There had to be a first-ever champion of the first-ever 1966 Winnipeg-to-St. Paul International 500 cross-country race, and the future of sport could not have done better than the gregarious winner Herb Howe. Howe would pair his epic accomplishment and other racing victories with his penchant for great story telling to enjoy decades of notoriety while helping to grow the legend of the classic St. Paul Winter Carnival event.

A tall and robust racer as well as VP of Sales for Polaris distributor Larsen Olson, Howe captained a team of 21 racers who competed throughout the Midwest in ASA and USSA oval and cross-country. Howe won events in racing hotbeds like Munising, Antigo, Rhinelander, Houghton, Grand Rapids, Fergus Falls, Brainerd and at the World Series in Booneville, New York. He competed in the Winnipeg-to-St. Paul I-500 for 10 consecutive years, finishing seven of them to underscore his skill and tenacity in an era when fewer than 25 percent of the entrants would finish each event. He amassed 247 career podium finishes before retired from racing in 1976.

After hanging up his race bib he became Race Director for the I-500 and was responsible for routes, permits, timing, tech, fueling and surveillance until the Winter Carnival event ended in 1980. He reprised many of the same responsibilities again beginning in 1987 with the Jeep I-500 cross-country between Thunder Bay, Ontario, and White Bear Lake, Minnesota producing what is widely considered the most challenging of all I-500 cross country courses. When the final Thunder Bay I-500 ran in 1994, Howe ended his direct involvement with snowmobile competition. He currently lives in Siren, Wisconsin.