Wayne Webb built the track in 1946. Its length has been quoted at both a quarter mile and a fifth of a mile at different periods; the promotional description of "The World's fastest 1/5 mile dirt track" became the facility's signature claim. The buried bricks from the old factory occasionally rose to the surface, earning the track the nickname "The Other Brickyard" — a play on Indianapolis Motor Speedway's historical identity.
Under Webb Enterprises the track hosted a diverse programme of events beyond conventional oval racing, including USAC Midget and Sprint Car dates, figure-8 races, and novelty events such as Headlight Demo Derbies and Roundy-Round Demo Derbies. One of the signature events was the Herald & Review 100, a United Midwestern Promoters Late Model race with a $10,000 purse that attracted top names from across the Midwest and the broader United States, including Scott Bloomquist, Billy Moyer, and Ken Schrader.
In 1985, Bob Sargent and Track Enterprises took over Macon Speedway and aligned it with the UMP sanctioning body. The operation continued to attract high-calibre dirt talent. In 1994 the track transitioned to the NASCAR Winston Racing Series, drawing a different demographic of competitors and spectators. Track Enterprises sold the facility to a group of investors in 1998. Late Model racing was dropped from the programme in 1999.
In 2001, the Webb family returned to ownership when Rich Webb purchased the track. The facility closed its season early in 2006.
In 2007 the track was sold to a group comprising Bob Sargent, Ken Schrader, Kenny Wallace, and Tony Stewart. Under this ownership improvements were made to the facility and the track resumed competitive operations.
In 2022, Macon Speedway was sold again, this time to Chris Kearns, who was known as the promoter of the Wild West Shootout.
The facility's track records in major classes are: Winged Sprint Cars — 9.399 seconds, set by Chad Kemenah on 10 September 2004; Super Late Models — 10.228 seconds, set by Billy Moyer Sr. on 30 April 2015; Midgets — 10.325 seconds, set by Zach Daum on 1 July 2017.
Several drivers who raced regularly at Macon Speedway went on to national prominence. Jeff Leka won the 1999 NASCAR Winston Racing Series national championship. Justin Allgaier won the 2008 ARCA championship. Brandon Sheppard won the 2017 World of Outlaws Late Models championship. Jim Leka was among the regular competitors during the Webb era, and Gary Webb also competed at the facility.
Macon Speedway's continuous operation from 1946 into the 2020s places it among the oldest active dirt oval facilities in the American Midwest. Its combination of compact length, clay-and-sand composition, and a history of high-profile events has sustained its reputation as one of the faster short-track dirt ovals in Illinois. The track's alumni record across three different national championships — NASCAR, ARCA, and World of Outlaws — reflects the quality of competition it sustained throughout its history.