The Flato Markham Theatre Opens its 41st Season with a Packed October

For most, the fall is when things feel new again; whether it’s the school year, colours changing, or indeed a new season of theatre. This October sees the Flato Markham Theatre’s 2026/27 Diamond Season get underway with Canadian legends, world-class jazz, comedy, Indigenous artists, magic, rock and a few opportunities for audiences to become part of the show themselves.

The Diamond Season officially launches on Saturday, October 3 at 8pm with Dan Hill & Andy Kim: In Story & Song, a rare pairing of two Canadian Music Hall of Fame songwriters. Together, they’ll share the stories and songs that made them household names, including staples like Sometimes When We Touch, Sugar, Sugar and Rock Me Gently. Kim has sold more than 30 million records over his career, while Hill’s work has extended beyond his own recordings to writing and producing for artists including Céline Dion and George Benson.

The jazz series begins just days later on Thursday, October 8 at 8pm when JUNO Award-winning trumpeter and vocalist Bria Skonberg brings her modern spin on vintage jazz to Markham. A Canadian-born artist who has established an international career from her base in New York, Skonberg combines traditional jazz and swing with contemporary influences and an engaging stage presence.

The following night, Friday, October 9 at 8pm, Classic Albums Live returns for the first of three performances this season, this time tackling Led Zeppelin II. As always, the premise is refreshingly simple: a collection of exceptional musicians recreates the album note-for-note and cut-for-cut.

On Friday, October 16 at 8pm, She Carries the Song brings together Indigenous artists Celeigh Cardinal, Mimi O’Bonsawin and Lacey Hill for an evening rooted in storytelling, song, resilience and connection. The collaborative performance puts three distinctive voices together on one stage, offering an opportunity to hear contemporary Indigenous music through the experiences of the women creating it.

Comedy takes over on Thursday, October 22 at 8pm with Tom Arnold and My Crazy X-Wife. The actor and comedian, whose career has stretched across stand-up, television and film for decades, brings an evening of personal stories and characteristically unfiltered observations to the stage.

The very next evening, Friday, October 23 at 8pm, audiences get a considerably more participatory experience with Sing Pitch Perfect with Deke Sharon & Splüsh. Sharon, the influential arranger, producer and music director associated with the Pitch Perfect films, leads an interactive a cappella experience that includes stories from the movies, a performance by Splüsh and an opportunity for the audience to actually make some music themselves.

On Saturday, October 24, Chris Funk the Wonderist brings Redefining Wonder to Markham for performances at 2pm and 7pm. Seen on America’s Got Talent, Penn & Teller: Fool Us and Masters of Illusion, Funk combines illusion with live music, interactive video and audience participation. Instruments including violin and guitar become part of the magic rather than simply accompanying it.

The final days of October then offer two performances seemingly made for the impending spooky season.

Mariachi Herencia de México brings its Día de Muertos Tour to Markham on Thursday, October 29 at 8pm. The acclaimed Chicago-based ensemble represents a new generation of mariachi musicians, combining the traditions of the form with youthful energy and contemporary presentation in a celebration timed just days before Día de Muertos.

Then, on Friday, October 30 at 8pm, Jeans ’n Classics provides a suitably theatrical soundtrack for Halloween weekend with Time Warp: The Music of Rocky Horror. The company applies its familiar combination of rock musicians, vocalists and orchestral arrangements to the music of the enduring cult phenomenon, bringing songs including Time Warp into the concert hall on perhaps the most appropriate weekend of the year. (Markham)

As usual, October also features strong community presentations.

The Kindred Spirits Orchestra opens its season with Elegance and Imagination on Saturday, October 17 at 8pm. The program includes Ravel’s Ma mère l’Oye, Mozart’s Concerto for Flute and Harp and Franck’s Symphony in D minor. Toronto Symphony Orchestra principal flutist Kelly Zimba Lukić and harpist Andrew Chan are the featured soloists.

The venerable Markham Concert Band launches its 49th season with Strike Up the Band on Sunday, October 25 at 2pm. One of Canada’s largest community concert bands, the ensemble has particularly deep connections to the Theatre: members of the band were involved in its 1985.

Markham at the Movies also returns on Tuesday, October 27 at 7pm as part of its 2026/27 season of screenings. The volunteer-run community organization has established a regular home at the Theatre for independent, Canadian and international cinema, with individual tickets priced at $15.

With Canadian songwriting legends, jazz, classic rock, Indigenous storytelling, comedy, magic, a cappella, mariachi, orchestral music and some of Markham’s own community performers sharing the stage, October makes a fitting introduction to a Diamond Season built around discovery as much as familiarity.

Tickets and full show information for all October performances are available through the Flato Markham Theatre Box Office.

Photo: Dan Hill and Andy Kim kick off this year’s Diamond Season