In his first year as sheriff, Robert Moderwell presided as returning officer at the courthouse for the election of five council members, and for the election of inspectors of “houses of public entertainment,” namely hotels and taverns. Alexander Barrington Orr topped the polls with 77 votes, but William Frederick McCulloch, with just 65 votes, was chosen to be the village's first reeve (1854-1855). A. B. Orr was reeve in 1856-1858, after which, Stratford was declared a town. While the Town of Stratford still had a reeve, and a deputy reeve, it also had a mayor, of which John Corry Wilson Daly was the first, in 1859.
During Robert Moderwell's early time as sheriff, Stratford had some hard financial times. It over-borrowed, and that caused problems for years. The sheriff had to serve a writ on the town for non-payment of debt after the town had borrowed 6,000 pounds in 1852 from the Municipal Loan Fund of Parliament to build a school and a market house and sidewalks. In 1857, it borrowed a further $100,000 to bail out the Buffalo and Lake Huron Railway. Some money was repaid, and interest rates were lowered so that disaster was averted, but a debt of more than $50,000 remained until 1893, long after Stratford had become a city (1885) and Robert Moderwell had died (1886).
As well, in the 1850s there was the scandal of the northern gravel road. While road building was necessary, and the building of this one was a sound idea, it was a project that would lose $100,000, discredit Reeve A. B Orr and bring recriminations down on many prominent citizens.
As sheriff, Moderwell had to become involved. Several times, between 1861 and 1866, the town tried to sell the northern gravel road to the county, and the latter was on the verge of buying it for $5,000 when Sheriff Moderwell stepped in and seized the road for the benefit of creditors. When it went on the auction block, the county got it anyway, for $4,850.
The Beacon in its issue of July 6, 1866, reported that “the sheriff did the town a good deed last Tuesday in ridding it of the northern gravel road.” There were no winners except the people now served by the road.
But life was not all business for the sheriff and his community. Sports were popular, among them cricket, of which there games played regularly in the 1850s most notably between Stratford and St. Marys. Robert Moderwell was president of the Stratford club, whose membership fees were $3 annually. The game was so popular, it became part of the athletic program at schools and there were exchange games between Stratford Grammar School and the Victoria Club of Mitchell. Moderwell was also president of the Stratford Agricultural Society (1864-1869), as noted by Dean Robinson in his book Reflections: A History of the Stratford Agricultural Society 1841-1991.
Moderwell retired as sheriff in 1872. Before his death, in 1886, a biographer writing about his successor, John Hossie (see Hossie Terrace) had this to say of Moderwell: “The predecessor of Mr. Hossie in the office of sheriff, was Robert Moderwell, the first sheriff of Perth, taking the office when this county was set off from the district. He is yet living in Stratford. He was for years very prominent in the local agricultural society, and still takes a lively interest in such organizations and interests.” Source: Adelaide Leitch, Floodtides of Fortune; Stanford Dingman, Streets of Stratford, a series of articles for the Stratford Beacon Herald; Compiled by Gord Conroy
Robert Moderwell's son Andrew had a managerial position with the Bell Telephone Co. in Stratford (see Albert Street). Many members of the large Moderwell family continued to live in Stratford. This photo of Moderwell sisters was taken in about 1910.