Notable drivers that raced at Winchester include Rusty Wallace, Mark Martin, Jeff Gordon, Tony Stewart, Ryan Newman, Sarah Fisher, Chase Briscoe and William "Billy" Hutson.

He started with mineral oil, then branched out into various other substances, which would result in a track "not only relatively dust free but pavement fast.

"[4] This work brought the attention of highway engineers, who made the track a proving ground for roadbuilding technology.

Former winners during the first 36 editions include: Bob Senneker (7 wins), Mike Cope (3), Mike Eddy (2), Mark Martin (2), Gary St. Amant (2), Butch Miller, Rusty Wallace, Ted Musgrave, Glenn Allen Jr., Tim Steele, Scot Walters, and Hank Parker Jr.

The venue regularly hosts additional ARCA/CRA Super Series races every year since its inception in 1997.