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.

John Shackford was a Revolutionary War veteran who brought his young family to Eastport at the end of the war, making them one of just six households on Moose Island. For the next half century and a bit more, they were influential figures and then faded entirely from the scene by the turn of the 20^th century. It was a pattern I’m seeing in seafaring families in coastal communities in American genealogy.

His ancestry in America goes back to Dover, New Hampshire, where I lived for 21 years before moving on to Eastport. His father, Samuel, was a mariner who resettled at the mouth of the Merrimack River in Massachusetts, where John was born in 1753 in Newbury, a decade before the port was set off as a separate town, Newburyport.

Among the other children of Samuel and his wife, Mary Coombs, were Mary, who married Caleb Boynton, for whom Boynton Street and Boynton School in Eastport were named; Captain Samuel Shackford, who died in Newburyport; Levi; and William.

As a sailor, John may have visited Eastport as early as 1763, age 10 or so. (As one version goes, “He was brought up a sailor and while so employed his ship visited Eastport, Maine, as early as 1763.”)

Around here, “captain,” as you may be noting, more often referred to a shipmaster than an army rank.

As a soldier in the newly formed Continental Army in its second major military operation, John enlisted in the strenuous march in September and October 1775 through the wilderness of Maine under the command of General Benedict Arnold. Serving in a Captain Ward’s company, Shackford was one of 1,100 men in the arduous trek that saw 300 soldiers turn back and another 200 die en route The surviving troops were left starving and lacking in many supplies and equipment assigned to attack Quebec City.

Joined by General Richard Montgomery’s forces after their capture of Montreal, the Americans attacked Quebec City in a snowstorm on the last day of the year. They were roundly defeated.  Montgomery was killed and Arnold’s leg was shattered.

Shackford was taken prisoner and confined for nine months, six weeks of the time in irons — that is, chained.

After his release, he broke his promise to his captors not to engage in battle. In early 1780 he and instead served under George Washington at Kingsbridge, in Westchester County, New York.

During the Revolution, John’s brother Levi was wounded at the battle of Bunker Hill. More extensive was the service of brother William. First, he was captured on the privateer “Dalton” and confined in the Old Mill Prison in Plymouth, Devonshire, England, for three years; and then, on being released, he served under John Paul Jones and was either killed in action or died from hardships endured in the war — he never returned.

On the other hand, as a veteran, Private John Shackford returned to Massachusetts and married, on November 26, 1780, Esther, daughter of Captain Gideon and Hannah Woodwell. Her father was an extensive shipbuilder at Newburyport.