It is often considered to be the first major country music festival of the summer in the upper Midwest.
[1] The Winstock Country Music Festival was started in 1994 by a group of Holy Trinity School and Parish boosters.
The first Winstock was held at the Winsted Municipal Airport and one of the headliners was local country star Paulette Carlson.
Since then, Winstock has grown and moved across the road to land the festival now owns.
Notable performers at Winstock have included Alabama, Tim McGraw, Montgomery Gentry, Reba McEntire, Brad Paisley, Brett Eldredge, Brooks and Dunn, Martina McBride, Lee Brice, Gary Allan, Miranda Lambert, Luke Combs, Alan Jackson, Waylon Jennings, Toby Keith, Willie Nelson, Jake Owen, and Blake Shelton.