1. Go to Just For Laughs

Prepare to laugh until your sides hurt as the highly anticipated Just For Laughs Toronto comedy festival makes its triumphant comeback from Sept. 21 to 30. This uproarious event promises 10 days of non-stop entertainment, featuring an impressive roster of today’s hottest comedians. Get ready to be tickled by the comedic brilliance of Andrew Schulz, the incisive humor of Ronny Chieng, the infectious energy of Leslie Jones, the unapologetic wit of Nicole Byer, the wisdom and charm of Jonathan Van Ness (pictured above), and the uproarious antics of Marlon Wayans, among others. The festival’s dynamic lineup, which also includes cast panels, live podcast recordings and more, guarantees an unforgettably hilarious experience that will leave your spirits lifted and your cheeks sore from laughter. For all the details and ticket information go to Toronto.hahaha.com. 

 2. See Fall for Dance North

The Fall for Dance North 9th Annual Festival is set to captivate Toronto from Sept. 26 to Oct. 7. Offering an inspiring showcase of dance performances, this year’s event underscores accessibility with tickets priced at $15. Noteworthy highlights include Toronto debuts from renowned companies using dance to drive social change, along with the introduction of the Indigenous-led Tkaronto Open dance competition on Canada’s National Day for Truth and Reconciliation. For comprehensive details and ticket information, visit the official Fall for Dance North website at FFDNorth.com.

3. Visit the Gallery Weekend

Gallery Weekend Toronto is set to dazzle from Sept. 21 to 24, hosted by AGAC. With a lineup of 25 galleries showcasing over 70 artists, the event offers a fresh perspective on contemporary art. Divided into three curated routes, this year’s weekend promises more than just exhibitions. Engaging artist talks, immersive tours and captivating performances will awaken your creative senses. Don’t miss the chance to witness Anne Low’s Bury Me at Franz Kaka, explore the intriguing blend of Lawler and Noguchi at Beauty Supply Room, and delve into Alyssa Alikpala’s artistic exploration of environment at Joys. This September, let Gallery Weekend Toronto be your portal to a world of artistic wonder. Go to Toronto.galleryweekend.ca for details.

 4. See Peter Gabriel

Get ready to immerse yourself in the musical brilliance of Peter Gabriel as he takes the stage in Toronto on Sept. 11 at the Scotiabank Arena. A true luminary in the music world, Peter Gabriel has been captivating audiences for decades with his distinctive sound and thought-provoking lyrics. With a remarkable career that spans from his earlier work with the iconic band Genesis to his solo ventures, Gabriel has left an indelible mark on the industry. Known for hits like “Sledgehammer,” “In Your Eyes” and “Biko,” Gabriel’s Toronto concert promises an unforgettable evening, featuring both his timeless classics and new material from his upcoming album i/o. For more information, go to scotiabankarena.com.

5. Go to Intersection Festival

Experience Toronto’s 13th Annual Intersection Festival from Sept. 1 to 3. This innovative celebration of experimental music unfolds across the city’s venues, offering a diverse and immersive musical journey. The festival kicks off at St. Anne’s Church with N.Y.C. experimentalist William Basinski presenting “The Last Symphony,” accompanied by electronic artist Kuuma. Yonge-Dundas Square transforms on Sept. 2 into a hub of eclectic music, featuring acts like Tiger Balme, Naomi McCarroll-Butler and Christopher Tignor. Sept. 3 offers workshops and insights, including Christopher Tignor’s performance and discussion. The festival culminates with a workshop/performance of Julius Eastman’s “Buddha.” The Intersection Festival remains a cultural beacon, blending international and local talent across genres redefining the Labor Day Weekend. For more information, intersectionfestival.ca.

6. See Festival of Authors

Prepare to embark on a journey of imagination at the Toronto International Festival of Authors, running Sept. 21 to Oct. 1, featuring more than 200 events, showcasing the brilliance of Canadian and international storytellers. The festival offers an array of conversations, readings, performances, workshops and kid-friendly activities, featuring authors such as Margaret Atwood, Billy-Ray Belcourt, Patrick deWitt, Emma Donoghue, Anne Enright, Richard Ford, Masha Gessen, Michelle Good, Charlotte Gray, Catherine Hernandez, Casey Plett, Sarah Polley and Makoto Yukimura. For more details, visit FestivalofAuthors.ca.

7. Go to The Master Plan

From Sept. 5 to Oct 1, Crow’s Theatre presents the highly anticipated play The Master Plan, directed by Chris Abraham. Michael Healey’s biting satire, adapted from Josh O’Kane’s book Sideways: The City Google Couldn’t Buy, sheds light on Toronto’s failed smart city venture involving Sidewalk Labs and Waterfront Toronto. With a talented cast, including Mike Shara and Ben Carlson, the play explores the corporate drama and political complexities behind the scenes. For more information head to Crowstheatre.com.

8. See Janelle Monáe

Get ready for an electrifying experience with Janelle Monáe on her Age of Pleasure tour, taking the stage at Massey Hall on Sept. 21 and 22. Joining them for an unforgettable night of music are the talents of Jidenna, Flyana Boss and Nana Kwabena. This event promises to be a sensational showcase of Janelle Monáe’s visionary sound and unparalleled style. With eight Grammy Award nominations under their belt, Monáe is a singer, songwriter, producer, performer and fashion icon who has left an indelible mark on the modern era. Beyond her musical prowess, Monáe is known for her unyielding activism for social justice and the LGBTQIA+ community. 

9. Go to X Avant

10. Go to Venus Fest

Step into the realm of musical evolution at Venus Fest 2023, an upcoming and exhilarating not-for-profit music festival set to unfold from Sept. 21 to 23 at the captivating It’s OK* Studios, located at 468 Queen St W. This event offers more than just music. It’s a celebration of transformation and forward movement in the industry. The festival’s lineup is a tapestry of diverse voices, each with a unique story to tell including the incomparable Allison Russell performing on Sept. 21. Other highlights include the electrifying Sister Ray and the enchanting melodies of Deidre. On Sept. 23, the festival wraps up in a crescendo of musical brilliance with the spirited rhythms of headliners Shannon and the Clams. Check out the Venus Fest website for all the great happenings at Venusfest.net. 

11. Go to Nuit Blanche

The 17th annual Nuit Blanche Toronto, slated for Sept. 23, will transform the city’s landscapes with more than 80 art projects by nearly 250 artists, exploring the “Breaking Ground” theme that delves into environmental and urban issues. Divided into three curated areas, the event features installations in Etobicoke, downtown Toronto and Scarborough, with artists challenging norms and perceptions. Notable works include Leeroy New’s futuristic boat sculptures, Dana Prieto and Reza Nik’s multimedia engagement with a historical site and Divya Mehra’s critique of colonialism through a magical lamp. Visit toronto.ca/nuitblanche for more information.

12. See Topdog Underdog

Set to take the stage at the Berkeley Street Theatre from Sept. 22 to Oct. 8, Canadian Stage presents a captivating rendition of the American classic Topdog Underdog, by Suzan-Lori Parks. This season’s opener features the dynamic talents of Mazin Elsadig and Sébastien Heins in the lead roles, under the skilled direction of Tawiah M’Carthy. Originally premiered in 2002, the play gained historic recognition for Suzan-Lori Parks as the first Black woman to win the Pulitzer Prize for Best Drama. It remains a poignant exploration of brotherhood, race and the perpetuating cycle of violence, offering a compelling perspective on the Black experience in America. For further information, visit canadianstage.com.