Under the vast blue skies of McLeod County, where the cornfields sway like a slow-dancing crowd at a backroad bar, the Winstock Country Music Festival has long been more than just a gathering of guitars and good times. It’s a heartbeat—a two-day pulse of pedal steel, heartfelt ballads, and the kind of communal joy that turns strangers into lifelong friends. Founded in 1994 as a humble fundraiser for the local Holy Trinity School and Parish, Winstock has grown from a modest airport runway affair into one of the Upper Midwest’s crown jewels of country music, drawing 12,000 to 15,000 fans each day across its sprawling grounds. And on this crisp autumn morning, as goldenrod blooms along Highway 7, the festival’s organizers dropped a bombshell that has the heartland humming: the full lineup for Winstock 2026, headlined by none other than country superstars Luke Bryan and Dierks Bentley.
The announcement, made via a star-spangled social media blitz and a packed press conference at the Winsted American Legion, lit up timelines from the Twin Cities to Tulsa. “We’re thrilled to bring this powerhouse duo to our stage,” said Winstock board president Tom Schaefer, his voice gravelly with the pride of a man who’s volunteered thousands of hours to keep this volunteer-run nonprofit thriving. “Luke and Dierks aren’t just headliners; they’re the soul of what country means—stories of love, loss, trucks, and triumphs, sung with a boot-stompin’ authenticity that resonates from the stage to the back forty.” Set for June 19 and 20, 2026, the 32nd edition of Winstock promises an expanded roster of acts, earlier start times for more daylight twang, and camping options that sold out faster than a last-call round. Tickets went on sale Wednesday morning, with general admission priced at $155 for the weekend—a steal for two days of sun-soaked anthems and the kind of memories that outlast a hangover.
At the top of the bill, Dierks Bentley takes the Friday night slot, bringing his whiskey-soaked baritone and a catalog of hits that have defined a generation of tailgate parties. Known for blending bluegrass roots with modern country edge, Bentley’s performance will cap a day stacked with rising talents like Easton Corbin and Mitchell Tenpenny. Then, on Saturday, Luke Bryan storms the stage, fresh off another season judging American Idol and riding high on his fifth Entertainer of the Year nod from the ACM Awards. Bryan’s set, expected to run deep into the twilight, will feature crowd-pleasers like “Country Girl (Shake It for Me)” and “Huntin’, Fishin’ and Lovin’ Every Day,” flanked by openers Carly Pearce and Lauren Watkins. “Winstock has always been about family and community,” Bryan said in a pre-recorded video message played at the reveal. “I’m honored to join this Minnesota tradition and crank up the volume on what makes country the soundtrack of our lives.”
But the lineup doesn’t stop at the headliners—far from it. Organizers unveiled a diverse slate that spans classic twang to fresh-faced firebrands, ensuring every fan finds their jam. Friday’s undercard kicks off with opener Jake Nelson, the Minnesota native whose heartfelt takes on small-town life have earned him a devoted regional following. He’ll hand off to Roseland, a high-energy Americana outfit blending fiddle and banjo with rock-infused grit, before the evening escalates with Lauren Watkins’ soulful storytelling. Watkins, whose breakout single “Bad With Boys” climbed charts last year, brings a raw vulnerability that’s already drawing comparisons to Kacey Musgraves. “Winstock feels like home,” Watkins shared on Instagram post-announcement. “Can’t wait to share these songs under those big skies.”
Saturday ramps up the star power early, with Mitch Gordon Band delivering a noon-hour set of foot-stompin’ originals that nod to the festival’s Midwestern ethos. AUSTIN G follows with his genre-bending fusion of hip-hop beats and country hooks, a nod to the evolving sound of Nashville’s next wave. By mid-afternoon, Carly Pearce takes the West Stage, her powerhouse vocals belting out empowerment anthems like “Never Wanted to Be That Girl.” Pearce, a Grammy winner with a knack for blending heartbreak with hope, has been vocal about her love for intimate festivals like Winstock. “It’s not about the spectacle; it’s about the connection,” she told Billboard last month. Rounding out the day before Bryan’s grand finale is Scotty McCreery, the American Idol alum whose baritone barroom ballads, including the platinum “Five More Minutes,” have solidified him as a festival staple.
This year’s reveal comes on the heels of a blockbuster 2025 edition, where Thomas Rhett and Jordan Davis packed the grounds with over 30,000 attendees across the weekend. Rhett’s Saturday closer, a rain-soaked singalong of “Die a Happy Man,” became the stuff of legend, while Davis’s Friday fireworks display synced perfectly to “Buy Dirt.” But Winstock’s magic isn’t just in the music—it’s in the marrow of the community. Every ticket sold funnels proceeds back to private education scholarships for Winsted-area students, a mission that’s awarded over $2 million since inception. More than 1,000 volunteers log 5,000-plus hours annually, from slinging burgers at the food tents to wrangling RVs in the campgrounds. “This isn’t a business; it’s a family affair,” Schaefer emphasized. “Luke and Dierks get that—they’re the kind of artists who show up early, sign autographs late, and treat our volunteers like kin.”
To understand Winstock’s enduring appeal, you have to rewind to those scrappy beginnings. In 1994, a cadre of Holy Trinity boosters, led by figures like Schaefer’s late father, dreamed up a one-off event to bolster the parish’s dwindling coffers. Held on the dusty tarmac of Winsted Municipal Airport, the inaugural fest drew a few hundred locals with headliner Paulette Carlson, the former Highway 101 frontwoman whose “Jimmy Makes Me Tremble” still echoes in karaoke bars. “We had more mosquitoes than people that first year,” recalls original organizer Mary Beth Olson, now a board emerita. “But the music? It lit a fire. Folks danced till dawn, and by Sunday, we knew we’d struck gold.”
By 1995, Winstock crossed the road to its current 160-acre site, a former cornfield transformed into a festival village complete with two stages, shaded beer gardens, and campgrounds that stretch like a tent city suburb. The addition of the West Stage in 2005 birthed the Emerging Artist series, a launchpad for stars like Little Big Town and Sugarland. Over three decades, the lineup reads like a who’s-who of country royalty: Alabama’s harmonious harmonies in ’98, Tim McGraw’s electric charisma in 2002, Reba McEntire’s timeless glamour in 2010, and more recent thunder from Miranda Lambert, Luke Combs, and Toby Keith. “We’ve hosted legends who became family,” says volunteer coordinator Lisa Hartmann. “Waylon Jennings once crashed a volunteer potluck—ate three helpings of hotdish and called it ‘the best damn casserole tour.'”
That legacy of accessibility sets Winstock apart in a festival landscape dominated by mega-events like Stagecoach or Bonnaroo. Here, the VIP pit rubs elbows with the GA faithful, and artists often mingle post-set in the beer tent. It’s a throwback to country’s communal roots, amplified by modern perks: solar-powered stages, farm-to-table food trucks slinging walleye tacos and brisket sliders, and kid zones with pony rides and cornhole tournaments. The annual Beanbag Tournament, a cornhole showdown with cash prizes, has become as iconic as the music, drawing competitive souls from across the Dakotas. And let’s not forget the Rumble on the Road, a mini-demolition derby that kicks off Saturday with engines roaring louder than the amps.
As for the 2026 headliners, their pedigrees couldn’t be more tailor-made for Winstock’s vibe. Dierks Bentley, 50, exploded onto the scene in 2003 with “What Was I Thinkin’,” a cheeky tale of reckless romance that topped charts and captured his everyman charm. Over eight albums, he’s evolved from bro-country provocateur to roots revivalist, earning nine Grammy nods and a shelf of gold records. His 2025 release, Back Porch Revival, leaned heavy on bluegrass collaborations with Alison Krauss, but fans know he’ll dust off the hits at Winstock—expect a raucous “Drunk on a Plane” singalong as the sun dips low. Bentley’s no stranger to the fest; he guested in 2012, charming the crowd with an impromptu “Sweet & Wild” cover. “Winstock’s got that pure, unfiltered energy,” Bentley posted on X. “Like a family reunion with better whiskey. See y’all in ’26.”
Luke Bryan, 49, is the festival’s Saturday savior—a Georgia farm boy turned global icon whose easy grin and everyman lyrics have sold 75 million records worldwide. From “That’s My Kind of Trouble” in 2011 to his 2024 duets album with Brooks & Dunn, Bryan’s career is a masterclass in relatability. He’s the guy who’ll croon about dirt roads one minute and mentor dreamers on Idol the next, all while packing arenas with a party-hearty ethos. Winstock marks his return to the Midwest circuit post his 2023 Farm Tour, where he played for farmers and families in similar small-town outposts. “Minnesota’s got that heartland soul I grew up on,” Bryan enthused. “Can’t wait to raise hell with 15,000 of my closest friends.”
The supporting cast adds layers of intrigue. Easton Corbin, with his beachy baritone and “A Little More Country Money” swagger, slots in Friday afternoon for a set that’s equal parts nostalgic and nostalgic. Mitchell Tenpenny, the Tennessee tunesmith behind “Drunk Me,” brings pop-country polish, while Lauren Watkins—fresh off a CMA New Artist push—infuses raw emotion drawn from her Louisiana upbringing. Carly Pearce’s Saturday slot is a powerhouse showcase; the Kentucky native’s journey from Opry opener to “Hide the Wine” hitmaker embodies resilience, especially after her public battles with heartbreak and health. Scotty McCreery rounds out the heavy hitters, his deep-dish voice perfect for Winstock’s sunset ballads.
Fans wasted no time snapping up passes. By noon on sale day, campgrounds A through D—prime spots with fire rings and communal showers—were history, thanks to pre-renewals at 2025’s fest. Reserved seating, offering shaded bleachers and closer views, dwindles fast, but GA tickets remain plentiful. “It’s selling like last year’s limited-edition koozies,” jokes ticket manager Sarah Kline. Packages start at $155 for GA weekend access, climbing to $450 for VIP with express lanes and artist lounge perks. Camping add-ons run $100-$200, including Thursday pre-party access featuring The Johnny Holm Band’s polka-infused country romp.
What elevates Winstock beyond the playlist is the tapestry of experiences woven around it. Picture this: dawn breaking over dew-kissed tents, the sizzle of bacon from food vendors like Holy Trinity’s famous Jell-O salad stand, and the low hum of guitars tuning on the West Stage. By midday, the air thickens with funnel cake and craft brews from local legends like Badger Hill Brewing. Families picnic on quilts, kids chase each other through the Beanbag Village, and couples two-step in the sawdust dance area. As evening falls, the Main Stage ignites—LED lights cutting through twilight haze, bass thumping like a heartbeat. Post-headliner, the after-parties rage in the beer tent, where cover bands riff on Bentley and Bryan till the wee hours.
Sustainability is another Winstock hallmark. In 2024, they piloted a zero-waste initiative, diverting 80% of trash through composting and recycling stations manned by green-thumbed volunteers. Solar panels power the stages, and shuttle services from Winsted’s hotels cut down on parking chaos. “We’re stewards of this land,” Schaefer says. “The same fields that grew corn now grow memories—and we’ll leave ’em better than we found ’em.”
Of course, no festival is without its folklore. Winstock alums swap tales of the 2010 monsoon that turned grounds to gumbo but didn’t dampen Reba’s set; the 2018 solar eclipse viewing party synced to Alan Jackson’s “Chattahoochee”; or the time Blake Shelton judged an impromptu pie-eating contest, crowning a grandma from Eau Claire. These moments, captured in the festival’s Poster History archive—a gallery of 32 vibrant designs—remind attendees why they return year after year.
As 2026 looms, the buzz is electric. Social media swirls with fan art of Bryan in flannel and Bentley in a lumberjack hat, while local radio stations like 93.7 The Wolf tease countdowns. Regional acts like Jake Nelson, a Winsted-raised troubadour, add hometown flavor, bridging the gap between national stars and the folks who built the fest. “It’s our Super Bowl,” Nelson grins. “And this lineup? It’s overtime.”
In a world of fleeting trends, Winstock endures as a testament to country’s core: unpretentious, unbreakable, and utterly alive. As Schaefer wrapped the presser, he raised a toast with a plastic cup of Leinenkugel’s. “To Luke, Dierks, and everyone in between—see you under the Minnesota stars. Let’s make 2026 the one they sing about for years.”
For tickets, schedules, and camping deets, hit winstockfestival.com or dial (320) 485-4287. Gates open Thursday, June 18, for early birds; music fires up Friday at 4 p.m. Pack your boots, your buddies, and your best stories—Winstock’s calling.
