Smugglers & Spies

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The clamor of a sleigh and the clomping of footsteps broke the silence of a brilliant moonlit night on the banks of the Penobscot River in Hampden in late December of 1814. Awakened by the noise, federal customs agent Charles Tebbets peered through his front window to see seven or eight men gathering outside his locked front door. One had a sword by his side and a pistol in his hand. There was a loud knock. “What’s wanted?” Tebbets asked through the closed door.

The man with the pistol replied he’d been robbed of some goods and he’d come to get them back. Tebbets insisted the goods were not in his house.

“You’re a lying rascal!” the stranger shouted, and he fired his gun into the air to underscore his point. Then he ordered his men to stave the door in.

Alarmed and badly outnumbered, Tebbets began to negotiate. He allowed two of the men inside. The strangers ransacked the house from cellar to attic, with Tebbets lighting the way and soothing the scared women and children of his family. The armed men did not find what they sought — a trunk of smuggled British goods seized by federal officials — and they left the badly shaken Tebbets family to return to their beds.

The War of 1812 looms large in Maine’s history because it led to statehood in 1820. Less well known is the fact that encounters like the one at the Tebbits’ household were common throughout the District of Maine, where smugglers and spies abounded. Some supported the American cause, while others undermined their own government by acquiescing or even colluding with the enemy. Many were simply opportunists looking to make a quick profit. Theirs is a complex story of survival, ideals clung to and sometimes abandoned, greed, selflessness, patriotism, and treason, all fueled by the same relentless combination of stresses from which a new state was eventually formed.

America’s “Second War of Independence” arose out of a complex combination of tensions that had been mounting for years. At war with France, the British Royal Navy had been interfering with American international trade, as well as harassing American merchant ships and impressing their sailors into its service against their will. At the same time, the United States was aggressively trying to expand into Indian tribal lands in northwest Canada, and the British supported the tribes whose lands were invaded. On June 18, 1812, under the rallying cry of “Free Trade and Sailors’ Rights!”, the United States declared war against Britain.

Most of the war was fought near or on the Great Lakes or out at sea. While only a secondary theater of the war, Maine was nonetheless profoundly affected. Communities that today, on the war’s bicentenary, are quiet and picturesque were then scenes of stress, discord, and treason. Residents of Kittery and Portland, for example, lived in constant fear of an attack by the Royal Navy. Eastport, Machias, Castine, Belfast, and Bangor were actually seized by enemy troops.

Without doubt, the British menace was real, but as the Tebbets family knew too well, the war also divided locals against each other and against their government. Indeed, Eastport’s citizens hated the American commander of the local fort so much they had him thrown into jail. And at the other end of the district, a debate about the war erupted into fistfights at a town meeting in Fryeburg. Waldoboro’s Germans largely opted out of the conflict, while officials in Portland debated whether the city’s nascent Irish populace should be considered enemy aliens or potential army recruits. The native tribes, meanwhile, receded deeper into the forests for fear of becoming victims of hysteria and racism.

Many communities remained cruelly divided long after the war ended. While some had done their patriotic chore and supported the war fully, others thought the war unjust and had bitterly opposed it. Especially in eastern Maine, there remained the question of how to respond to the locals who had openly and treasonously collaborated or traded with the enemy. The continued British occupation of Eastport from 1814 until 1818 only served to further embarrass and antagonize Mainers.


 Smuggling was a widespread phenomenon in Maine even before the war broke out. High federal tariffs made trafficking lucrative, and Maine’s long and porous border with Canada made it easy. Even the ostensibly respectable William King of Bath — who later became Maine’s first governor — was a smuggler, and his illicit trading methods no doubt added to his wealth, and thus his political influence. Ordinary fisherfolk were smugglers, too, as were many small farmers who drove cattle through the woods to Canada, knowing they would be paid in British gold.

While Eastport was one of the most notorious smuggling spots in the nation, customs officials found abandoned smuggled goods on beaches near Saco. Schooners ghosted alongside Widow Emerson’s wharf in York at midnight; and Portland retailers sometimes had difficulty explaining to the authorities how English goods arrived in their shops.

Violence was inevitable. Customs officials were threatened and sometimes beaten. A smuggler even killed a guard on remote Isle au Haut. Some officials found it easier to assist the smugglers than to confront them. York’s customs collector was jailed for colluding with smugglers, but escaped from the town’s ancient jail and fled to Nova Scotia.

With the advent of war, smugglers not only became busier, but by law their activities moved out of the realm of petty crime and into that of treason, since they supplied the enemy with sustenance and comfort and undermined the American war effort. Among them was Tyler Porter Shaw of Lincolnville, a sea captain who was supposed to deliver military stores to Maine but instead sold the cargo directly to the British navy. Caught by federal officials, he was rescued by his sword-wielding cousins as he was being transported to trial. He fled to New Brunswick and lived out his days there.

But most of this illegal trade was far more mundane. Surely the farmers in newly created Somerset County who drove their cattle through the woods to Quebec realized this beef was destined for the British army, but high prices and payment in gold soothed any qualms they may have had.

In Eastport, the fogs of Passamaquoddy Bay hid a two-way illegal trade encouraged by British officials in New Brunswick and Nova Scotia. American and British smugglers collected in this remote border town, delivering Virginia flour and other foodstuffs to British agents. The smugglers were paid top dollar for these provisions, which were mostly destined to feed British soldiers and sailors in the Maritimes. If not paid in British gold, the barter often involved goods like cloth and hardware produced in England’s new industrialized cities, such as Sheffield, Birmingham, and Liverpool. Manhattan swells joined Down East fishermen in this clandestine business, often arming themselves in the unlikely event that the largely corrupt local officials decided to interfere.

The Madison administration in distant Washington was well aware of this business, and by late 1812 sent a regiment of troops to suppress it. Led by Colonel George Ulmer, a hard-drinking timber merchant from Lincolnville, these troops had a difficult time chasing the smugglers, who outfoxed them with their local knowledge and bribed them with whiskey or cash to turn a blind eye. On occasion they even kidnapped those soldiers who could not be bought.

Outraged by this conduct, Ulmer used increasingly draconian methods to curtail the traffic, in effect imposing martial law in eastern Washington County. The smugglers conspired to get Ulmer out of the way. Hampered by a tenuous supply system, the colonel had run up large bills with local merchants to feed his troops garrisoned at Fort Sullivan. When he proved unable to pay, the merchants, many of them involved in smuggling, had the sheriff throw the colonel in jail for debt. For almost two months the Machias jail served as Ulmer’s headquarters. Troop morale eroded, and little was done to stop the smugglers. By the time Ulmer returned, his own officers had turned on him and charged him with gross mismanagement and frequent drunkenness. Army superiors relieved Ulmer of command.


What Eastport was to smuggling, Castine was to espionage. The British had been infiltrating spies into Maine since at least 1808, when they sent a young army lieutenant disguised as a Swiss civilian to Castine to determine if the United States was building a fleet to attack Nova Scotia. The lieutenant found nothing, but rumors of spies persisted in Castine and elsewhere. Federal officials even arrested one fisherman who had just returned to Boothbay from New Brunswick. He spent months in Wiscasset’s clammy stone jail until a letter from Washington ordered his release.

The American government also used spies. Deeply concerned about the lively smuggling trade that had quickly developed in Castine and along the Penobscot River during the British occupation, the Treasury Department sent Amos Proctor, who had zealously prosecuted smugglers in northern New Hampshire and Vermont, to investigate. He discovered that British goods worth millions of dollars were pouring into Castine and being smuggled into the U.S. Federal officials from Maine to Massachusetts were alerted, and they impounded many of the goods as they were transported by sleigh westward from the Penobscot River to Portland, Boston, and New York.

Since being tight-lipped was a prerequisite skill for any successful smuggler, much of this story remains a mystery. We will probably never know the full extent of the traffic or who the most successful smugglers were. Those who had been involved in illicit trade with the British were not inclined to talk much about it, and gradually the memory faded, preserved only in dusty but fascinating court records, such as Charles Tebbets’ deposition about smugglers invading his home.

Wake-up calls similar to that loud knock on the door that moonlit night in Hampden were heard throughout Maine and the nation at large. Smugglers were not so much opposing the war as they were providing for their families’ welfare during a time of extreme tension and disorder. Other husbands and fathers did the same when they signed on as privateers in hopes of sharing prizes captured on the high seas.

The government Charles Tebbets represented found it almost impossible to maintain its national honor and will in the face of the people’s crushing economic circumstances and the politicians’ relentless criticism. Mainers seemed to view their situation and their destiny as quite different from that of their leaders in Boston. Just a year and a month after the British lowered their flag and left Eastport in 1818, Mainers — lead by the erstwhile smuggler, William King — voted to form a new state, which was accepted into the Union on March 15, 1820.


Joshua M. Smith heads the Department of Humanities at the United States Merchant Marine Academy in Kings Point, New York.