James was born to James and Frances Magdalena Griggs Flanagan on a Saturday, He was the fifth child and second son of the couple, taking the name of his father and the maiden name of his paternal grandmother.

James was enumerated as five years old in the 1850 census. His father lists himself as a boatman, probably working for the Flanagan farm and quarry. James' three older sisters attended school within the year.

James' was only almost 9 years old when his father was murdered by one of his own employees on a Wendesday near Bakerton. James' father had inherited his grandfather's empire only a year earlier.

By 1860, an 11 year old James is enumerated in his recently widowed mother's household in Harpers Ferry district (near Bakerton). James and three of his siblings, William, John, and Alice, had all attended school within the year.

On a Thursday, James married Miss Mary Ellen Caton, daughter of George Walter and Margaret Ann Hunter Caton. Mary's father consented to the marriage in person. The couple was married by the Rev. William Gwynn Coe, a Presbyterian minister.

James and Mary Ellen's first child, Martha Lee, was born on a Tuesday. A birth record has not yet been found. A few records favor an 1869 birth year, which would put Martha as being born before her parent's marriage in September. According to the 1870 census, she was just one month old and went by the name of Lucy.

A 22 year old James and a 21 year old Ellen were enumerated in the 1870 census on a Tuesday, alongside their one month old daughter, Lucy [Martha Lee]. James is currently working in the stone quarry. Neighboring his household is his soon-to-be son-in-law's father's household, Thomas Welsh, and his grandmother, Martha Flanagan.

James and Mary's second child, Annie Frances, was born on January 10th, sometime between 1871-1873. Given the birth years for the previous and next children, Annie was most likely born in 1872. A birth record has yet to be found.

James and Mary's daughter, Margaret "Maggie" Virginia, was born on a Tuesday in Bolivar district, near Bakerton. James lists his occupation as farmer.

Determined to quit farming and solely operate the Flanagan Quarry, James holds a public sale of his farm equipment and livestock at his residence on the Daniels (old Flanagan) farm.

On a Monday, the couple's fourth daughter, Essie Katherine, was born.

James and Mary's first son, Charles William, was born in October of 1877 in Bolivar district, near Bakerton. James lists his occupation as laborer.

A 32 year old James and his small family are enumerated in Bolivar district on a Saturday. James lists his occupation as both farmer and laborer, likely working both the Flanagan farm and Flanagan quarry.

On a Tuesday, the couple's second son and sixth child was born. They named their son Walter Jerome.

On a Saturday, James and Mary's seventh child and third son was born. They named their son James Alvey.

Sometime during the month of March, 1886, Mary gave birth to a son, whom they named John Griggs.

The couple's ninth child was born in September of 1888. They named the little girl Berna A.

On a Friday, the couple's youngest daughter, Berna, died from an alleged cold. She was only one year old.

James and Mary's tenth child, Oscar, was born on a Wednesday near Bakerton.

James' mother, Frances, died on a Thursday at the home of his sister, Alice. Her health had been failing for many years, however it appears that she never recovered from an illness that she was stricken with early of that year.

The Shepherdstown Register reports a break-in at James' residence. The thief appears to have stolen his grandfather's, William Flanagan's, pocket watch -- an old-fashioned silver watch with the initials W. F. engraved upon the case. Also stolen were about 5 dollars, a half dozen fine handkerchiefs, a various other items. It was noted that a reward would be given for return of the watch, however nothing was ever reported about its return.

The Shepherdstown Register reports that James' wife and daughters surprised him with a 50th birthday feast. Some 60 or 70 persons were in attendance. The paper reported that the dinner was fit for a king and included chicken, turkey, being extremely bountiful. After dinner, Rev. J. L. Kibler rounded up the children and baptized several of them. It is noted that James' was asked several times to celebrate his birthday much more often, and that the guests wouldn't have objected to celebrating it monthly.

James' name was drawn from a list of petit jurors to appear on Wednesday, the second day of the February term.

The Shepherdstown Register reports that James entertained Mr. A. Young and Mr. H. Shaffer of Middletown, Maryland, and many Harpers Ferry friends.

James was widowed on a Wednesday, after his wife was quickly stricken with apoplexy. According to reports in the Shepherdstown Register, she died surrounded by her family. James buried his beloved wife in Elmwood Cemetery in Shepherdstown.

52 year old James was enumerated in Harpers Ferry District (near Bakerton) on a Thursday. He lists himself at married, having been married 30 years, and his occupation as farmer. His son, John Griggs, is attending school.

Martha Daniels Link and Cora Daniels Moler appear to have sold their interests in the Flanagan Quarry to Washington Lime. The interest totaled about 36 acres. Martha and Cora were James' cousins, daughters of Ann Rebecca Flanagan Daniels, a sister to James' father.

James gifts the Register office with a basket of "Abundance" plums. George Duke must've said that his plums were better in taste or appearance, as the office asked him for samples as proof.

A Bakerton resident wrote to The Shepherdstown Register, believing that Bakerton should carry the prize for large hogs. James killed two very large hogs, one weighing 505 and the other 415 pounds. Other residents mentioned were John Welsh, G. T. Trundle, Albert Rice, G. Newton Moler, Arthur Moler, Issac Kidwiler, and Robert Duke.

It is reported in The Shepherdstown Register that James' son, John Griggs Flanagan, killed 80 snakes while working James' farm. Neither the size, nor type, of snakes were mentioned.

The aid society of Bethesda Church held a silver tea (fundraiser) at the home of James.

James is named as having butchered the largest hog in the Bakerton neighborhood, at 587 ½ pounds.

James is named as a newly appointed trustee of the Bakerton sub-district of Harpers Ferry. Other appointees named are: D. R. Houser, Keller, A. M. Best, B. Edwell Maddox, and N. V. Engle.

James butchered 10 hogs, averaging about 272 pounds each. The heaviest was 492 pounds. James' son-in-law, Thomas Welsh, was considered the boss butcher.

On this Friday night, James lost a horse he considered rather valuable, when she hung herself with her halter chain. He states that this is the second horse who has died in the same manner in the same stall.

James notes that his three cows yielded 68 pounds of butter during February, 1910. He says this is after feeding two calves and providing milk for a pet lamb.

James served as a juror during the May, 1911 term of the circuit court.

When James' father-in-law, George Caton, died intestate, James was a legal heir to his property. Caton's real estate was located east of Shepherdstown bordering the Cement Mill Lot on what is now River Road. This property was sold by James and other heirs to Robert Miller in consideration of $600.

James tells the Shepherdstown Register that he believes he could challenge the weight records for young hogs. The register reports that James butchered six Duroc and Poland China hogs, which weighed 137, 140, 169, 118, 128, and 151 pounds

Mr. M. M. Burke, of Washington D.C., and his three daughters, Katie and Irena Burke, and Mrs. Hannah Knox are visitors of James.

James rode aboard the engine to make the first trip across the new railroad track which was laid to carry the output of the old Flanagan Quarries to the Bakerton Quarry of Standard Lime and Stone. D. R. Houser, Daniel Lee Moler, and Albert Rice were also present.

The Shepherdstown Register reports that James killed two unusually large hogs -- the weights of which were 468 and 452 pounds. James supplied the register office with a generous supply sausage as a gift.

James' son, Walter Jerome Flanagan and his wife and son, of Strasburg, visited James at his home the past week. Miss Nellie Hunter, of Stephens City, was also a guest. Nellie was likely a relative of James' late wife.

James makes the trip to Baltimore to visit his son, John Griggs Flanagan and family, who is living there.

It is reported that Mr. D. Sidney Smith, Mr. and Mrs. Fred Smith and their daughter, Mary, of Frederick, drove to Bakerton on a Sunday to spend the day with James. Could this Smith family be of relation to James' grandmother, Martha Smith Flanagan?

The Shepherdstown Register reports that Mr. and Mrs. James Knock and Mrs. Hannah Knock, of Washington D.C., are guests of James Flanagan.

James died on Monday, December 4, from a "compilation of diseases that baffled the skill of all physicians", according to his obituary. He had been in failing health for one year and confined to his room for 2 months. Rev. Absalom Knox officiated his funeral. He was buried beside his late wife in Elmwood Cemetery at Shepherdstown.