 Cummings is the only runner to finish second in San Francisco's Bay to Breakers 12K road race (Guinness World Record largest road race) three years in a row (1984, 1985, and 1986).On March 15, 1987, Cummings broke the American Record in the 20K, at New Bedford, Massachusetts, in a time of 59.13.Cummings continued running into his 40s.