I’m presuming that the house Jonathan Delesdernier Weston recollected as town’s second conventionally wood-framed house, built after 1812 but removed shortly before 1888, was John junior’s. The 1855 map shows a J. Shackford house at the southeast corner of Water and Middle streets that doesn’t match current buildings. Weston, incidentally, built the 1810 Federal-style house at the corner of Boynton and Middle streets, a place now noted as housing John Jacob Audubon on his residency in town.
The Eastport Sentinel in September 8, 1880, noted, “The close observer, as he walks about town, notices many changes and improvements within the past year. … It is of the fixing up that we all speak particularly. The John Shackford house on Water Street has been repaired and remodeled by Mr. Warren Brown so that it bears little resemblance to its former self.” Brown was a tailor and fish packer with a growing family, and the John Shackford in question would have been dead 12 years. As a further complication, among the residences destroyed in the 1889 fire was Brown’s.
John junior’s first son, Benjamin Batson Shackford (1811-1884), most likely
spent his early life “aboard his family’s ships training for his shipmaster’s qualifications,” as Joanne Shackford Parkes wrote in the Shackford Family History blog. “In 1833, when he turned 21, he married Harriet Bibber, daughter of Thomas Bibber and Dorcas Pettengill. They made their home in Eastport and had eight children.
“Seventeen years later, the family was doing well financially as reflected in Benjamin’s 1850 Census report of having property valued at $1,400. By then, Benjamin, the sea captain of the brig Waredale, was traveling to Baltimore, St. Thomas [Virgin Islands], and Trinidad.”
She found that in 1855, newspapers reported the Waredale and Shackford sailing from Norfolk to St . Croix in February; Guayanilla, Puerto Rico, to New York and then St. Thomas in May; Maracaibo, Venezuela, to Eastport in July; and Eastport to Calais and then to Bathurst, Africa, in October. She adds to that his sailing multiple times between 1856 and 1858 to Trinidad, bringing back molasses. And in mid-1858, he added South Carolina; the Turks; Mobile, Alabama; Surinam; and Matanzas, Cuba, and Remedios, Cuba, to his rounds.
The 1860 Census valued his real estate at $1,200 and his personal assets at $400. That year, as Parkes wrote, he sailed on multiple trips to Puerto Rico, up and down the New England coast, and to the Turk islands. By 1863 he was sailing the Waredale frequently to Jamaica and Cuba.
She then describes how in 1864, on his second trip as captain of the bark Zelinda from Matanzas or New Orleans to Philadelphia (reports vary), he was overtaken and boarded by the Confederate privateer ship Florida while off the coast of South Carolina. The crew was placed aboard another captured ship, the schooner Howard and sent back to port while the captain of the Florida set fire to and destroyed the Zelinda. “It appears that the crew was not allowed to take much with them, and after the Civil War ended, Capt. Benjamin B. Shackford filed a claim in the Alabama courts reporting that he had lost his belongings, and in 1875 he was reimbursed $2,303.85 for his losses. In 1883 he gave a deposition stating that another member of his crew had also suffered a loss of clothes, outfits, and articles.”
She notes that when Benjamin’s father John died in 1866 without a will, he left properties valued at $3,200. “The probate dragged out until 1872 and finally resulted in a division of the land which included some prime real estate in Eastport which was divided between Benjamin and the families of his siblings, Charles William and John L. Shackford.
“This increased Benjamin’s real estate holdings significantly and, in the 1870 census, he reported real estate valued at $3,000. The American Bureau of Shipping lists him as the master of the L.L. Wadsworth around that time and newspaper articles show him sailing to Freeport and Trinidad. While his last trip on the L.L. Wadsworth was around 1872, Benjamin continued to list his occupation as sailor in the 1880 Census.
After a life of sailing and adventure to many places in the world, Benjamin Batson Shackford died in Eastport in 1884 at the age of 72.
His children were Joshua Shackford (1834-?); John Edward Shackford (1836-1862), blacksmith, died in New York; Harriet Elizabeth Shackford (1838-1861); Marietta Shackford (1840-?), married Joseph R. Gilman; Ann Pearce Shackford (1841-1924), married Andrew V. Bradford, moved to Oregon by 1900, died in Oregon in 1924, gravestone is in Eastport, Maine;
Emma Shackford (1842-?); Gertrude Shackford (1844-?); and Stella Woodwell Shackford (1853-1918), married William Pearce Higgins, died in Oregon.
Remember, John junior grew up in the house we now own.
Jnana's Red Barn 
Read this nice summary of Capt Benjamin Shackfords while doing a deeper research about him as I work on updating my blog about him. Had me thinking of you living in one of their homes and spending time researching and writing about this experience. Also found an article in Old House Dreams about Benjamin’s old home at 10 Shackford St that you might be interested in – it describes the property & has some pictures. Also want to say that I appreciate your writing style – it tells the story of this seafaring captain’s life in a descriptive and reflective manner that helps us know that seafaring was his life. Joanne Shackford Parkes
Thank you, Joanne. Your own work has been very helpful in my efforts to unravel the family’s history here. You may have noticed my interest in their involvement in Dover, New Hampshire, where I previously resided. As you know, in both places, too many unanswered questions linger. Onward, then!