Events happening in Oakville.

Thu, Nov 5 – Sun, Nov 15

A Few Good Men

Aaron Sorkin's legendary courtroom drama arrives in Oakville. This gripping play, which captivated Broadway before becoming a blockbuster film, features razor-sharp dialogue and intense moral dilemmas. The story follows a group of military lawyers assigned to defend two Marines in Guantanamo Bay. As the trial unfolds, they uncover a high-level conspiracy designed to eliminate weaker soldiers in the name of patriotism. For more information, contact [email protected].

Queen Elizabeth Park Community and Cultural Centre (Black Box)

Friday, November 13th

8:00PM

Story Slam: While You Were Sleeping...

Big Ticket, Studio Sessions Did you know that you spend a third of your life sleeping? Have you ever wondered if your wildest dreams are only fantasy? What if your dreams were a blueprint for your waking life? Come find out what happens "While you were sleeping…" and you may see yourself in a whole new light. Join us for a mysterious, boundary-pushing night where laughter, tears, and live music colide, when six bold storytellers will take the stage to weave a tapestry of patterns, connecting their deepest dreams with their daily realities. Together, we’ll discover how these invisible threads tie us all together and reveal just how much power our sleep holds over our day. (Spoiler: it’s more than you think!). Story Slams are in support of CAMH The Centre for Addiction and Mental Health. Donations will be accepted at the CAMH booth at the event. Space is limited for this intimate evening of live music and community storytelling.

Oakville Centre — Studio Theatre - Lower Level · $30

Friday, November 13th

8:00PM – 10:00PM

Story Slam

Story Slam Location: Oakville Centre for the Performing Arts, 130 Navy St, Oakville Time: Starts 8:00 p.m. Join in as Oakville Centre celebrates a community that recognizes the dignity and worth of every person. Filled with laughter and tears their Story Slam Series provides an authentic and powerful interaction between storytellers and audience. Each story is a soul-searching exercise as it takes an intense creative process to create and present a heartfelt narrative. As each storyteller processes their world inside, they can discover enlightenment. This method is inspired by the three main stages of the “Hero’s Journey”, a narrative pattern identified by Joseph Campbell, world-celebrated mythologist. He asserts that storytelling and myths relate to our search for truth, meaning, and significance.

Oakville Centre — Studio Theatre - Lower Level · $30

Saturday, November 14th

8:00PM – 9:00PM

Miigis: Underwater Panther

Miigis: Underwater Panther Location: Oakville Centre for the Performing Arts, 130 Navy St, Oakville Time: Starts 8:00 p.m. Miigis is a powerful contemporary dance work inspired by the epic journey of the Anishinaabe along ancient water routes from the Atlantic Ocean to the Great Lakes. Choreographed and directed by Sandra Laronde in collaboration with the performers, this 50-minute performance brings to life themes of origin, memory, spirit beings, and the Seven Fire Prophecies—carried forward through striking movement, music, and visual design. Red Sky Performance is a global leader in contemporary Indigenous arts and culture. We bring bold and inspiring new works of dance, theatre, music, and multimedia to audiences across Canada and around the world. Red Sky is an Indigenous-led company that celebrates Indigenous ingenuity and resilience through powerful storytelling and artistic innovation.

Oakville Centre — AEG Liebherr Auditorium · $25

Fri, Nov 20 – Sun, Nov 22

Glengarry Glen Ross

Written by David Mamet and directed by Yo Mustafa, this production follows a group of struggling real estate salesmen in a cut-throat office environment. Facing pressure to succeed and fighting for their livelihoods, the characters resort to manipulation — of clients and each other — in a ruthless battle for survival. As the stakes rise, ambition blurs into corruption, and deception, rivalry, and desperation take center stage. Content warning: Strong language, profanity, sexual references, and mature themes.

Oakville Centre — Studio Theatre - Lower Level · $32

Fri, Nov 27 – Sun, Nov 29

The Nutcracker

The Nutcracker 🎄 brings Tchaikovsky's beloved score to life in this traditional holiday tale. Audiences follow Clara, her Nutcracker, and the magician Herr Drosselmeyer through a whimsical journey to the Land of Snow and the Kingdom of Sweets. The Oakville School of Classical Ballet's production features the school's students under the artistic direction of Amanda Paterson. The performance is family-friendly. For more information, contact the Oakville School of Classical Ballet at [email protected], 905-815-2021, or toll-free 1-888-489-7784.

Oakville Centre for the Performing Arts

Thursday, December 3rd

8:00PM

Marsh Marigolds: An Agricultural Thriller

Big Ticket is a drama from the creators of the beloved Wingfield Farm series. The work blends rural mystery, dry wit, and farm-fresh romance into what the creators call "a rural noir — as if Raymond Chandler got lost in Persephone Township." The story centres on Hope, Walt Wingfield's grown daughter, who now works at Queen's Park. Her former boyfriend Ray has returned to Persephone Township and works at the last printed newspaper in Hillhurst Country. As Ray and Hope navigate their lives, the newspaper's editor — a character beloved by fans of the Wingfield shows — begins to piece together mysterious elements the two stir up in the world of agriculture.

Oakville Centre — AEG Liebherr Auditorium · $50

Sat, Dec 5 – Fri, Dec 18

Company

What does it mean to be alive? Decades after its debut, Stephen Sondheim's Company remains as funny and thought-provoking as ever. This Tony Award–winning musical features a brilliantly written score that explores the human experience through an authentic portrayal of modern relationships — marriage, friendship, and everything in between. Theatre Sheridan's production offers a fresh and biting comedic edge, delivering an honest and hilarious look at connection and solitude in contemporary life. Company runs December 5–18, 2026, in the Studio Theatre at Sheridan Trafalgar Campus, 1430 Trafalgar Rd, Oakville. For more information, contact [email protected] or call (905) 815-4049.

Studio Theatre - Sheridan Trafalgar Campus

Saturday, December 5th

1:00PM – 6:00PM

Lady Next Door

Two neighbours share a common courtyard — and they couldn't be more different. Vana is orderly and organized; Huguette is exuberant and messy, delighting in loud music while hanging laundry, camping in her yard, and practicing acrobatic bike stunts. What troubles Vana most are Huguette's perpetually overflowing garbage cans. Through conflict and conversation, the neighbours begin to understand each other, and an unexpected friendship blooms. A female clown duo brings this story to life with physical comedy and heart.

Oakville Centre — AEG Liebherr Auditorium · $20

Sunday, December 6th

5:00PM – 9:00PM

West End Jazz Presents: Season Finale Gala Night

The West End Jazz series presents an evening of dinner theatre featuring the Swing Shift big band, one of Canada's best jazz orchestras, alongside four accomplished vocalists. Attendees may choose to enjoy dinner, attend the show only, or both. Doors open at 4:00 PM, dinner is served at 5:00 PM, and the show begins at 6:00 PM.

Oakville Conference Centre

Wed, Dec 9 – Fri, Dec 18

The Addams Family

Normal is overrated. Theatre Sheridan presents THE ADDAMS FAMILY, a hauntingly hilarious exploration of family, secrets, and individuality. In one fateful night, relationships are tested and truths are disclosed as the Addams family confronts their worst nightmare: change. The story unfolds in the kooky world of the living, dead, and somewhere in between, celebrating what it means to be an Addams. For more information, contact [email protected] or call (905) 815-4049.

Macdonald Heaslip Hall - Sheridan Trafalgar Campus

Sat, Dec 19 – Sun, Dec 27

A Wicked Christmas Carol - A Holiday Pantomime

Christmas, Musical Theatre presents a hilarious mash-up of *A Christmas Carol* and *The Wizard of Oz*. Elphabeneezer Scrooge, the holiday-hating Wicked Witch of the West, is hidden away in her castle trying to ignore Christmas. On the other side of the yellow brick road, the secretly evil Wizard of Ozville plots to get rid of her for good. Glinda is determined to save her old friend from the Wizard's schemes — with the help of three spirits, a bit of time travel, and the audience's magical powers, cheers, and boos. Attendees are invited to join the action and help save the day. Tickets are available and recommended in advance.

Oakville Centre — AEG Liebherr Auditorium · $35

Thursday, December 31st

1:00PM

Grand Illusion: Edllusion

The Grand Illusion Show is a 90-minute live theatre experience blending grand illusions, mind-reading, comedy, and high-energy theatrical showmanship. A dynamic cast of professional assistants and dancers performs stunning visual illusions, shocking reveals, and crowd-pleasing comedy designed to engage audiences throughout. The production is suitable for all ages and works well for family outings, friend groups, or group nights out.

Oakville Centre — AEG Liebherr Auditorium · $25

Thu, Jan 21 – Sun, Jan 24

Plaza Suite

Neil Simon's Plaza Suite presents three interconnected comedies set in Suite 719 at The Plaza Hotel in New York. The first follows nervous parents preparing for their daughter's wedding; the second features a Hollywood producer attempting to rekindle a romance with an old flame; the third depicts a long-married couple navigating their anniversary celebration. Each story explores love, chaos, and the messy, human moments of relationships through sharp wit and memorable characters.

Oakville Centre — AEG Liebherr Auditorium · $39.50

Friday, January 29th

7:00PM

No Excuses, No Limits

No Excuses, No Limits 🎤 ILL-Abilities is an international award-winning breakdance crew comprising Bboys with disabilities. The ensemble has performed in over 25 countries and reached more than 1 million audiences globally. This production takes audiences on a journey through each dancer's personal story, combining dance, music, and audience interaction to explore the limitless possibilities within any person. The show sold out 10 sessions at Kennedy Center in Washington D.C., USA. The crew's name plays on the word "ill," a term from hip-hop culture used to describe something positive and exceptional. ILL-Abilities uses dance, optimistic attitudes, and personal narratives to inspire and spread positive thinking.

Oakville Centre — AEG Liebherr Auditorium · $20

Saturday, February 27th

7:30PM

A Brief History of Smoking Cigarettes

A Brief History of Smoking Cigarettes is a one-woman show that weaves together Deanna's personal relationship with cigarettes and the global history of the tobacco industry. Using puppets, live music, video, and audience interaction, the performance explores themes of colonization, capitalism, and the commodification of natural resources through the lens of one of the world's largest industries. The show combines true stories, wide-ranging reflections, and playful engagement with the audience. It examines how the tobacco industry has shaped both global history and individual lives, told with both humor and heart. Note: The production may include smoke and haze effects, but no tobacco products will be burned. Recommended for adult audiences; minimum age 16+.

Oakville Centre — Studio Theatre - Lower Level · $25

Saturday, February 27th

8:00PM

Debra DiGiovanni & Caroline Rhea

Caroline Rhea is a stand-up comedian and actress best known for playing Hilda Spellman on 'Sabrina the Teenage Witch' and for comedy specials on HBO, Comedy Central, and Showtime. She voices Linda Flynn Fletcher on Disney's 'Phineas and Ferb,' has appeared in films including Hallmark's 'A Mrs. Miracle Christmas,' and has a recurring role on NBC's 'Lopez vs. Lopez.' Rhea has hosted her own talk show and been a regular panelist on 'Funny You Should Ask,' 'Match Game,' 'Name that Tune,' and 'Hollywood Squares.' She performed at the Edinburgh Comedy Festival this year and recently filmed her 7th comedy special at the Sydney Opera House. She tours comedy clubs worldwide and hosts and auctioneers for numerous charities. Debra DiGiovanni is a stand-up comedian and performer originally from Toronto, now based in Los Angeles. She appears at comedy festivals including Moontower, High Plains, JFL Sydney, and JFL Montreal. Her comedy album 'Honourable Intentions' won the Juno Award for Comedy Album of the Year in 2025; her album 'Lady Jazz' was nominated for the same award in 2019. DiGiovanni has appeared on CONAN, The Tonight Show, and Comedy Central's 'Stand Up Featuring,' and released a comedy special on Season 2 of 'Unprotected Sets' for Epix. She also appears on the Amazon original series 'Last One Laughing.'

Oakville Centre — AEG Liebherr Auditorium · $70

Friday, March 12th

8:00PM

Päter

Päter is an Iran-born, Toronto-raised artist whose Alt Pop/Rock Drama blends raw storytelling with complex soundscapes and sharp lyricism. Their music swings between irreverence and sincerity, moving audiences to dance, feel, and sing along. Päter has been featured on CBC and Exclaim!, and has toured across Canada, Germany, and the Netherlands.

Oakville Centre — Studio Theatre - Lower Level · $35