The track's history dates to 1914, when Frank Funk built a half-mile clay oval on a cornfield. The venue opened in 1916 under the name Funk's Speedway. From the outset, Funk pursued strategies to both boost attendance and improve racing conditions. He observed that attendance increased as the clay banking was raised higher and higher, reaching 25 feet by 1932 and reportedly reaching 45 degrees in the turns by 1948. The grandstands seated 6,000 by 1932, with the full grounds accommodating up to 14,000 spectators.
Funk also experimented with dust suppression treatments — starting with mineral oil and progressing to other substances — to create a surface described as "not only relatively dust-free but pavement fast." This work attracted the interest of highway engineers, who used the track as a proving ground for road-building technology.
The NASCAR Cup Series visited Winchester in 1950, with Lloyd Moore taking the victory. The track subsequently hosted the NASCAR Southeast Series for seven races between 1992 and 1998, the ASA National Tour for three events between 2000 and 2002, and the USAR Pro Cup Series for six races from 2001 to 2009.
USAC has maintained a long presence at Winchester, with midget, sprint, and USAC Silver Crown events held at the facility over many decades. The USAC Silver Crown race at the track has been titled the Rich Vogler Classic since 1991, honoring the late sprint car driver who died in a 1990 racing accident. A second Silver Crown round was also held at Winchester in 2005 and 2006 under the name Kenny Irwin Memorial, commemorating the NASCAR driver who perished in a 2000 practice crash at Indianapolis.
The ARCA Menards Series has raced the Winchester ARCA 200 at the track since 1982, with some interruptions. The venue joined the ARCA/CRA Super Series schedule from the series' inception in 1997 and has hosted it regularly ever since.
The track's signature event is the Winchester 400, an annual 400-lap super late model stock car race currently sanctioned by the ARCA/CRA Super Series. The race is one of the most prestigious short-track events in the Midwest. Over the first 36 editions, Bob Senneker proved the dominant force with seven victories. Mark Martin and Rusty Wallace — both of whom went on to distinguished NASCAR Cup careers — are among the multiple-time winners. Other past champions include Mike Cope (3 wins), Mike Eddy (2), Gary St. Amant (2), Ted Musgrave, Glenn Allen Jr., Tim Steele, Scot Walters, Butch Miller, and Hank Parker Jr.
Winchester has served as a proving ground and early-career stage for many drivers who reached the highest levels of American motorsport. Rusty Wallace, Mark Martin, Jeff Gordon, Tony Stewart, Ryan Newman, and Sarah Fisher are among the prominent names who have competed at the track. Chase Briscoe and William "Billy" Hutson are among more recent notable competitors.
Winchester Speedway's combination of extreme banking, high speeds, and tight confines makes it one of the most demanding and distinctive short tracks in North America. Its longevity — operating continuously since the mid-1910s — places it among the oldest active racing facilities in the United States. The steepness of its corners and the unique character of racing on the half-mile high-bank configuration continue to attract competitors and spectators from across the country, preserving its reputation as one of the genuine landmarks of American oval racing.