Stock car racing at Watkins Glen stretches back further than the modern era. Three early races were staged in 1957, 1964, and 1965 on the track's original 2.35-mile configuration, but the current annual event traces its roots to 1986, when NASCAR began running a shortened 2.45-mile course at the circuit.
The layout was altered significantly following the death of J.D. McDuffie during the 1991 race. McDuffie lost his life in a crash at the Outer Loop at the end of the backstretch, and a subsequent serious accident involving IMSA driver Tommy Kendall at the same section prompted the addition of an Inner Loop "bus stop" chicane just before the Outer Loop. NASCAR has used this modified 2.45-mile short course ever since and has not adopted the full Grand Prix course that IndyCar and Formula One have utilized. Some competitors have advocated for using the longer layout, including Tony Stewart, who pushed for the full course during a 2011 Mobil Oil Car Swap event at the circuit in which he also drove demonstration laps in a McLaren MP4-23 alongside Lewis Hamilton.
ESPN held the television rights to the race from 1986 to 2000, and again from 2007 to 2014. NBC gained the broadcast rights starting with the 2015 season as part of a major contract restructuring. The 2015 edition aired on NBCSN rather than the main NBC network; in 2016, the race moved to USA Network because scheduling conflicts with the Summer Olympics occupied both NBC and NBCSN. Beginning in 2017, NBC adopted an approach modeled on radio-style coverage for the race, placing analysts at various points around the course to report on what they observed in their respective sections.
The 2020 edition of the race was cancelled due to the COVID-19 pandemic. New York State required travelers from several states — including North Carolina, home to the majority of NASCAR's teams, and Florida, where NASCAR's corporate offices are located — to quarantine for 14 days upon arrival. NASCAR did not receive a quarantine waiver, making it logistically impossible to hold the event. As a substitute, NASCAR organized the Go Bowling 235 on the Daytona International Speedway road course that year.
For the 2024 season, the race was shifted to September and became the second event of the Round of 16 in the NASCAR playoffs, marking Watkins Glen's first inclusion in the postseason bracket. The track's stint in the playoffs proved short-lived; for the 2025 season, the race returned to its customary August date. In 2026, the event was moved again to a mid-May slot. That same year, NASCAR confirmed Watkins Glen would return to the playoff schedule in 2027.
The race at Watkins Glen occupies a unique place in the Cup Series calendar as one of the longest-running road-course events in the sport's modern era. The circuit's challenging layout, featuring a mix of fast sweepers, elevation changes, and the technical bus-stop section added in the early 1990s, consistently produces racing that differs markedly from NASCAR's oval-track events. The ability of road-course specialists and open-wheel crossover drivers to compete strongly at the Glen has made it a recurring talking point about the diversity of skills required across the full Cup Series season.