September is filled with lots to see and do. It really is a beautiful time of year here in Toronto. The days are still warm and evenings are just starting to cool. That back-to-school feeling, yes, we still get that too! But here’s what is on our radar for this month to make the most of everything in Toronto!
Toronto International Film Festival: Various locations. September 10 to 20
The 51st annual Toronto International Film Festival (TIFF) returns celebrating cinematography from Canada and the world. Considered one of the world’s most important Festivals. TIFF brings filmmakers, actors, and film lovers closer together. From World Premiere screenings to intimate talks and unforgettable Red Carpet moments. It’s peak star-spotting season. It’s also when Toronto shines.
Canadian Opera Company Open House: Four Seasons Centre for the Performing Arts, September 5, 3 pm (FREE)
Take a peek behind the scenes with the Canadian Opera Compay at the Four Seasons Centre for the Performing Arts. Discover what’s behind the curtains and the creative magic that brings opera to life.
Wander through the building at your own pace and enjoy live performances, interactive activities, self-guided discovery stations, and opportunities to learn about the artists, craftspeople, and teams who make every production possible. Along the way, you’ll uncover fun facts about the theatre, get a closer look at costumes and props, and find plenty of surprises for visitors of all ages. Admission is free with registration on their site.
Stolen Childhoods: Royal Ontario Museum, September 8 to October 1
Through archival records, photographs, multimedia interviews, and a 7-foot sculpture, Stolen Childhoods shares the history of the Institute and the children who were forced to attend it. Rooted in Survivor Truths and community knowledge, this exhibition centres Indigenous voices and the intergenerational impacts that continue today. Visitors are invited to reflect, learn, and take part in ongoing conversations about Truth, justice, and reconciliation.
Stolen Childhoods presents the lived experiences of children at the Mohawk Institute, the longest-running Indian Residential School in Canada, located just 100 km from downtown Toronto in Brantford, Ontario. The exhibition was created by the Survivors’ Secretariat with support from Know History and funding from the Museums Assistance Program.
Toronto Biennial of Art: Various Locations. September 26 to December 20
Titled Things Fall Apart, the Biennial draws on the enduring resonance of the phrase across literature and music—from Chinua Achebe’s 1958 novel (itself referencing W.B. Yeats’s The Second Coming) to its rearticulation in The Roots’ 1999 album—as a way of reflecting on periods of political and social transformation. Bringing together over 30 artists and collectives, including 17 newly commissioned works, the exhibition is shaped by Glenn’s research-driven, site-responsive approach and explores rupture as a generative framework, tracing interconnected histories across global waterways anchored in the Great Lakes region.
The Tower That Built The City: Ted Rogers Cinema, September 19
The CN Tower has defined Toronto’s skyline for 50 years. It was first intended to be a broadcast transmssion tower but became an iconic landmark and attraction that is recognized worldwide. Filmmaker Mark Myers offers more than a “how it was built” type of documentary. It’s a fascinating look at how this skyscraper became a cultural symbol that put Toronto on the global map. It’s a love letter and time capsule Torontonians won’t want to miss. Myers will join in a post screening Q&A.
Hell’s Kitchen: CAA Ed Mirvish Theatre, September 23 to October 24
HELL’S KITCHEN is the hit musical from 17-time Grammy Award winning Alicia Keys — inspired by her life, her music, and her community. This one is high on our must-see list!
The journey begins with Ali, a 17-year-old girl full of fire, searching for freedom, passion, and her place in the world. Along the way, you’ll meet the musical mentor who changes her life, her dynamic family, and the neighbourhood that helps her grow. Relatable, raw, and refreshingly fun, HELL’S KITCHEN is a celebration of finding yourself, your purpose, and the people who life you up!
Just for Laughs Toronto: Various locations. September 24 – October 3
The world’s largest comedy festival returns to the city and we can’t wait! Expect a mix of breakout comedy acts, favourite productions, live podcasts, family-friendly programming and much more. Already watching our eye? Headed Rivalry: An Unauthorized Musical Parody, Loud Asians, David Lynch’s Seinfeld. Also, John Cleese, Joe List and Pete Davidson are all doing shows. More to come!
Pre-Existing Condition: Coal Mine Theatre, September 6 to 27 (Canadian Premiere)
A New York Times Critics’ Pick, PRE-EXISTING CONDITION offers an “unfiltered examination of how violence imprints itself on the body and soul” (New York Theatre Guide), centred around an unnamed woman navigating the aftermath of a harmful relationship. When the play first ran in New York at the off-Broadway Connelly Theatre, a rotating cast which included Deirdre O’Conell, Edie Falco, and Canadian Tatiana Maslany, inhabited the lead character. COAL MINE’s production directed by Canadian icon Linda Kash, will feature a single actor– the luminous Amy Rutherford–in the role, joined by Lindsay Leese, Diana Bentley, and Philip Riccio
WALDEN: Icarus Theatre, The Theatre’s Centre BMO Incubator, September 10 to 27
A moving and poignant one-act set in the near future, Walden explores what connection and home means when the Earth is expiring, through the lens of two astronaut sisters. The play stars a heavy-hitter cast, including 2025 Dora Nominee Charlotte Dennis as Cassie, 2026 Dora Nominee Oshen Aoun as Bryan, and Icarus company member Emily Anne Corcoran as Stella. Produced by Anthony Goncharov.
Cabbagetown Festival: September 12 and 13
The 47th annual Cabbagetown Festival returns! Toronto’s longest running street festival is a two-day, family-friendly event that’s free-to-attend! Discover over 250 local vendors, artisan shops, food trucks, pop-up patios, outdoor games, interactive installations, and a Kids Zone. There will also be over 200 local performers including EDM DJs, Indigenous talent, blues and rock bands, instrumental ensembles, stilt walkers, interactive dancers, magic acts, drag performers and more!
Bar Mauro Guest Shift at Library Bar: Fairmont Royal York, September 15, 6-10 pm
Ranked Number 2 on the North American’s 50 Best Bars and named The Best Bar in Mexico 2026, Bar Mauro is bringing its distinctive take on 1970s Italian Aperitif culture to Toronto for one night only. Founded by brothers Ricardo and Eduardo Nava as a tribute to their grandfather’s love for Italian Aperitivo, Bar Mauro has become of one of Mexico it’s most acclaimed cocktail destinations.
For the evening, Eduardo Nava Mendoza and Brisa Marilim Santos will take over Library Bar, bringing Mauro’s signature cocktails and Aperitivo experience from Mexico City to Toronto. Reservations here.
Word on the Street: David Pecault Square, September 26 & 27
It’s a giant book party at Canada’s largest literary festival! This family-friendly book event will feature multiple stages packed with exciting panels and hands-on activities. Discover panel discussions about gripping psychological thrillers, cozy fall mysteries and spicy romances. Explore deep conversations an explore the history of Toronto, how food shapes our identity, and the story of Canadian electronic music.
There is something for every reader including kids! Bring the littles to the Kids Activity Tent for read-aloud story times, hands-on workshops, drawing sessions and make your own puppets!
What The Festival: Youngplace at Sweet Action Theatre, and Small World Music Centre. September 24 to 27
This an annual celebration of all things Drag, Clown and Puppetry returns for its 3rd year in Toronto. is a wild, live theatre festival presenting the best in ‘strange-making’ live entertainment. The 2026 festival will host two performances each of Hansal and Geetal by Two2Mango, Bubkus by Jesse Buck, and Drag Me To The Opera with Aida Cupcake.
DroneArt Show: Harry Potter: YZD, 590 Wilson Avenue (Formerly Downsview Park), September 25 & 26
Fans in Toronto will have the opportunity to experience some of the most beloved moments from the Harry Potter film series reimagined in a first-of-its-kind open-air drone spectacle. The show will blend advanced drone choreography with breathtaking aerial displays set to the enchanting soundtrack and dialogue from the Harry Potter film series. The experience features 1,200 illuminated drones soaring across the night sky in perfect synchronization with a live violinist bathed in a stunning canvas of light and dialogue from the films. Also, before the show, guests can enjoy a celebratory atmosphere featuring food and beverage offerings, along with the opportunity to purchase coveted merch.
The Birra Moretti Sunday Social: September 6, 27 and October 4
Lake Inez is the spot to be for this intimate dinner series where guests can pull up a chair, reconnect over great food and conversation, and enjoy life’ simple pleasures. Inspired by Lake Inez’s coveted Mystery Patio experience, The Birra Moretti Sunday Social brings a new twist to the restaurant’s signature spirit of surprise and storytelling. This is actually a giveaway contest with each experience valued at $200. More details @birramoretti.ca on Instagram.
And Out of Town…
Fall Road Trip to Huron County
Huron County is a sprawling terrain home to stunning landscapes and, of course, some of Ontario’s most beautiful beaches hugging the shores of Lake Huron. But this county is more than sand-filled escapes. There’s a rich terroir in Ontario’s “West Coast“, a region brimming with agriculture nourished by not only the soil, but the people themselves. And fall’s harvest season is the perfect time to visit! Check out Libby’s write up here!!!
The Maids: Talk is Free Theatre. Barrie by the Bay, 80 Bradford Street, September 17 to October 3
Based on a true story, the darkly comic and unsettling The Maids tells an account of two sisters employed as servants in a wealthy household who engage in elaborate role-playing games, each taking turns as their superior, Madame. However, thanks to long-suppressed frustrations and desires, their private rituals intensify with devastating consequences. This celebrated drama is a provocative examination of social hierarchy and the masks people wear to survive in a world filled with inequality.
Apple Picking Season! across Ontario
There are many great apple orchards just outside the GTA offering pick-your-own experiences. Everything from straight forward farms to family-style entertainment (wagon rides, mazes, bakeries, etc) are ready and waiting. A perfect outing! Some of our favourites: Carl Laidlaw Orchards, Downey’s Apple Farm, Brantview Apples + Cider, Chudleigh’s, Dixie Orchards. Check individual apple farms for hours and details. Learn more about the variety of apples grown in our province here.