Old Dominion headlined Winstock 2019, bringing hits such as “Hotel Key,” “One Man Band,” and “Snapback” to the Winstock T-Mobile Stage.

Information Updated February 2021

Despite having to postpone the 2020 Winstock Country Music Festival due to the COVID-19 pandemic, its organizers are planning for the event’s return Friday, June 18 and Saturday, June 19, 2021, at the festival grounds southwest of Winsted.

More than 25 years ago, Winsted residents Tom Ollig and Dick Langenfeld had a bold idea for a fundraising initiative for Holy Trinity Catholic School.

In 1994, the first Winstock Country Music Festival took place at the Winsted Municipal Airport, with headliners Waylon Jennings, Crystal Gayle, and Winsted native Paulette Carlson, the former lead singer of the award-winning band Highway 101.

A few years after that first show at the airport, organizers moved Winstock to its permanent home across the street, allowing for a larger area for the event, expanded campgrounds, as well as the ability to improve grounds and infrastructure.

A permanent stage was built in 2007, and has since been graced by the likes of Luke Bryan, Jason Aldean, Miranda Lambert, the Oak Ridge Boys, Blake Shelton, Reba McEntire, and countless other country music stars.

Entertainment scheduled

With its planned return in 2021, one of country music’s hottest entertainers, Luke Combs, is set to take the stage Saturday, June 19 to close out the night.

Darius Rucker, lead singer of Hootie and the Blowfish, and bonafide country singer in his own right will headline Friday, June 18.

All artists who were scheduled to perform at the festival in 2020 have agreed to perform on the rescheduled dates in 2021.

Joining Combs and Rucker for main stage performances are Big & Rich with Cowboy Troy, Brett Eldredge, Chris Janson, Runaway June, Shenandoah, Phil Vassar, Eric Chesser, and Bobby Vandell & The Real Men of Country. Other national and regional acts will also perform throughout the weekend.

Tickets and more information

VIP tickets for 2021 sold out at the 2019 event. Reserved seating ($210), and general admission ($135) are available at, or by calling (320) 485-4287.

Camping passes ($130) and extra vehicle passes ($35) are also available.

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