The Top 10 must-see shows at Winterfolk 2020 in Toronto

February is here, and the countdown for Toronto’s 18th annual Winterfolk Blues and Roots Festival is officially on. As the festival gears up to showcase more than 100 of the genre’s best artists across five stages over three days this Feb. 21, 22, and 23, Roots Music Canada takes a look at the weekend’s top 10 must-see shows sure to warm music lovers to their toes. 

Here they are in no particular order:

History of Blues Guitar and Modern-Day Jam 

Two-time Juno Award-winning and seven-time Maple Blues Award-winning artist Jack de Keyzer will helm this special afternoon double bill. Notably one of the finest blues guitarists on the scene today, Jack will do a solo exploration of the history of blues guitar from Robert Johnson to Jimi Hendrix, followed by a modern-day jam alongside fellow aces Mike McKenna, Danny Marks, Donne Roberts and D’Arcy Wickham. This event is a separate ticketed show, and wristbands are not necessary; tickets are $15 in advance and $25 at the door. 

Feuding Guitars

  • Sunday, Feb. 23, 8:00 .pm. – 9:00 p.m. at Tranzac Club, main hall

Game, set, match! At no time will their fingers leave their guitars as Canadian artists Wendell Ferguson and Tony Quarrington turn the stage into a battleground of sorts in an event guaranteed to entertain.

Women who Write

  • Saturday, Feb. 22, 4:00 p.m. – 5:00 .pm. at the Tranzac Club, main hall

With over 900 songs, 14 albums, a Juno Award, six Canadian Folk Music Awards, and a Grammy Award-nominated song to her credit, Canadian singer-songwriter Lynn Miles knows a thing or two about Women who Write. The befittingly-named showcase will see Lynn alongside fellow prolific singer-songwriters Meg Tennant and Lynn Harrison taking audiences and aspiring songwriters alike through their respective creative processes and long-favoured tunes.

They Put the Folk in Winterfolk

It’s an evening featuring three of Canada’s finest folk music exports. With more than 60 albums and countless awards between them, world-renowned folk music scene veterans James Gordon, Jon Brooks, and Lynn Miles will each take the stage at Saturday night’s special event. This event is a separate ticketed show, and wristbands are not necessary; tickets are $15 in advance and $25 at the door.

Some Picks for the Planet

Running a cold-season festival for 18 years and running, there’s no doubt the organizers of Winterfolk of all festivals are witnessing climate change on the front lines. Given this, it’s fitting that several of the weekend’s events centre around the planet’s well-being and societal consciousness as a whole. 

Emergency Climate Crisis Musical: Written and performed by James Gordon

  • Saturday, Feb. 22, 1:00 p.m. – 2:00 p.m. at the Annex, Annex Commons

Songs for a Better Planet: featuring Saije, Taylor Abrahamse, and Howard Gladstone

  • Sunday, Feb. 23, 4:00 p.m. – 5:00 p.m. at the Annex, Annex Commons

Songs of Change and Conscience: featuring Kyp Harness, Glen Hornblast and Saije

  • Sunday, Feb. 23, 8:00 p.m. – 9:00 p.m. at the Tranzac Club, Tiki Room

Blues and Bluegrass

The festival’s special presentations officially kick off with an evening of all things blues and bluegrass featuring the multi-award-winning, vastly and artistically dynamic stylings of Ken Whiteley, the Layrite Boys, Chris Whiteley and Diana Braithwaite. This event is a separate ticketed show, and wristbands are not necessary; tickets are $15 in advance and $25 at the door.

Suzanne Jarvie 

  • Saturday, Feb. 22, 2:00 p.m. – 3:00 p.m. at the Annex, Annex Commons
  • Saturday, Feb. 22, 3:00 p.m. – 4:00 p.m. at the Tranzac Club, main hall
  • Sunday, Feb. 23, 8:00 p.m. – 9:00 p.m. at the Annex, Wine Bar

Critically acclaimed for having produced a masterfully envisioned album with songs that reverberate within (the) listener’s spiritual and intellectual core, the Suzanne Jarvie Band will take the stage early afternoon to showcase the Canadian Americana singer-songwriter’s stunning sophomore release, In The Clear. Suzanne’s second performance on Saturday is part of the Harmony Hoedown with Clela Errington, Meg Tennant, and Glen Hornblast, and her third of the weekend overall — Sunday, the 23 — is alongside Barbara Lynch as part of the Funny Girls hour. 

Ori Dagan

  • Saturday, Feb. 22, 6:00 p.m. – 7:00 p.m. at the Annex, Annex Commons
  • Sunday, Feb. 23, 9:00 p.m. – 10:00 p.m. at the Tranzac Club, Southern Cross

Multi-award-winning and chart-topping Canadian artist Ori Dagan will bring his rich baritone solo stylings to the stage Saturday evening for a power hour of jazz, followed by a trio performance aptly dubbed Two Crooners and a Croonette the following night with Sam Broverman and Heather Luckhart. 

Black Butch Woman’s Blues

  • Saturday, Feb. 22, 3:00 p.m. – 4:00 p.m. at the Annex, Annex Commons

To call Faith Nolan a folk singer doesn’t come close to doing the award-winning queer

Afro-Scotian singer-songwriter, producer, and activist, justice on her 40-plus-year multi-faceted and richly dynamic career. Hear the voice dubbed “powerful enough to shake the Canadian landscape” Saturday afternoon. 

Yan-Nick Michaud

  • Friday, Feb. 21, 7:00 p.m. – 8:00 p.m. at the Tranzac Club, Tiki Room

Canadian barefoot multi-instrumentalist Yan-Nick Michaud is set to delight audiences with a signature brand of acoustic indie rock-meets-soulful, bluesy-folk. There will be homemade shakers, a rickety wooden Cajon, and an outpouring of love, honesty and humility heartwarmingly spilled out to the audience through song. 


Winterfolk XVIII Blues and Roots Festival

Friday, Feb. 21 — 7:00 p.m. – 1:00 a.m.

Saturday, Feb. 22 — 1:00 p.m. – 1:00 a.m.

Sunday, Feb 23 — 1:00 p.m. – 10:00 p.m. 

The Tranzac Club (292 Brunswick Ave)

The Annex Hotel (296 Brunswick Ave)


Wristbands Available at the Door (While Supplies Last)

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