A shout-out belongs to Chris Mackowski, who recognized this story’s drama much sooner than I did, and has been asking that I write this series for over a year now—I should have followed his advice much earlier. I grew up in southern Maine, only about a 10-minute drive from Portland, and even with my interest in the Civil War that started at an early age, I did not know about the battle of Portland Harbor, which occurred on June 27, 1863. Perhaps ironically, it was not until I came to Virginia for college, about 600 miles from home, that I learned about the battle that occurred just a hop, skip, and a jump away from my house.
This post, part one of a series, serves as a prologue.
The story of the Battle of Portland Harbor begins on May 6, 1863 and close to 4,000 miles from where it ends. Off the coast of Brazil, near the Cape of Saint Roch, the C.S.S. Florida captured the supply ship Clarence, bound for Baltimore. The Clarence was a brig, weighing 253 tons, with an overall length of 114 feet.
Aboard the Florida, Second Lieutenant Charles Read got an idea. Read, just six days shy of his 23rd birthday, graduated last from the Naval Academy at Annapolis in 1860 but then, like so many other southerners, resigned his commission upon secession. As the second-in-command on the Florida, Read was looking to make his own impression in the ongoing war. On the same day as the Clarence’s capture, Read wrote to his superior, Commander John Maffitt, also aboard the Florida, “Sir: I propose to take the brig which we have just captured, and, with a crew of twenty men, to proceed to Hampton Roads and cut out a gunboat or steamer of the enemy.”
Read’s suggestion of swooping into Hampton Roads, even to capture just one ship, was daring. Since the creation of the blockade in 1861 Hampton Roads had served as the “main base” for the North Atlantic Blockading Squadron; there were ships and the heavy guns of its forts that could reduce Read’s attack into splinters of wood and blood.
But Read saw a way to avoid detection, continuing in his proposal to Maffitt, “As I would be in possession of the brig’s papers, as the crew would not be large enough to excite suspicion, there can be no doubt of my passing Fortress Monroe successfully.” Armed with the Clarence’s pass as a Federal supply ship in other words, Read planned to attack Hampton Roads as a wolf in sheep’s clothing.
Maffitt was impressed with his subordinate’s plan. The same day he received Read’s proposal he responded, “The conclusion come to is that you may meet with success by centering your views upon Hampton Roads…. The proposition evinces on your part patriotic devotion to the cause of your country, and this is certainly the time when all our best exertions should be made to harm the common enemy and confuse them with attacks from all unexpected quarters. I agree to your request… Act for the best, and God speed you.”
Transferring to the Clarence, Read took twenty men from the Florida’s crew, along with one 12-pounder howitzer. To supplement his small arsenal, Read’s new crew constructed a number of wooden “Quaker guns” that, at a distance, would look real and maybe dissuade any notions of combat. With his orders, Read set sail and moved north. In the Windward Islands Read “chased several vessels, but failed to overhaul them on account of the inferior sailing qualities of the Clarence.”
The Clarence’s fortunes changed, though, on June 6, off the coast of North Carolina. Seeing the Whistling Wind, a ship carrying coal, Read used a bit of deception. Hiding the howitzer and bringing in the fake guns, Read ran up an American flag, upside down in a sign of distress. When the Whistling Wind heaved to and pulled up alongside the Clarence, Read’s men quickly jumped aboard, captured the unarmed crew, and transferred the Federals ship’s supplies back to the Clarence. Then, as night fell, the Whistling Wind was set on fire.
The following day Read captured a second ship, the Alfred H. Partridge. Reading the dispatches from both the Whistling Wind and Alfred H. Partridge Read came to the conclusion that, “I derived such information as convinced me that it was impossible to carry out the instructions of Commander Maffitt. No vessels were allowed to go into Hampton Roads unless they had supplies for the U.S. Government, and they were closely watched.” But Read also refused to call off his expedition, changing his objective “to cruise along the coast and try to intercept a transport for Fortress Monroe and with her to endeavor to carry out the orders… and in the meantime to do all the possible injury to the enemy’s commerce.”
With his new plan, Read sailed further north, continuing his spree of capturing Federal ships. On June 9 the Clarence captured and then destroyed the Mary Alvina. The Confederates continued sailing north, and on June 12, Read captured the Tacony, a bark weighing 296 tons. Read recognized the Tacony as faster than the Clarence, so once the 23-year old had transferred his crew, provisions, howitzer, and Quaker guns, he burned the ship that had been his home for the past month and six days.
Now in the Tacony, Read continued his already impressively destructive voyage. In the fast Tacony, Read captured another fifteen vessels, and, on June 24, 1863, captured the sixteenth, the Archer. Since leaving the Florida on May 6, Read had captured and destroyed twenty vessels, some carrying coal for the blockade squadrons, others arms and provisions for the variety of Federal field armies. His adventure and copious amounts of captures now brought the daring lieutenant off the coast of Maine.
Read’s exploits had not gone unnoticed, however. Word of his captures got out and Read later wrote, “As there were now a number of the enemy’s gunboats in search of the Tacony, and our howitzer ammunition all expended, I concluded to destroy the Tacony, and with the schooner Archer to proceed along the coast with the view of burning the shipping in some exposed harbor….”
The exposed harbor that Read chose was Portland, Maine’s largest commercial city. On June 26 Read picked up two fishermen, again hiding his cannon and menacing crew, and the civilians “who, taking us for a pleasure party, willingly consented to pilot us into Portland.” The Archer sailed past Portland Head Light, still one of Maine’s most-popular tourist attractions, and glided into Portland Harbor.
Making conversation the fishermen, still unaware of Read’s true intention, let the Confederate know that, “the revenue cutter Caleb Cushing was in the harbor of Portland….” Read immediately had his next target. Come nightfall, under the cover of darkness, he would attack the Caleb Cushing. Though Charles Read did not know it, it was that decision that would start the Battle of Portland Harbor.
 Paul H. Silverstone, Civil War Navies: 1855-1883 (New York: Routledge, 2006), 162.
 Official Records of the Union and Confederate Navies in the War of the Rebellion, Ser. 1, Vol. 2, 644. (hereafter cited as OR Navies). This is the naval addition to the more-popular The Official Records of the Union and Confederate Records– the famous “ORs”.
 Ivan Musicant, Divided Waters: The Naval History of the Civil War (New York: HarperCollins, 1995), 136.
 OR Navies, 644.
 Ibid, 645.
 Ibid, 655.
 David W. Shaw, Sea Wolf of the Confederacy: The Daring Civil War Raids of of Naval Lt. Charles W. Read (New York: Free Press, 2005), 108-110.
 OR Navies, 655-656.
 Silverstone, 162; OR Navies, 656.
 OR Navies, 656.