Watkins Glen International was added to the Truck Series schedule in 1996 as one of eight new tracks joining the calendar that season, and the only road course among them. The inaugural Parts America 150 on August 25, 1996 drew Cup Series drivers and team owners looking to gain additional road course familiarity: Joe Nemechek entered a truck for driver Steve Park, who set the fastest qualifying time, but Nemechek ultimately returned to the seat himself and started last. Ron Hornaday Jr. won the race, leading the final laps after passing Mike Skinner on lap 21.
The Watkins Glen truck race quickly became a showcase for road course specialists. Ron Fellows, a Canadian driver who had won at Watkins Glen in the Trans-Am Series in 1994 and 1995, dominated the event's early years. He won in 1997, claiming victory in just his third Truck Series start after passing points leader Jack Sprague with seven laps remaining and carefully conserving fuel. His 1997 win made him the first Canadian driver to win a race in the series.
Fellows returned to the pole in 1998 with a track-record lap time of 1:15.079, surpassing his own 1997 mark. The race that year produced an unusual result: Hornaday crossed the line first but received a two-second time penalty for jumping a restart, handing the win to runner-up Joe Ruttman.
In 1999, the event was renamed the Bully Hill Vineyards 150 and moved to June. The track was also repaved and reconfigured to the 2.4-mile NASCAR layout that season. Fellows once again overcame adversity, making a late pit stop to clear an oil-covered windshield before passing leader Mike Wallace with five laps to go for his third Watkins Glen truck victory.
Greg Biffle dominated the 2000 edition, leading the final 13 laps to win his third consecutive race and fourth in the last five events. Kurt Busch completed a Roush Racing 1–2 finish. It was the last truck race at Watkins Glen for more than two decades: the event was dropped from the 2001 schedule due to a scheduling conflict, as the only available date clashed with the Truck event at Kansas Speedway, leaving the series' 2001 calendar entirely composed of oval tracks.
Watkins Glen returned to the Truck Series schedule in 2021 as the 15th and final race before the playoffs. It was one of four road course events on that year's calendar, the most in series history. Track president Michael Printup attributed the return to scheduling flexibility created by the COVID-19 pandemic, which led other venues to cancel events and open date slots.
The 2021 race, sponsored by United Rentals, was shortened to 61 laps from the planned 72 due to lightning and scheduling concerns tied to the Xfinity Series race later in the day. Austin Hill was declared the winner as the race leader at the time of the stoppage.
Watkins Glen was again dropped from the schedule in 2022. The track was restored for 2025 as the second-to-last race of the regular season. Mission Foods assumed naming rights that year. For 2026, the race moved from August to May along with other Watkins Glen NASCAR weekends, and Bully Hill Vineyards returned as title sponsor, replacing Mission Foods.
The Watkins Glen truck race is notable as one of the rare occasions where road racing specialists have consistently out-performed oval regulars in a NASCAR touring series. Ron Fellows' three victories in four years established a high-water mark for road course ringers in Truck Series competition. The event's repeated removal and restoration reflects the tension between road course appeal and the logistical realities of aligning a truck schedule around the Cup Series calendar.