The coasting trade was—and is—reserved to American flag vessels, apparently, during the war years, Portland’s coasting fleet did a brisk business in carrying military supplies: cloth from Maine mills, foodstuffs and occasionally horses for the cavalry. On one occasion, however, the Civil War came right into Portland Harbor in 1863 when a daring band of Confederates under Lieutenant Charles Read anchored a captured fishing schooner off Fish Point, at the eastern end of Portland Neck. The plan to burn the gunboats Agawam and Pontoosuc, then fitting out at Franklin Wharf, and to capture the steam boat Chesapeake, but ultimately the Confederates settled for taking over the revenue schooner Caleb Cushing, which lay at anchor nearby. The capture went off without a hitch, but immediately nearly everything went wrong: the Cushing was aground; the wind dropped to a flat calm, and by the time they got the schooner free they had to take to the boats and tow her out. About eight in the morning, someone alerted the authorities and a wild chase down the harbor ensued. One of the hastily chartered vessels was the steamer Forest City, commanded by Society member Captain John Liscomb. Faced with capture, Read and men took to the boats and set the Cushing afire. Her ammunition blew up with a grand bang and the Confederates were handed over to the army at Fort Preble. The only casualty of the day occurred when a souvenir hunter picked up a loaded gun and accidentally shot and killed an onlooker.

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