In that election he was again elected to a two-year term, finishing first of seventeen candidates, but this time resigned one year into his term in order to run for mayor in the 1905 election. May's time on council included the time in which Alberta was incorporated as a province; as an alderman he voiced his support for a lavish celebration to be in Edmonton, which was to be the capital city of the new province. While sitting on council, he also voted against a proposed bylaw that would have permitted suffrage for women in civic elections; he had initially voted in favour of the law, but had later reconsidered and reversed his vote, effectively killing the bill. The vote previously had been in favour of the bill, by a margin of one vote. As the popular choice leading into the election, he handily defeated fellow councillor Arthur Cushing by a count of 627 votes to 355, and thus became mayor of Edmonton. He served in this capacity for one term of one year, but did not seek re-election in 1906 and retired from political life thereafter. It was during May's term as mayor in which the municipal foundations of Edmonton were set; he oversaw the purchase of the road maintenance equipment, the city's first telephone system as well as the upgrade of the street car system to steel rails and posts, purchase of land for municipal use, paving of roads, and negotiations for the establishment of a manufacturing plant in the city. He also travelled to Toronto to lobby for a new union railway station in Edmonton to be constructed for use by the Grand Trunk, Canadian Northern and Canadian Pacific Railways. It was also during May's term which the Alberta Legislature Building would first open its doors, which he would participate in its opening ceremonies. In 1911, he would be named a returning officer for Edmonton, in charge of overseeing the 1911 Canadian federal election. May was active with the Masonic Order, the Presbyterian Church, and the Liberal Party of Alberta. He also was a member of the Edmonton Exhibition Association, Old Timers' Association as well as a director and manager with the Alberta Lumber Company, founder and president of the Edmonton Kennel Club, and one of the founders of a local contractors' association. In 1906, May was involved in the planning of the first provincial fair in Alberta. May married Ann Galbraith at Saugeen, Ontario in 1882; they would have two children and remain married until she died suddenly in 1897. He remarried in 1901, to Margaret Henderson with whom he had three additional children.