In 1895 William and Margaret (Maggie) Dingman moved into their new house at 196 Cambria Street with their daughter Wilhelmine and sons George and Arthur. Located on the easterly portion of Lot 509 the house which was built in the summer of 1894 was their second home in Stratford. Following their marriage in 1889 they took up residence at 59 Grant St and their children were born there.

William's father Absalom, a newspaper publisher in Strathroy purchased the Herald, a popular weekly Stratford newspaper, and relocated here in 1886 with his wife, Emma Smith and their family of 3 daughters and 4 sons. He employed three of his sons, William, Lewis and Charles with William, the eldest who had gained newspaper experience as managing editor at the Port Arthur Sentennial, shortly becoming co-publisher. Lewis moved on in 1889 to become managing editor and later owner of the St. Thomas Journal. Although he spent most of his career with that city's newspapers he remained connected with Stratford by purchasing the Herald in 1920 and merging it with the Beacon in 1923. Charles left Stratford to work at the Montreal Star and the Winnipeg Telegram before returning to Stratford to become the first editor and managing director of the new Stratford Beacon Herald in May 1923. After his sudden death six months later his son Charles Dobson Dingman succeeded him.

In 1890 William moved the Herald into a new building designed by architect Joseph Kilburn on the south side of Market Square where it remained until the merger with the Beacon in 1923.
He became interested in the city's civic affairs first as an alderman and later as mayor 1909-10.
He was instrumental in bringing water-powered hydro service to Stratford from Sir Adam Beck's Niagara Power project resulting in the first electric lights being turned on to brighten Stratford's streets on Christmas Eve 1910.  His other activities included a term as President of the Canadian Press Association in 1889.  Dingman Place here in Stratford is named after him.

One of his favourite pastimes was cycling or “wheeling” as it was then known. He would often ride on the cinder paths to places such as Sebringville. Another, more serious interest, was music. He served as an organist at Central Methodist/United Church and helped to compile at least 2 church hymnals.

William and Maggie's daughter Wilhelmine married Arthur Francis, a merchant in Port Arthur, (Thunder Bay) Ontario. Their elder son George served in World War 1 after which he continued in the family tradition as an advertising manager with the St Thomas newspapers. His brother Arthur, became a chemical engineer and located in Montreal.

In 1915 the Ontario government called on William to serve as the Vice Chairman of the newly established Ontario Board of License (Liquor) Commissioners. This position brought with it a role in the administration of the Ontario Temperance Act which came into effect in 1917 so after more than 30 years in the newspaper business he began a new career which meant a move to Toronto. Maggie and William spent the rest of their lives there and are buried in Toronto's Mount Pleasant Cemetery. In an interview as he approached his 80th birthday he commented that his marriage to Margaret McDonough, (Maggie) was the “high water mark of his life”.