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The Battle of Portland Harbor was a naval battle of the American Civil War, fought June 27, 1863, at Portland, Maine.

The Confederate raider Tacony, commanded by Lt. Reed (the after action report states his name as C.W Reed, but it's debated if that is his true name), captured the fishing schooner Archer off Portland, Maine. Realizing the Union navy was pursuing his ship, Reed and his men burned the Tacony, then slipped into Portland harbor about two days later aboard the Archer. Once in the harbor they captured the revenue cutter Caleb Cushing (named after the Massachusetts Congressman, Caleb Cushing) early on June 27.

With both the Archer and the Caleb Cushing, Reed and his planned to slip out past the harbor forts before anyone knew what had happened, then return to set fire to the commercial shipping. However, word had gotten out of the Confederate presence in Portland Harbor. Troops from the Seventeenth Infantry, stationed at Fort Preble in South Portland, Maine had been sent to destroy the Confederates and their captured ships. 28 men armed as infantry were sent out, along with 10 men to man a 6-pounder field piece and a 12-pounder howitzer. The troops boarded the "Forest City", a civilian cruise ship. The startled civilians onboard were supplied with muskets for their defense.

Within 2 miles of the "Caleb Cushing", the "Caleb Cushing" opened up with its 32- pounder field piece. The startled captain of the "Forest City" refused to continue his pursuit of the "Caleb Cushing". So the soldiers had to wait for the "Chesapeake". Before the "Chesapeake" could arrive, the "Caleb Cushing" was already in flames, and the Confederates onboard were escaping on the lifeboats. The "Chesapeake" headed after the lifeboats and succeed in capturing the captain C.W. Reed, and all 24 the crew of the "Tacony". Quickly afterwards, the "Archer" was captured. Upon search of the prisoners, $92,500 of bonds were discovered, all payable thirty days after "the ratification of a treaty of peace between the United States and the Confederate States of America" The prisoners' lives were at great risk, so a large group of soldiers were ordered to defend them. So much time was spent with the protection of the prisoners, that the Major of the Seventeenth Infantry sent a telegram to the Secretary of War, Edwin M. Stanton, requesting more troops to guard the prisoners. Soon the prisoners quietly left Fort Preble under the cover of darkness.