Con Olson was born in Sydney, Nova Scotia. During his twelve-year running career, he represented Cape Breton in every kind of running event from three miles to the standard twenty-six-mile marathon.

Olson began racing in 1926 and established many big wins and records. He was the Cape Breton Champion for six consecutive years (1930 to 1936) in the three-mile distance and four consecutive years (1932 to 1937) in the five-mile distance. His five-mile race time was 25.17.

In the longer races, he won the Cape Breton Ten-Mile Championship four times, and was the winner of the Cape Breton Marathon three out of the four times he entered it. Con competed in the Halifax Modified Marathon, placing first in 1936 and second in 1937. He also ran in the Boston Marathon twice, with a 19th-place finish in the 1931 Marathon, and a 36th-place showing in the 1936 Marathon.

He ran 208 races in total, winning 189 of them. The day after the official opening of the Canso Causeway, Con ran across the causeway from Cape Breton to mainland Nova Scotia.