Eastport fell under British control in 1814 and was then attached to Canada for four years. Not that it went quite that easily.

As the conventional story proclaims, Captain John “commanded the first militia company organized in Eastport, his uniform consisting of an old Continental three-cornered hat, and he wore an old sword. His company was made up largely of veteran soldiers of the revolution, a wild set of fellows whom their captain found it difficult to control.”

More descriptively, in William Henry Kilby’s history volume, as Shackford’s grandson Samuel contended, “His men were of a sturdy, wild set of fellows, who appeared to think that the first duty of a soldier on training days was to drink toddy; and their captain had a hard enough time to control them. Many of them, having served half-clothed and half-fed in the Continental Army, doubtless felt that they had earned the right to an occasional frolic.”

I won’t question his sources, but he neglects to mention that Fort Sullivan and its commanding officer surrendered without firing a shot, as did Castine, Machias, and a fourth Downeast town. Still, continuing the Shackford account,

“When the British fleet captured the island and the commodore came on shore to take possession of the island, Captain Shackford met him at the shore, carrying a goad stick in his hand,” not the old sword, mind you, “and addressed him thus: ‘Well, sir! What brought you here? I am King of this island, and these are my subjects. If you behave yourself, you can come on shore. If not, you had better be gone.’ The commodore politely assured him that he had called on business, and trusted that he should conduct himself in a manner becoming a gentleman and to the satisfaction of his Majesty.”

Goad stick? Like for cattle? Captain John apparently had a flair for drama, as the next incident illustrates.

“After the English had taken possession of the town, all of the inhabitants were ordered to swear fidelity to the King, or leave the town and have their property confiscated. But the old soldier, when summoned to appear and take the oath, replied to the officer that he had fought under General Washington; that he might take four horses and draw him in quarters, but never would he swear allegiance to the King of England. It was probably on account of his eccentricity and boldness that the old gentleman was excused from taking the oath and allowed to retain his property.”

Follow that? Who would you nominate to portray Captain John in the movie? And, for that matter, the Brit? It’s still a great scene.

Beyond that, Lorenzo Sabine, editor of the Eastport Sentinel, later contended, “No privateer was owned here,” though Eastport was subject to heavy privateering (state-sanctioned piracy) during the War of 1812. The British cruiser Breame took prize of the Delesdernier with master John Shackford junior and Samuel Wheeler, an owner on board as a passenger. They paid ransom for their property and were released.

Another ship, commanded by Captain John’s son William and sailing from Eastport in early 1812 with a cargo of rice and flour, was captured 25 miles from the port of Cadiz, Spain, by three French privateers. He and his mate and cook were left destitute.

Another prize was a chebacco boat with Captain John’s sons Samuel and Jacob Shackford, who paid a stipulated sum and were given up. The chebacco design, by the way, was a little two-masted boat, popular among New England’s inshore fishery, originating during the Revolutionary War. They were built by the hundreds and averaged from 24 to 48 feet in length, had two masts and no bowsprit. They were usually a flush-deck vessel with several cockpits, or “standing rooms” in which the fishermen stood to fish. A middle hatch gave access to the fish hold. They were also almost always built near the dwelling of the builder and sometimes no more than a few yards from the front door. Shackford Cove, then?

The third time John junior was taken prisoner was when the Delesdernier was captured off Cape Ann, Massachusetts. He and companion brother Samuel were taken to Halifax, Nova Scotia, where he was left without a hat and, one dollar excepted, entirely destitute in the streets.

Captain John’s son-in-law Darius Pearce/Pierce, in command of the schooner Sally, better known as Old Sal, was taken by the frigate Spartan and taken to St. John, New Brunswick.

Quite simply, the War of 1812 hit the Shackford family heavily. At one time, John and Samuel Shackford and Darius Pierce were all held captive by Lieutenant Blythe, who then released them.

All of it, of course, has relevance on the house we bought, as you’ll see.

After the close of the Revolutionary War, and by then disgraced as a traitor, Benedict Arnold took refuge among the Loyalists in neighboring St. John, New Brunswick, where he emerged as a merchant and shipowner. Once, he personally directed the work as Captain John Shackford and presumably a crew loaded a vessel at Campobello Island.

Shackford later recalled,

“I did not make myself known to him, but frequently, as I sat on the ship’s deck, watched the movements of my old commander, who had carried us through everything, and for whose skill and courage I retained my former admiration, despite his treason. But, when I thought of what he had been, and the despised man he then was, tears would come and I could not help it.”

The Loyalist impact on Eastport, as I’m seeing in this project, was immense. Neighboring St. Andrews, New Brunswick, and St. John further up the coast were both founded in 1784 by Loyalist families exiled after the American Revolution. Many of them later filtered back into Eastport, including some lines that owned our house.

All of it, of course, has relevance on the house we bought.

Eastport’s growing community’s land claims needed to be clarified.

As Jonathan D. Weston notes in Kilby’s history, the Massachusetts legislature on June 17, 1791, authorized the survey of Moose Island, or Eastport, “the inhabitants prior to that time being simply ‘squatters,’ without titles to the land they occupied. The effects of this shiftless, temporary condition of affairs lingered for some time afterward.” Solomon Cushing then assigned lots to the occupants in 1791, according to Kilby. At the time, Eastport and Lubec, as Plantation 8 or Township 8, had a population of 244 people.

The deed John Shackford received from the Commonwealth of Massachusetts opens with the date June 18, 1791, and describes the committee appointed to “survey and lay out the [plan] of the settlers within said township one hundred acres of land to each settler to include his improvements,” as well as additional public lands to support a church and a school. Each settler who arrived before January 7, 1784, would pay the state five dollars for their property, while those who came later would be charged ten dollars. The purchasers would be exempt from any state taxes for five years.

Fitting “a plan of that part of said township called Moose Island with the several lots delineated thereon that Captain John Shackford a settler,” received lot No. 3, one hundred acres. The agreement was dated August 14, 1793, and recorded in Boston September 20.

His brother-in-law, Caleb Boynton senior, received lot No. 4, also one hundred acres. While his document was also dated June 18, 1791, it was not recorded until August 30, 1804.

Lot No. 17, 50 acres, went to Caleb Boynton junior in 1804.

The Shackford property would stretch along the waterfront from the middle of Shackford Cove to what would become Key Street and then back to County Road. Boynton’s stretched from Key Street to Washington Street. Together, their holdings would encompass about half of the business and residential lots of the eventual village.

The 1790 Census had a single Shackford household, John’s, with one free white male over 16, four under 16, and one free white female. This was recorded next to Caleb Boynton, with two white males over 16 and four females. Further down the list, Caleb junior had one white male over age 16, one under, and two females.

Curiously, in 1800, it was only one Boynton, Caleb senior.

You will find holes in the Census data.

Among non-family dwelling with Shackford around then was an unmarried Englishman, James Carter, in 1789. Quarters must have been tight.

With the deeds, the occupants became landowners rather than remaining squatters. Five dollars, do note, was a substantial amount at the time. Whether it was “reasonable” can be left to debate.

Thus, in 1793 Shackford gained clear ownership of one hundred acres at Shackford Cove, being lot No. 3 — and within that, the plot that includes our house. How much earlier he had built here becomes the question. By 1783, as his fee would indicate? Not all of this land went to farming, and he obviously augmented his holdings over time. If he was building ships, he definitely needed timber, which might explain the Shackford Head connection.

While I’ve been unable to find the deed of Shackford Head, it’s clear that Captain John acquired a hundred acres there, too. There are tales of the box of unsorted early documents at the courthouse.

The transactions I’ve found do undermine a story about a sheriff arriving from Massachusetts in 1797 with an armed party to seek payment for the lands. Remember, Maine was a district of Massachusetts until 1820. After being roughed up, and with what may have been a revised approach, the sheriff offered deeds from the state at a reasonable cost plus a five-year tax exemption.

Of Captain John and Esther’s children who survived to maturity, all four sons became ship captains, and two of their three daughters married likewise. Many of the grandsons continued that legacy.

Can you imagine the life in this house at the time?

John Shackford senior definitely explored what would become Eastport in 1782, and, as one account expressed the encounter, “determined to remain and make provisions for the safety and comfort of his wife and children preparatory to permanent settlement.”

The early years of Eastport and its Moose Island are generally fuzzy. Legally, the pioneer white inhabitants were squatters. Captain John initially settled at Broad Cove at the neck of what became known as Shackford’s Head, and soon afterward built a mile-and-a-half away, at the edge of today’s downtown and what was soon known as Shackford’s Cove.

In one version,

“The Shackford family originally settled on Shackford Head, where Revolutionary War veteran Captain John Shackford began a homestead in 1783. … He built accommodations for curing the fish he hired caught by the Indians and some white fishermen … He also erected a strong storehouse of logs, where he kept and sold such merchandise as met the requirements of the fishermen and Indians; the fishery and storehouse were in full operation, and he set about building a dwelling house and planting part of his farming lands. Everything being ready in 1784, he set out in his small sailing vessel, the Industry, for Newbury, and brought to their new home his wife and two children, John and William Shackford.”

The Indians, mind you, were Passamaquoddy, who are still vital component of the community.

In the other version, “In 1787, having built a dwelling-house near the shore, at the foot of Shackford Street, he brought his family, consisting of wife, sons John and William, to their new home in the wilderness …” Not only is the date different, but also their address or its equivalent.

As I said about fuzzy? The consensus for the Shackfords’ arrival seems to be 1783/1784, the end of the Revolutionary War.

Jonathan D. Weston’s recollections had the Shackfords as one of the first six white families in town, arriving in the spring of 1784. Five years later, Weston calculates, the number of households had increased to 22 or 24, “the heads of one-half of these families were either men of English birth or those who had adhered to the royal cause of the war.” Either way,

“John’s little craft was the first vessel owned in the place, as the fishing business up to that time had been done in open boats. Among the vessels subsequently owned by him were Delight, Hannah, Sally, and Patty,” two of them apparently named for his daughters. Patty, meanwhile, “plied between Eastport, Portland and Boston, and was the first freight and passenger boat employed on this route. She was commanded by his son, John.”

While that jumps ahead in our chronology, it does reflect the family’s identity as shipmasters and perhaps also shipbuilders. Shackford Cove wound up with four shipyards along its short shore.

From the start, even before being named Eastport, the small frontier community on Moose Island comprised of a handful of families gained a reputation for “sheltering and sharing the gains of adventurers, smugglers, and gamblers.” Not to cast a shadow over the Shackford family integrity, right? Or making a nice profit?

Welcome to America’s Wild East.