The track's roots predate organised automobile racing at the site. In the early twentieth century, the oval at the Dundee Fairgrounds served harness racing, with trotters and pacers competing at agricultural fair events. The transition to stock car racing came in June 1957 when, in front of more than one thousand spectators, the Dundee Fairgrounds hosted its first stock car race. Glenn Reiners of Penn Yan took the victory in the 20-lap feature, inaugurating a motorsport tradition at the venue that has continued for nearly seven decades.
The non-profit Dundee Speedway Club took over management of the facility, leasing the track from the Dundee Fair Board and operating it for more than two decades. In 1983 Steve Wetmore was elected Club President and began a thirteen-year tenure as promoter, one of the longer continuous stewardships in the track's history.
During Wetmore's tenure, former track champion Lin Hough purchased the facility. After retiring from driving, Hough assumed the role of promoter and renamed the venue Black Rock Speedway. His family continued to run the track before eventually selling the property to Dean Hoag, the son of local racing legend Dutch Hoag. The Hoag family connection underlined the track's deep ties to regional racing heritage.
In 2016 Tyler Siri purchased the facility and renamed it Outlaw Speedway, the name under which it currently operates. The renaming reflected a fresh direction for the venue while maintaining the core weekly racing programme that had defined it across its previous incarnations.
On Friday evenings Outlaw Speedway runs a multi-class programme covering five divisions: Modified, IMCA Modifieds, Street Stocks, and Mini-stocks. The Modified class — featuring high-horsepower purpose-built dirt cars — sits at the top of the weekly competitive ladder and draws the strongest regional talent.
Outlaw Speedway occupies an advantageous geographic position near Watkins Glen International, one of North America's most celebrated road courses. Each year when Watkins Glen hosts a NASCAR Cup Series race weekend, Outlaw Speedway capitalises on the influx of visiting teams and media by staging a special event that attracts NASCAR Cup drivers for a night of dirt track racing. The contrast between the technical road course miles away and the raw dirt oval provides a distinctive experience for competitors and fans alike.
Beyond the NASCAR tie-in, the facility regularly hosts sprint car touring events from two of the sport's most prominent series: Tony Stewart's All Star Circuit of Champions and Kyle Larson's High Limit Racing. The presence of these national tours brings elite winged sprint car competitors to the Finger Lakes region and elevates the profile of events well beyond the local weekly programme.
Outlaw Speedway represents a type of small-market American dirt oval that serves as a cornerstone of grassroots motorsport. Its history — from harness racing through stock car competition under multiple names and owners — mirrors the trajectory of countless rural American short tracks that have adapted to changing economic and competitive landscapes over the decades. Its continued operation, weekly programme, and ability to attract major touring series demonstrate the enduring vitality of dirt track racing in upstate New York.