Musgrave's father, Elmer, was a famous short-track racer in the Midwest who raced for over 25 years at Soldier Field, O'Hare, Waukegan, and Wilmot, Wisconsin before moving into asphalt late models in the American Speed Association (ASA) and ARCA. "I was really young at the time," Musgrave said. "But I can still remember sitting in the infield at Milwaukee and watching him race against drivers like Paul Goldsmith. He finally retired so he could help my older brother, Tom, and I get started." He began racing in 1977 at age 22 at Waukegan in a 1967 Ford Galaxy that he inherited from his brother. He immediately rebuilt the car into a 1967 Ford Torino and won the track's rookie of the year award.. He and his father built a Ford Mustang using some tips from Dick Trickle to race the next season.

By 1979 he was a regular driver on the Central Wisconsin (CWRA) circuit, finishing seventh in the season points. Originally from Illinois, Musgrave moved across the nearby state line so that he could race five nights per week in the CWRA. He raced at LaCrosse, State Park Speedway in Wausau, Grundy County Speedway, Wisconsin Dells Speedway (now Dells Raceway Park), and Waukegan. In 1981, he finished third in the points at Wisconsin International Raceway (WIR), two points behind Alan Kulwicki. Musgrave's highlight of the 1982 season was winning the Holiday 50 at Capital Speedway (now Madison International Speedway). Musgrave qualified the fastest five times in a row at WIR and was leading the points when he battered his wrist in a wreck. He returned the following week in a cast with a special arm support in the car. He finished third in points. Musgrave won ten CWRA features in 1983, including the Holiday 50 at Capital Super Speedway, the Triple Hot Dog Dash at Wisconsin Dells, and the Race of Champions at Capital's Oktober Nationals. Musgrave won seven features at Capital in 1984, along with two features at LaCrosse, two at State Park, and two at Wisconsin Dells. He ran out of money to fund his team in 1985, and he ended his season early. Musgrave returned in 1986 with a new car which contained several of his experimental ideas. He finished tenth in CWRA points even though he started the season over a month late. He had numerous feature wins that season, including the Firecracker 100 at Capital.

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