Take a close look at the chandelier in Portland’s First Parish Church, just up the street from City Hall: there’s a cannonball hanging from the end of it. Poke around under the pews and you’ll find more ordnance plucked from the walls of the Old Jerusalem Church, a wooden structure that stood on the site during the American Revolution, when the Royal Navy all but wiped Maine’s largest city from the map.

Portland, of all of New England’s rebellious towns, wound up being the one the British burned to the ground. Portsmouth, Salem, and York still have much of their late 17th and 18th century architectural heritage; in Portland, what little survived the 1775 naval bombardment was destroyed in the great fire of 1866.

So, why Portland?

On the face of it, anywhere in Maine seemed a poor target. Ever since Massachusetts had annexed Maine in the 1650s, residents of this coast had looked to the crown to protect them from the excesses of their overlords in Boston. The Anglican church — the Church of England — was stronger here, seen as a counterbalance to the official Puritan church of the Bay Colony.

But Britain’s response to the Boston Tea Party devastated Maine’s fragile economy. In 1774, the British closed the port of Boston to all American vessels, save those carrying food and firewood into the city, leaving Mainers without adequate provisions. The military governor in Boston assumed control of town meetings and local judicial appointments across New England. Many residents of Maine felt betrayed by the crown. Not a few descended into open rebellion.

Angry militamen from frontier towns like Brunswick and Gorham terrorized British sympathizers. The Brunswick militia, led by tavern keeper Samuel Thompson, broke into the Lincoln Country Courthouse to harass and humiliate the judges working inside. But Thompson had bigger plans: to surprise and capture a Royal Navy warship.

In April 1775, an opportunity presented itself. HMS CANCEAUX, a 180-ton, 8-gun converted merchantman, was paying a visit to Portland, then known as Falmouth, to protect a loyalist merchant ship. CANCEAUX’s commanding officer, 41-year old Lt. Henry Mowat, had spent the previous 11 years surveying the waters of Maine and Eastern Canada, but he’d recently been ordered to cut short his survey and to help the Navy enforce the King’s authority. Though Mowat was preparing to proceed to Halifax to repair CANCEAUX’s damaged keel, Vice Admiral Samuel Graves had ordered him to Portland instead, in the “hope her presence will be some check to the common disturbers” there.

The situation was tense. Three days after dropping anchor, a group of small boats approached CANCEAUX in a menacing fashion, refusing to respond to Mowat’s hails. They retreated only after Mowat’s men fired a splay of grapeshot in their direction, according to the CANCEAUX’s logs, which have recently been published as Voyage of the CANCEAUX (Heritage Press, 2003). Sleet, snow and drizzling rain made life uncomfortable for the 45 men who comprised her crew.

Meanwhile, Thompson’s men were fitting out a pair of sloops in Georgetown, intending to ambush the warship. They were forced to abandon this plan, however, after word if it got to Portland, whose town fathers could not be counted to keep such a secret. Thompson would not give up so easily. In the middle of the night of May 8, Thompson and 60 of his men landed on the backside of Portland neck, where they waited in the woods for their chance to make a move.

It came the very next morning, when Mowat decided to take a stroll ashore with the local Anglican minister. On the outskirts of town he was captured by Thompson’s men, who wore spruce twigs in their hats and carried “a spruce pole with a green top on it” as their battle flag. CANCEAUX’s first officer responded by discharging two if his cannon towards the town. “Although there were no shot in them,” resident Jebediah Preble recalled, “it frightened the women and children to such a degree that some crawled under wharves, some ran down cellar, and some out of town.” In reaction, some 600 miltiamen poured into the town to protect Thompson and ransack loyalist homes.

The town fathers, fearing the town would be bombarded, came to the pub where Thompson was holding his prisoners and talked him into letting the officer go. Even so, the visiting militia continued to take pot shots at the CANCEAUX, and loudly threatened to set it on fire. Mowat demanded that Thompson be turned over to him, but instead the townspeople “treated Col. Thompson with civility, and his men were [fed] at the expense of persons in this town, as long as they pleased to tarry” there. After a few days of frustration, Mowat gave up and sailed for Boston.

Mowat would have his revenge, however. In October, following a series of deadly attacks on Royal Navy personnel, Admiral Gage ordered CANCEAUX to punish the rebellious ports of northern New England. Marblehead, Gloucester, Newburyport, Portsmouth, Saco, and Machias were all slated for destruction, but it was Portland that would pay the price.

On October 16, Mowat returned to Portland with the Canceaux and four support vessels, and, after a night’s warning, opened fire on the town. Witnesses said the bombardment lasted for nine hours “without many minutes cessation” triggering fires that burned three-quarters of the buildings in the city, including the entire downtown clustered around what is now India Street. The Old Jersusalem Church escaped the fire because it was located in what was then the fringe of town, but several cannonballs tore through its wooden walls. At several points, Mowat landed marines ashore to set fires in undamaged neighborhoods, leading to musket battles with local militia. The downtown never recovered from this blow, and in the aftermath the city center moved instead to what is today the Old Port.

The bombardment shocked public opinion in both America and England. “To burn a town thus in cold blood surpasses every idea of savage barbarity and brutality,” read one letter to the London Public Ledger. “If I, an Englishman unconnected with America…am thus agitated… what effects must it have produced in the breasts of those who saw their habitations smoking in ruins?”

The King’s Navy had shown itself be far more of a threat to life and property than Thompson’s rough backcountry militiamen. Britain had lost the hearts and minds of Maine’s people, who would stand firmly behind the revolution from then forward.

— Colin Woodard is the author of The Lobster Coast: Rebels, Rusticators, and the Struggle for a Forgotten Frontier. His new book, The Republic of Pirates, comes out in May. He maintains a website at colinwoodard.com.