Welcome To Dashville Tour: Dasha and Dawson Gray - Winnipeg, MB

The Park Theatre was buzzing with anticipation on September 16, 2025, as country pop singer-songwriter Dasha kicked off her Welcome To Dashville Canadian Tour in Winnipeg. With her highly anticipated new EP, Anna, on the horizon, which is set for release on October 10 via Warner Records, the night not only marked the first date of the tour but also gave fans the rare thrill of hearing some unreleased music live for the very first time.

Opening the evening was rising Canadian country artist Dawson Gray, who brought an undeniable warmth to the stage. Blending heartfelt ballads with upbeat, radio-ready hooks, Gray immediately connected with the sold-out Winnipeg crowd, offering a perfect introduction to the night. His set showcased a promising young talent whose name will no doubt become more familiar across the country in the years ahead.

Dawson Gray. All photos by Samuel Stevens.

The moment Dasha stepped on stage, the room transformed like a snap of the fingers. Backed by a tight, high-energy band, she dove straight into the fan favourite tune “Not at This Party” before unveiling the first of three unreleased tracks from Anna, “Work On Me.” The song carried a polished but emotionally raw edge, instantly proving why Dasha is one of country pop’s brightest rising stars.

Her set struck a balance between her viral hits and a few deep cuts, including the reflective “Didn’t I?” and party-ready anthem “Way Too Drunk.” Midway through the set, she leaned into her influences with an entertaining, fiery cover of Gretchen Wilson’s 2004 hit “Here for the Party” that had the whole room singing along.

But the highlights of the night were undeniably the new songs. “Give Me A Second” and “I Don’t Mean To” revealed Dasha’s evolving artistry—polished yet vulnerable, catchy yet lyrically poignant. Fans were hanging on every word, eager for a glimpse into the upcoming EP. Her performance of “Oh, Anna!” added a poignant, emotional punch to the set, tying directly into the new record’s narrative.

Dasha. All photos by Samuel Stevens.

However, the energy never let up, with tracks like “Heartbreaker From Tennessee” and “Ain’t It Baby” showcasing her mix of sass and sincerity. By the time she reached the set closing number “Bye Bye Bye,” the crowd didn't want the show to come to an end and were chanting for more. For the encore, Dasha returned with the emotional “What Happens Now?” before closing with a crowd-shaking, extended version of her breakout hit “Austin (Boots Stop Workin’).” She invited a number of kids to do the viral dance with her on stage. As the song played out, it stretched into a cathartic, yelling singalong, transforming the intimate Park Theatre into what felt like a stadium-ready chorus of voices.

As the first stop on the Welcome To Dashville Canadian Tour, Winnipeg was treated to a special kind of magic—an artist fully leaning into her momentum, testing out her new material, and connecting with fans in a way only a live show can achieve. With her forthcoming Anna EP poised to push her even further into the spotlight, Dasha proved that she’s not just a viral success but a genuine star with staying power.

For those lucky enough to catch this tour throughout Canada, expect a night that blends vulnerability, empowerment, and a whole lot of fun—true to the spirit of Dashville.