Plans for the stadium were filed in November 1936 by Winston-Salem mayor W. T. Wilson with the Works Progress Administration during the Great Depression, supported by a $35,000 investment from Nathalie Gray Bernard, widow of Bowman Gray Sr., a former president of the R. J. Reynolds Tobacco Company. The facility was named in his honor. Construction began in February 1937 and was completed in March 1938 at a final cost of approximately $200,000, twice the original budget. The stadium officially opened on May 1, 1938, hosting a Christian music festival, with its first college football game following in October of that year.
Auto racing first appeared at the facility on September 1, 1939, when promoter J. C. Calhoun organized a midget car program on a dirt track that surrounded the football field. A second attempt at regular racing under promoter Lou Franco in 1947 resulted in the paving of the dirt oval, but Franco's operation was plagued by poor attendance, safety failures, and at least one driver fatality, and ultimately collapsed when Franco abandoned the city with unpaid debts.
In 1949, racing promoters Bill France Sr. and Alvin Hawkins assumed the stadium's racing lease and brought the facility under the newly formed NASCAR sanctioning body. France Sr. was initially hesitant but was persuaded by Hawkins, and the partnership also agreed to assume Franco's paving debts as part of the arrangement. Their programs proved immediately popular, and by their fourth year the stadium had climbed out of financial debt and was generating consistent profits. Attendance growth during this period funded a series of improvements, including expansions to the scoreboard, lighting, and in 1954, a capacity increase to 17,970 seats.
Bowman Gray hosted its first NASCAR Cup Series race on May 24, 1958, with Bob Welborn winning the event. The stadium ran Cup Series points-paying races until 1971, when the final such event ended controversially: winner Bobby Allison was disqualified for running a smaller Grand American car in a race that nominally permitted both Grand American and Grand National machinery. The disqualification stood for over five decades before NASCAR reversed it in 2024 and awarded the victory to Allison.
Following the end of Cup Series visits in 1971, the stadium continued hosting lower-series NASCAR Weekly Series racing across modified, sportsman, street stock, and stadium stock divisions. The weekly races developed a reputation for intensity and driver confrontations, with fights among competitors becoming a noted feature of the culture.
Through the late 1970s and 1980s the stadium's condition declined steadily. Winston-Salem State University (WSSU) made multiple attempts to purchase the facility, offering $125,000 in 1979 and $450,000 in 1980, but both efforts stalled without city council approval. A 1997 city proposal to invest $1.15 million in bonds for renovation was also rejected by a public vote.
In November 2018, the city of Winston-Salem announced a $9 million renovation project covering the resurfacing of the racing oval and additional stadium improvements, keeping the facility under city ownership after WSSU withdrew from purchase negotiations. Construction began in November 2020, with the track repave and football field regrading completed in 2021 and the full project finished in April 2022. An unusual second repave of the track surface was required later the same year after the new surface showed atypical deterioration during the 2022 season.
In March 2024, NASCAR took over the racing operations lease from the Hawkins family-owned Winston-Salem Speedway, Inc., ending a 75-year association between the Hawkins family and the stadium. Five months later, NASCAR announced that the annual Clash exhibition race — previously held at the Los Angeles Memorial Coliseum — would move to Bowman Gray Stadium beginning in 2025. The return marked the first Cup Series event at the facility since 1971.
Preparations for the 2025 Clash included the installation of a new lighting system and the replacement of surrounding guardrails with SAFER barriers and protective catch fencing. The race took place on February 2, 2025. In June 2025, the Winston-Salem City Council approved funding for a new $1,000,000 digital LED video scoreboard, contingent on NASCAR continuing to host one of its top three series at the facility over the following five years.
Bowman Gray Stadium holds an unusual place in American motorsport as a venue where professional football, college athletics, and top-level stock car racing have coexisted on the same footprint for nearly nine decades. Its history with NASCAR predates the sanctioning body's rise to national prominence, and its weekly racing program has functioned as a proving ground for generations of short-track drivers in the Southeastern United States. The stadium's capacity of approximately 17,000, combined with its flat quarter-mile oval, creates racing conditions unlike any other venue on the NASCAR calendar.