Bert Oldershaw began canoeing in 1939 with the Toronto Island Canoe Club. After his three Olympic participations, he founded the Mississauga Canoe Club in 1957. Three of his sons, Dean, Reed, and Scott also competed at the Olympics in canoeing, and in 2001, his grandson, Mark, won two gold medals at the World Junior Canoe Championships in Brazil. During World War II Oldershaw worked as a tool machine designer, assembling anti-submarine devices. He later had a career in creative sales and promotion. He later began a hobby as an artist, designing artwork from flotsam he found washed up on a Lake Ontario beach. He also worked on restoring the Burlington Canal lighthouse and the lighthouse keeper’s cottage.