Former governor of New York Andrew M. Cuomo awarded fourteen projects in hopes that they would be catalysts for increased private investment in the village.

This grant was largely secured by the work of local government officials and the Schuyler County Partnership for Economic Development (SCOPED).

After his brother's death, Samuel Watkins inherited the property and spent four decades building up the area with roads, shops, and a hotel.

The first Watkins Glen Sports Car Grand Prix was held in 1948 on public streets in and near the village.

During the 1952 race, driver Fred Wacker struck onlookers sitting on a curb on a corner coming down West 4th St. (State Route 409), killing a 7-year-old boy and injuring 10 others.

It has hosted nearly every type of road racing, from the Sahlen's 6 Hours of Watkins Glen (1948-current), the Formula One United States Grand Prix (1961–1980), and the I Love New York 355 at The Glen (1957-current), which was one of the few races on the Monster Energy NASCAR Cup Series schedule not conducted on an oval speedway, the other being Sonoma Raceway until NASCAR added more road courses to the Cup Series schedule.

The International Motor Racing Research Center, a professional archive of motorsports history, opened in June 1999 in an annex of the Watkins Glen Public Library.

The event has always been free to spectators and features both closed course racing and freestyle competition using standup, sit-down, and sport class machines.

On July 1–3 of 2011, the band Phish hosted Superball IX, a three-day music festival on the same grounds as the Summer Jam of '73.

Phish planned to return to Watkins Glen for their 11th festival, Curveball, on August 17–19, 2018 but was forced to cancel when their permit was revoked due to floods contaminating the local water supply.

[15] Watkins Glen is the home port for True Love, a schooner built in 1926 that was featured in High Society (1956).