The progenitor of this family was Simon William Riley, possibly from Northern Ireland, whose first appearance in this area we find in St. Luke’s Anglican Records when he married Elizabeth Balsor in 1816. In the 1827 census we learn that he was a carpenter, belonging to the Church of England. A transaction of 1829 tells us that he lived, for a time at least, on lower St. George Street in Annapolis Royal, although in the1838 census he was listed, with a household of 13, in Clements Township. When he sold a piece of property in 1841, he was living in Granville. He was buried in the Garrison Cemetery in Annapolis Royal after his death in 1855 at the age of 63.
The next generation of the family appears as Methodist, Simon’s sons Simon, Jr. and Andrew having been baptized in that church as adults. Two of Simon’s daughters and two of his sons married and made their homes in Annapolis Royal. Ellen Riley married Charles Starratt, a merchant in Annapolis, and Dorothy Riley married Simon Bishop. Simon William Riley, Jr. married Sarah Jane Starratt. Simon, Jr was listed variously as a carpenter, port warden and shipyard master. He owned the property on the southeast corner at the lights in Annapolis for over 50 years, now owned by Alison Thomson. His son Simon, who married Mary Esther Lenehan, was employed by the D.A.R. (Dominion Atlantic Railway), working his way up from locomotive cleaner to locomotive engineer; he and his family lived at 204 St. Anthony Street.
Simon, Sr.’s son Andrew Riley, who married Isabelle Hardwick, was also a carpenter, and was actively involved in the residential and commercial construction that was taking place during the latter half of the 19th century in Annapolis. In 1876 he built a house for the druggist, Dr. Cunningham, on St. Anthony Street, referred to as an “elegant bijou French cottage” in the Nova Scotia Farmer & Annapolis County Times, the local paper of the day. In 1875 he built a new livery stable at the Queen Anne Inn after the old one had been destroyed by fire. Andrew and his family lived at 95 Victoria Street.
Andrew’s son James Andrew Riley, known as Andrew, married Margaret Miller. They, too, lived at 95 Victoria Street. James Andrew also followed the construction trade. In 1919 he was responsible for erecting the 85’ high smokestack and the boilers for the evaporator (for drying apples) in the plant that used to exist on Chapel Street. He had a large family, including six sons (Fred, Bob, Charlie, Clinton, Wilfred and Frank) who were avid hockey players. In the 1920s they had their own team, coached by their father. Fred Riley, a veteran of WWI, was the Chief of Police in town for a number of years, and later the Fire Chief. Frank Riley had a car dealership on St. George Street at one time. Charles Riley and his wife Hilda lived for years at 46 Drury Lane.