Owen Riegling was singing "Old Dirt Roads" at bar gigs and country fairs in Ontario for years before it went anywhere. He wrote it in a college apartment, he told SOCAN, trying to think like a songwriter instead of chasing a hit. Winning the 2022 Boots & Hearts Emerging Artist Competition got him signed to Universal Music Canada, and the song is double platinum now.
He's from Mildmay, a farming town of about 1,200, and the stage work stacked up quickly after that: support dates for Brett Young, Jake Owen, Tyler Hubbard, Chase Rice and Dierks Bentley, then his biggest Canadian headline run yet in late 2024. In April 2026 he played Toronto's Massey Hall on the 18th and made his Grand Ole Opry debut four days later. That fall's In The Feeling Tour covered 25 dates across the U.S. and Canada.
The awards came in a pile. Two CCMAs in 2024, Breakthrough Artist and Songwriter of the Year, then Album of the Year in 2025 for Bruce County (From The Beginning), along with a Juno nomination. In The Feeling, his second album, came out April 17, 2026, through Universal Music Canada and Big Loud, and he and producer Oscar Charles played nearly every instrument on it.