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.