The Winstock Country Music Festival in Winsted, Minnesota, is turning up the heat for summer 2026 with a lineup that promises to draw fans from across the state and beyond. Headlined by Luke Bryan and Dierks Bentley, this year’s festival features a slew of rising and established country stars.
Bryan, a country powerhouse with 26 No. 1 hits and multiple CMA Entertainer of the Year honors, brings star power and stage presence. Bentley adds his own flair, mixing hits, storytelling, and the energy fans expect. Alongside them will be Carly Pearce, known for her expressive vocals and emotional songs; Mitchell Tenpenny, who’s steadily carving his niche; Easton Corbin, offering that traditional country vibe; plus the emerging duo Maddie & Tae.
The festival spans June 19-20, 2026. Beyond the headliners, the supporting acts help round out what looks to be a thoughtful contrast between mainstream appeal and honky-tonk roots. Winstock, which doubles as a fundraiser for local schools, is making sure it preserves its community heart even as it draws a bigger country crowd. For country fans in the Upper Midwest, this lineup underscores just how vibrant the genre remains—able to unite legends, breakout artists, and longtime traditionalists under one big tent.
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