2024 Headliner – Steven Lee Olsen
Having solidified himself as a chart-topping lyricist and an artist with a global reach, powerhouse vocalist Steven Lee Olsen is one of this generation’s most promising Country singer-songwriters with no plans to slow down. Throughout the past year, Olsen highlighted his ever-evolving artistry and identity as a singer-songwriter, further carving his name in country music. He has garnered over 25 million global streams and a variety of songwriting collaborations. Accumulating a global fanbase, the Toronto-born singer continues to develop his artistry outside of his various co-created #1 chart-topping songs.
Steven Lee Olsen comes armed with incredibly versatile vocal stylings and honest storytelling that reflect his soul, country, R&B, and pop influences.
Check out his website here: Steven Lee Olsen
Joining him on the Winding Roads stage were rising Canadian country stars The Band Caves, Dave Vaillancourt, and Mackenzie Leigh Meyer!
2023 – The Washboard Union
Featuring: Owen Reigling, Lydia Sutherland and Red Cup County
2022 – Tebey
Featuring: Red Cup County, The Doozies and Julien Kelland
2021 – River Town Saints
Featuring: Lemon Cash
2021 – Crown Lands
Featuring: Hunter Sheridan and Matt Gunn
2020 – The Reklaws
Featuring: Kris Barclay
2019 – George Canyon
Featuring: Charlie Major, Marshall Dane and Robyn Ottolini
2018 – Madeline Merlo
Featuring: Ben Hudson and Brad James
2017 – The Road Hammers
Featuring: Kris Barclay
