PENDLETON â Pendleton Whisky Music Fest is ready to thrill again. Songwriters Hall of Fame inductee and two-time Academy of Country Music Awards Entertainer of the Year Toby Keith is set to headline the annual summer event July 10, 2021, at the historic Pendleton Round-Up Grounds. Country musicâs Clare Dunn, Clay Walker and Cole Swindell also are slated to perform, according to the announcement from Pendleton Whisky Music Fest. Organizers canceled the 2020 festival due to the coronavirus pandemic. The new lineup of 2021 performers will replace the original headlining artist Eric Church, who is now set to perform at the Pendleton Whisky Music Fest in 2022, along with Macklemore.