Charles Cromwell was born in Blenheim, Ontario. He was the son of Frank, an aerial trapeze artist, and Maud Cromwell. Frank and Maud worked for the Ringling Brothers Circus. Charles grew up and lived in Paris, Ontario but frequently traveled with his parents and the circus. Once Charles aged into a young adult he began working with the Yankee Robinson Circus as a rope walker.
A successful tight rope walk across the Niagara River gorge was completed by Charles Cromwell, although he failed to attract much media or public attention. Charles completed two crossings of the Niagara River Gorge. He utilized a 4.8 m long balancing pole that weighed 19 kilograms.