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John O'Brien 
ohn O'Brien was born in 1750, probably in Ireland, and like his compatriots the Shearman brothers was one of the earliest merchants in Penn Yan. He bought two acres from Morris F. Sheppard in 1808 and built a house on it that was surrounded by a picket fence. He also ran a store out of the same building, which became the first home of Cornelius Masten and his family when they arrived in 1817.
O'Brien and his family are shown on the 1810 census in Penn Yan. At that time there was in this household one male over 45, who would have been John himself; and one male under 10, who would have been his eldest son John; two females between 16 and 26, one of whom would have been his wife Betsy, and two under 10, presumably two daughters.
By 1820 there were more children in the household, which was near Penn Yan but probably not within its borders; the adjacent household was that of Froanna Allen, Gideon Allen's widow, for whom "Widow Hill" was named, going northwest out of Penn Yan. The O'Brien household contained one male over 45, John Sr., who was 70 years old by then; and one male 10-16, John Jr.; and a boy under 10; one female 26-45, Betsy; two aged 10-16, presumably the same two daughters already in the household in 1810; and two girls under 10.
The family is not listed on later censuses, but since until 1850 they only named the head of household, this only shows they were living with someone else. Considering John's age this is certainly a reasonable supposition. They seem to have stayed here, as evidenced by the fact that the elder John was buried in Lake View Cemetery when he died in 1832; and his son and grandson, also named John O'Brien played significant roles in the commercial and social life of the village.
John O'Brien Jr. was born in the house on Main Street in 1810, and later married Lucy Ann Worden. They had six known children, all born in Penn Yan:
- John H., born in 1842, married Lizzie Douglas, who died at the age of 26 in 1876; married second Kate Savage, by whom he had two daughters;
- Charles E., married Mary Campbell and had a daughter, then went to Colorado and disappeared;
- Pamelia Swarthout, who died after bearing a son, Eddington Swarthout;
- Helen Eliza Wheelock, wife of Silas Wheelock;
- Lucy Ann Hicks, wife of Henry A. Hicks; and
- Harriet Lewis, first wife of Leon Lewis. When she died in Rochester in May, 1878, she left her property to her husband and appointed him her executor. A clause in her will states that he "has for years considered the family, including my immediate relatives, as his own; that he has at all times given freely of his money and substance for their benefit, and that I have no doubt that my said husband will continue his kind offices to my kin in the future, as he has heretofore shown them in the past; but [he] has carried his generosity to others to the extent of embarrassing himself...." In the upshot, Lewis turned all his wife's personal estate into cash, fled to New York and then to England with a host of creditors and his dead wife's family on his heels once it was found that he had left the country with her niece, a minor. Their home in Penn Yan was on Liberty Street, now the rectory of St. Michael's parish; the elaborate and elegant carriage house stood behind it, and was moved across Keuka Street for use as a convent; it still stands there today, next to the brick schoolhouse.
O'Brien was associated with:Land plots:
Sheppard's first purchase
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