The name is of English origin, and the first one to settle in this country was Benedictus Alford, as the name then appeared, who made his home at Windsor, Connecticut. He was a sergeant in the Pequot war in 1637, a juror in 1643, and constable of his town in 1666, when a day of special thanksgiving was observed throughout the colonies. He was a member of the Windsor church. When his will was offered for probate in 1683, his estate was valued at two hundred and twenty-nine pounds, three shillings and six pence. This was considered a large amount in those days, and Mr. Alford was looked upon as one of the most prominent and influential citizens. He was married to Miss Jane Newton on November 26, 1640, and the following named children were born to them: Jonathan, born June 1, 1645; Benedict, born July 11, 1647; Josias, born July 6, 1649, who inherited the form granted to his father for services in the Pequot war; Elizabeth, born September 21, 1651; and Jeremy, born December 24, 1655.
Jeremy was the youngest son of Benedictus and Jane Alford, and the first name of his wife was Jane, who survived him and was administratrix of his estate in 1709. Her death occurred in 1715; nine children were born to them, namely: Benedict, Newton, Jonathan, Jeremy, Jane, Joanna, Elizabeth, Elizabeth (2) and Job Alford.
Job, the youngest son of Jeremy and Jane Alford, was born August 26, 1708, and about 1734 became one of the first settlers of Harwinton, Connecticut; his children were Job and John Alford.
John, youngest son of Job Alfred, was born September 4, 1738, and he was joined in marriage to Lydia Fellows; six children were born to them: Eunice, Polly, Joanna, Consider, William and Benjamin Alford. Benjamin, youngest son of John and Lydia Alford, was born March 26, 1769. He was married to Miss Elizabeth Chapin, and the following children were born to them: John B., who died in infancy; John B. (2); Samuel D., who also died in infancy; Samuel D. (2); and Elizabeth Alford. The father of these children was a resident of West Springfield, Massachusetts, subsequently removing to Westfield in the same state. He was engaged in the West Indies trade, and was a large dealer in ivory; on one of his return voyages he landed in Savannah, Georgia, to attend a sale of ivory, and contracted yellow fever, from which he died. His second son, John B., was united in marriage to Miss Hannah Hopkins, who bore him four children, namely: Elizabeth; Caroline; John B., who died in infancy; and John B. Alfred.
Samuel D. Alfred, youngest son of Benjamin and Elizabeth Alfred, was born June 14, 1804. He was eleven years of age when his father died; he remained at home with his mother and elder brother, assisting with the work on the homestead farm until he was sixteen years old, when he went to Hartford, Connecticut, and became an apprentice to a cabinet-maker. After acquiring a thorough knowledge of the business he worked as a journeyman in Batavia and Lansingburg, New York, and in the latter named city he was united in marriage to Miss Sally Willard, who was born September 30, 1805. Two children were born to them: Benjamin C. and Roxana, the latter of whom died in infancy. Mrs. Alfred died November 25, 1828, and mr. Alfred committed the care of Benjamin C. to the care of his grandmother, who resided in Westfield, Massachusetts. Mr. Alfred then engaged in the sale of clocks, traveling with his wagon as far north as Montreal, Canada. His business soon became so prosperous that he placed a number of traveling salesmen on the road, and he continued at this line of work until he formed a mercantile association with Almon Smith and Lucius Wheeler at Berkshire Center, Vermont. He retired from the firm in 1840, and removed to West Haven, Vermont, where he was in business for two years, subsequently removing to Fairfax, where he established himself in business, and continued to reside there until his decease. In 1865 Mr. Alfred retired, transferring his business to his son, John B. Alfred. Mr. Samuel D. Alfred was one of the prime movers in procuring the removal of the Newhampton Institution from Newhampton, New Hampshire, to Fairfax, Vermont. For many years after its removal he gave largely of his means and time to its support. It was one of the leading schools of that time. Mr. Alford gave all of his children a good and thorough education, and contributed liberally of his wealth to enable them to make a beginning in life. He was a man of the strictest integrity, and had the reputation of being the soul of honesty in all his transactions. Mr. Alfred, on November 25, 1832, married for his second wife Miss Polly Smith, who was born in Fairfield, Vermont, August 22, 1812. Ten children were born of this union, namely: Samuel D., Jr., who married Cerepta B. Freeman, and died at the age of forty-eight years; Pamelia Ann, who is still living; Mary Celinda L., wife of Charles E. Fisher; Sarah M., wife of Elbridge D. Richardson; Cromwell B., who married Jane Roberts, and died at the age of forty years; Elizabeth C., who died at the age of five years; John B., who married Susan A. Bradley; Almon S., who married Lucy A. Ives; Chauncey Chapin, who married Ann Chase Hunt; and Frank E. Alford.
This genealogical sketch is taken in its entirety from Genealogical and Family History of the State of Vermont: A Record of the Achievements of Her People in the Making of a Commonwealth and the Founding of a Nation by Hiram Carleton, published in 1903. (Source) The information is provided as written in the book with the disclaimer that the book has no source information or footnotes. I can vouch for most or all of the information after Benjamin Alfred and Elizabeth Chapin, while the information regarding prior generations up to Benedictus Alford has not be verified.