2025 Headliner – JoJo Mason

JoJo Mason has been on a continued mission to find his own unique voice and connect with fans through his music. With an incredible six Top 10 tracks, he has earned a CRIA Gold-certification for his single “Better On You”, and accumulated over 50 million career streams to date.

The core question that drives JoJo Mason’s approach to music and life is, ‘Why not?’. That’s heavily influenced his current single ‘Bottom Shelf’; an immensely hooky country track that finds the Vancouver-based country artist exploring a new direction grounded in his long-time musical fascinations and unfailingly positive outlook.

In the roughly two years since Mason’s released new material, he has taken the opportunity to reinvent himself, expanding on his signature take with a country soul sound that’s a rarity these days.

Check out his website here: JoJo Mason

Joining him on the Winding Roads stage were rising Canadian country stars Daybreak Moonshine, Steve Waters Band, and Julia Middleton!

2025 – JoJo Mason

Featuring: Daybreak Moonshine, Steve Waters Band, Julia Middleton

2024 – Steven Lee Olsen

Featuring: Dave Vaillancourt, The Band Caves, 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 – 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

2016 – Aaron Pritchett

Featuring: The James Barker Band