The "New York 500" initially was a second Watkins Glen round running for a shorter 500-kilometre (310 mi) distance compared to the Continental, using both classes of competitors.

However, in 1986, the race was split into two events, the prototypes retaining the 500 km event, and GT cars given a shorter 300 km (190 mi) race.

In 1987 prototypes were dropped entirely, and the race served as a 500 km GT event until 1991.

On April 7, 2021, IMSA announced the cancellation of the event at Canadian Tire Motorsport Park because of Canadian quarantine restrictions, replacing it with a standard-distance (three hour race, 2 hours, 40 minutes of racing format) at Watkins Glen International on Friday, July 2, dubbed the "WeatherTech 240 at The Glen."

The race used the format intended for Mosport, with all classes competing; however the GTD class only scored points towards the WeatherTech Sprint Cup.