In 1940, Redington enlisted in the United States Army, and joined the 6th Field Artillery Regiment at Fort Hoyle, Maryland.
On February 18, 1953, he married Violet Redington, and they moved to a new homestead on Flat Horn Lake, Alaska and worked from 1954 to 1958 as hunting guides along the Iditarod trail.
She wanted to sponsor a sled dog race to commemorate the 100th anniversary of the purchase of Alaska from Russia, but had been unable to get the support of an experienced musher.
In February 1967, 58 dog mushers competed in two heats along a 25-mile (40 km) stretch of the old Iditarod Trail between Wasilla and Knik.
Redington wanted to expand the race, from Knik to the historic gold rush town of Iditarod, but changed the end-point to the more-recognizable Nome, more than 1,000 miles (1,600 km) away.
In 1973, Dick Wilmarth of Red Devil, Alaska, and his lead sled dog Hotfoot beat a pack of 34 mushers who competed in the race to Nome.
Negative publicity caused by the death of several dogs during the race reduced the purse to only $31,000 in 1974, but the event still attracted a field of 44 mushers.
In 1975, the race instituted stronger dog care requirements, and a corporate sponsor raised the purse back to $50,000.