Weiland began playing junior hockey in Seaforth, where he spent three seasons with his hometown team. In 1923 he moved to Owen Sound, Ontario to attend school, planning a career as a druggist. He joined that city's junior team, the Owen Sound Greys, and led them to the 1924 Memorial Cup as Canadian champions. He was the club's top scorer with 68 goals in 25 games. Cufflinks presented to Weiland after Owen Sound's Memorial Cup win in 1924 are part of a permanent junior hockey exhibit at the Hockey Hall of Fame in Toronto.