Bigelow began his racing career at the Badger Midget Racing Association, competing at Angell Park Speedway in Sun Prairie, Wisconsin. His first attempt at the National Championship came in 1967, when he finished eighteenth. He collected midget wins in 1968 at Hales Corners Speedway in Hales Corners, Wisconsin, and at the Sycamore, Illinois, circuit, and won the inaugural Astro Grand Prix held inside the Houston Astrodome in 1969.
Bigelow made his USAC Championship Car debut in 1968 and went on to accumulate 104 combined starts across the USAC and CART series over a career spanning 1968 to 1983 and a return in 1985. He finished in the top ten on 39 occasions and his best results — two second-place finishes — came in 1978 at Texas World Speedway and at Milwaukee.
His Indianapolis 500 record stands as one of his defining achievements. Bigelow qualified for and started the race every year from 1974 through 1982, a run of nine consecutive starts. His best finish at Indianapolis was sixth place in 1977.
Bigelow established himself as a formidable sprint car competitor, becoming USAC Sprint Car Series Champion in 1978. During his sprint car career he set the record for most wins in a single season with fourteen and accumulated 52 USAC Sprint Car victories in total — a figure that reflected both his consistency and longevity at the top level of American short-track racing.
After a successful spell in championship cars, Bigelow returned to his midget car roots. He won back-to-back USAC Speedrome championships in 1982 and 1983, then claimed the 1984 USAC National Midget Series Championship — a title he won driving the number 16 car owned by Carl Sandy. He also won the 1982 USAC Midwest Regional midget car title. In the seasons following his 1984 national title, he finished fourth, third, and ninth respectively. Bigelow also resumed competitive midget racing from 1981 onward, driving for Sandy Racing.
Bigelow made a single NASCAR Winston Cup Series start, entering the 1986 Atlanta Journal 500 at Atlanta International Raceway. He finished fortieth after suffering engine problems.
Bigelow was inducted into the National Sprint Car Hall of Fame in 1996 in recognition of his exceptional career in American sprint car racing. In 2002 he was inducted into the National Midget Auto Racing Hall of Fame, with his home track at Angell Park Speedway in Sun Prairie serving as the venue for that honour.
Following his retirement from competition, Bigelow moved into broadcasting. From 2009 he served as a colour commentator for Fox Sports Network covering Must See Racing Xtreme Sprint Series television broadcasts.
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