog. If you spot a schooner with every sail set and no wake behind her, you may have just seen the fastest ship ever to leave Portland Harbor, still racing two hundred years on.
From all of us at Casco Bay Lines: Happy Halloween. Travel safe, dress warm, and we’ll see you on the water!