Throughout its history, Winsted Municipal Airport has hosted airshows and the Winstock Country Music Festival.

Winsted Municipal Airport was dedicated on August 2, 1964, at an all-day event featuring a speech from U.S. Representative Ancher Nelsen, a United States Air Force flyover, and demonstrations of skydiving, cropdusters, radio-controlled aircraft, and helicopters.

[5] Due to the lack of agreement, the city council decided instead to repair the turf runway at a cost of $3.37 million.

[5] The United States Department of Transportation granted the project $1.44 million to relocate a pipeline running beneath the runway; other federal funds paid for a total of 90% of the project, with the state government covering 5% of the cost and the city covering the final 5%.

[8][9] In 1994, the annual Winstock Country Music Festival began to be hosted on the airport's grounds.