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 20th 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.
Jnana's Red Barn 