Prior to 1986, three races were held in 1957 (in one of the track's first professional races), as well in 1964 and 1965. These races were held in the track's original configuration, which was 2.35 miles long. The current NASCAR Cup race at the track began in 1986, utilizing a shortened 2.45 mile course. Following the 1991 death of
J. D. McDuffie in a crash in the Outer Loop, at the end of the backstretch, and a subsequent, serious crash by
IMSA driver,
Tommy Kendall, the Inner Loop "bus stop"
chicane was added just before the Outer Loop. NASCAR has since utilized this "short course," and has never utilized the "Boot" as
IndyCar and
Formula One have. Some drivers, however, have proposed the use of the full course. During a 2011 Mobil Oil "Car Swap" at Watkins Glen using the course,
Tony Stewart pushed for using the Grand Prix course after driving demonstration laps in both his
Chevrolet Impala and the majority of his laps in a
McLaren MP4-23 as part of the event with
Lewis Hamilton.
ESPN broadcast the race from 1986 to 2000, then again in 2007 to 2014. Starting in 2015 (current contract),
NBC had the rights to broadcast the race but the 2015 edition was aired on
NBCSN. In 2016, the race was put on
USA Network because of the
2016 Summer Olympics airing on NBC and NBCSN. Beginning in 2017, with the exception of 2025, NBC decided to broadcast this race in the style of radio where various analysts would be placed on the course to report what they see in their section of the track to the viewer. In
2020, the race was not held due to the
COVID-19 pandemic. The State of New York was requiring travelers from several states to isolate for 14 days (including North Carolina, where most of NASCAR's teams are located, and Florida, where NASCAR's corporate offices are), and not giving the series a quarantine waiver to enter the state. NASCAR instead held a race on the
Daytona International Speedway road course, the
Go Bowling 235. 2024's running of this race was moved to September was the second race of the Round of 16 in the
NASCAR playoffs. Watkins Glen's stint in the playoffs was short-lived however, as in the 2025 season, Watkins Glen returned to its typical August date. In 2026 the race was moved to a mid-May date. On December 3, 2025, NASCAR released a schedule for the race weekend that included an extension of the race to 100 laps. ==Past winners==