The Redwood Theatre on Gerrard Street East helps residents get their groove back; welcomes Bill King as artistic director

First opened as The Classic Theatre in 1914, Gerrard Street East's Redwood Theatre is becoming a popular spot for East Toronto music fans. Photo: Submitted.

In an unassuming yet blossoming region of Toronto, The Redwood Theatre, at 1300 Gerrard St. E. (just east of Greenwood Avenue) is thriving.

The Redwood Theatre was originally built as a vaudeville theatre in 1914. It was a cinema until the late 1950s, when it became a Pennyworths Department Store Warehouse. The interior reflects that history.

Born as The Classic Theatre and home to the most inviting vaudeville performers at the turn of the last century, the Classic strengthened with the times.

In the 1940s and 1950s, the theatre adapted, introducing the ‘talkies.” From 1956 until the late 1980s it operated as Pennyworth’s department store. Then, in 2005, the Zero Gravity Circus rented the theatre, and began presenting cabarets and offering aerial circus classes.

In 2017, Maria Karam and Rob Indrigo took over operations. The couple introduced a farmer’s market and began programming various musical and theatrical events.

As with many clubs and events spaces, COVID-19 placed a heavy burden on those established and those on the upswing, bringing closure as we sat out the darkest hours of the pandemic. Many of the most endearing and dependable establishments vanished. Those who endured reap the benefits.

Prior to COVID, it was all about north, east, west, and south. There were plenty of facilities within driving or TTC distance one could inhabit for a night of live entertainment. Not so much now. The escalating price of real estate and owners unwilling to open entertainment venues is changing the way we view our city.

We now migrate wherever there may be music, social interaction, and demographics that speak to us.

The Redwood Theatre engages an audience willing to factor in a few extra moments of travel time in search of a safe, high-end social experience where music and the arts are the backdrop of a grand night out.

“It was Whisky Jack’s Duncan Fremin who made several attempts to coax me farther east than I’d ventured the past three years,” said Bill King, the new artistic director.

“I spent 30 years biking and riding transit as artistic director for the Beaches International Jazz Festival and now Director of Strategies and Engagement for SING! Toronto’s International Vocal Arts Festival.Those memories of Kew Gardens, the street scene, burn in my heart to this day. I love the community and those bands – Jeff Healey, The Fabulous Thunderbirds, Larnell Lewis, Archie Alleyne, Emilie-Claire-Barlow, Joey DeFrancesco, Trombone Shorty, Angelique Francis – bringing music of this calibre to the east end was always a passion and mission of mine.”

King sees the future, and it’s the Redwood Theatre.

“The moment I met theatre owner Maria Karam, I knew I was entering a special world. It was those chat sessions. The blaze of ideas and how our visions complement one another’s. The long-range plans. Music, art, theatre, training, skills, reaching out,” he said.

After posting various photos on Facebook, programming at the Redwood Theatre took shape. Enter long-time club owner and music promoter Tim Notter of the two-decade running Orbit Room, once a landmark of College Street West side. The Orbit was a casualty of COVID but didn’t diminish the spirit and will of Notter to revive and reinvent.

Notter moved and has been programming the best of the Orbit; Soul Stew, Pretzel Logic, the Dave Murphy Band, LMT Connection, Jordan John and others. Notter and King have teamed up with Karam and are planning a launch of Tuesday night, Get Your Groove Back – a call to a generation who loved getting out for the social, the meet and greet and dance to the soul, funk and reggae classic. They will begin on May 23 with singer Michael Dunston and the Rhythm Express.

In July and August, the Redwood is partnering with SING! Toronto International Vocal Arts Festival and I Love to Sing! which is a summer program free for kids wishing to learn the art of vocalizing. The eight sessions will be led by Elaine Overholt (vocal coach for the Academy Award musical Chicago, CODA, and international sensation Shawn Mendes), Micah Barnes – Music Director of Canada’s Got Talent and Jeannie Wyse, Associate Music Director of the Randolph Academy for the Arts.

Upcoming events at the Redwood Theatre include:

• May 12 — The Sattelites.
• May 13 — Sound Streams.
• May 16-21 — Wee Festival.
• May 20 — Soul Stew.
• May 23 — Get Your Groove Back Tuesdays
• May 27 — Stevie Wonder Tribute.
• June 2 — Lou Pomanti & Oakland Stroke.
• June 8 — Dan Hill.
• June 24 — Jordan John.
• July 15 – Carol Pope: Up Close and Personal.

For more information on the The Redwood Theatre, please visit the website at

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