Three Days at Boots and Hearts 2026
Boots and Hearts turned 15 this year, and it celebrated the milestone by doing something it had never done before: handing the Friday night headline slot to a pop-rock band. Over three days at Burl’s Creek Event Grounds in Oro-Medonte, the bill ran from a Canada’s own Brett Kissel, to Kevin, Joe, and Nick Jonas closing it out and the festival’s willingness to stretch its own definition of “country” made for one of the more interesting lineups Boots and Hearts has put together.

The Emerging Artist Showcase: Leah Holtom Takes the Crown

Every Boots and Hearts weekend starts the same way: with the artists on the verge of making their breakthrough. The Emerging Artist Showcase has been a launching pad for Canadian country talent since 2012, with alumni like Josh Ross, Owen Riegling, and The Reklaws all having come through its ranks, and this year’s crop of eight finalists, Landon Bedor, Connor Eller, Leah Holtom, Taylor Jensen, Laila, The Mainlanders, Jackson Klippenstein, and YASSiN & Sean Terrio, was picked from a nationwide field.

Leah Holtom, a singer-songwriter from Brampton, Ontario, took the title, earning the showcase’s grand prize: a $10,000 cash award, a single release through Universal Music Canada, artist development sessions with RLive Management, a Gibson J-45 guitar and VIP trip to the Gibson Garage in Nashville, and a guaranteed slot on the 2027 Boots and Hearts bill.

Friday: Redefining a Country Music Headliner

Once the showcase wrapped, Friday’s card kept climbing. School House, last year’s Emerging Artist Showcase winners, played an early tent set that doubled as a nice piece of festival continuity, a reminder of what a showcase win can turn into twelve months later. The group leaned into each other mid-riff, all matching earthy-toned outfits and genuine grins, the kind of loose, unchoreographed chemistry that only shows up once a band has actually logged real stage time together.

Dasha, backlit against a clear afternoon sky in a metallic mesh top, mic in one hand, arms thrown wide, hair catching the wind on nearly every chorus, was the first to take the main stage. It was a performance built for spectacle, and the crowd around the rail thickened visibly between her first song and her last.

Emily Ann Roberts hit the Front Porch Stage in a ruffled pink dress, at one point swinging a hand-painted acoustic overhead mid-song, an unscripted, joyful moment that summed up her set well.

Brett Kissel kept the homegrown-Canadian thread running and brought the most physical energy of the day’s tent sets, leaping mid-air with his acoustic strapped on, hat staying perfectly in place, fiddle player and full band filling out the stage behind him through a haze of backlit smoke.

By the time Russell Dickerson took the main stage as the sun started to drop, the production had scaled up to match the evening slot: smoke jets framing him on both sides of the stage, a massive LED screen behind reading “RUSSLEMANIA,” and a crowd already thick with raised phones and cowboy hats.

Then came the Jonas Brothers, marking their first-ever country festival booking and the clearest sign yet of how far Boots and Hearts was willing to push the definition of “country” for the festival’s 15th anniversary. The walk-out alone was a highlight: Kevin, Joe, and Nick emerging as three backlit silhouettes inside a single spotlight before a note played, all denim and sunglasses, letting the crowd’s reaction build on its own. From there the set leaned hard into nostalgia and full arena-scale staging, Nick working the runway in a denim jacket and red bandana, one arm thrown out to the crowd mid-line; Kevin mid-kick further down the stage in a camel blazer, white Gibson Les Paul in hand. “Burnin’ Up,” “S.O.S.,” “Sucker,” “Lovebug,” and “Cool” all made the cut, punctuated by a hometown-storytelling interlude from each brother that slowed the pace just enough to reset the field before the next run of hits.
What made the set work wasn’t just the hits, though, it was the crowd. Cowboy hats and boy-band-era t-shirts sharing the same frame is not a combination Boots and Hearts sees often, and the contrast between the afternoon’s Kissel sing-alongs and the Jonas Brothers‘ shriek-along choruses said more about the festival’s evolving audience than any lineup announcement did.

Saturday: Rising Names and a Country Institution

Saturday was about pedigree, the festival shifting back toward its traditional base with a lineup that built from developing acts into a genuine legacy headliner. The day opened with The Jack Wharff Band, and Thelma & James, the duo of Jake Etheridge and MacKenzie Porter, whose harmonies gave the smaller afternoon crowd something worth arriving early for.

The afternoon’s real momentum came from the pairing of Waylon Wyatt and Sam Barber, both still building their national profiles but drawing crowds that had clearly done their homework, a noticeably younger cluster near the pit for both sets, phones out for the newer material rather than the deep cuts. Barber’s set in particular had a rawer, more stripped-down energy that stood in contrast to almost everything else on the day’s bill.

Jessie Murph took the back half of the evening and brought the energy up a full register. Her distinct voice, genre bending style of country, pop and rap had the crowd wanting more.

The Chicks closed out the day, a booking that needed no explaining to anyone. A genuinely generation-spanning crowd sang along to a catalogue that predates most of the rest of the weekend’s bill, a different atmosphere than the night before: fewer collective shrieks, more quiet, full-throated reverence, and a crowd that seemed to know instinctively when to go loud and when to just listen.

Sunday: Rascal Flatts Closes the Weekend

By the third day, the physical toll of the weekend was visible but it did not stop the party. Sunday’s undercard kept building steadily through the afternoon: Mitch Zorn and Savannah Jade opened things up early on the Front Porch Stage, part of the same wave of rising Canadian names spotlighted all weekend.

James Barker Band then made their long-awaited return to the Main Stage. Kaitlin Butts and Ashley Cooke carried the mid-afternoon, each pulling a noticeably engaged crowd despite the heat. Max McNown and Tucker Wetmore closed out the support slots as everyone prepared for the closer.

Rascal Flatts brought the weekend full circle, closing the festival the way it opened, with a name synonymous with a specific era of country music. The set leaned on the hits, and this was a crowd that already knew every word before the first chorus landed. The late setting sun gave way to a stage lit for a true arena-scale finale, a fitting bookend to a festival that had spent three days proving it could scale up in either direction, pop or legacy country, without losing its own identity.

A crowd that had given the festival three full days and had just enough left for one last singalong before the walk back to the campground.

The Bigger Picture

What stood out most across the weekend wasn’t any single set, it was how deliberately Boots and Hearts used its 15th anniversary to widen its own lane. Celebrating a rookie showcase winner like Leah Holtom with an established crossover act like the Jonas Brothers, on the same three-day bill as The Chicks and Rascal Flatts, made for a festival that is a statement about where country music’s audience actually lives now.

Head to our Facebook page for the full galleries of Day 1, Day 2, and Day 3!

All Photo Credit: Kieran Delport