September: The Western Fair, Trinbago Toronto Festival, TO Live: Upfront Festival and more!

The inaugural Upfront Festival is a weekend-long celebration of Indigenous talent from across Turtle Island and beyond. Featuring three days of extraordinary music, comedy, puppetry, free workshops, and more, right in the heart of Tkaronto. With performances by William Prince, Drezus, Cris Derksen, Shawnee Kish, Semiah, and more. Learn more.

The Western Fair, one of Canada’s oldest community traditions, welcomes audiences for 10 days of fun every September!  As one of Canada’s major fairs, and a top 100 event in Ontario, the ten-day extravaganza is back and is packed with hundreds of ways to find your ‘happy place’ this September 6-15, 2024. The Fair is embarking on the production of several new components in 2024, including the “Risky Play Summit” is a social-good-based ‘urban arts’ festival/and an expanded “Western Fair Concert Series”.  Learn more.

Calling all couples, singles, polycules, platonic soulmates, situationships, and awfully devoted roommates. This September, you’re invited to Talk is Free Theatre’sI DO, I DON’T, I DARE! a celebration and subversion of marriage, weddings, and commitment. Enjoy immersive performances by a line-up of incredible artists wedded to their crafts, in unexpected locations around Barrie. You’re guaranteed a warm and whacky reception. Say yes to the fest! Learn more.

Tickets are now on sale for performances throughout Aurora Town Square’s highly anticipated Grand Opening, September 21 – October 13. This momentous occasion will be marked by a variety of indoor and outdoor entertainment, including exclusive previews from partners and captivating performances spanning many genres. Learn more.

The World of Jazz Festival, B-Jazzed’s annual signature event, hosts over 100 musicians in Downtown Brampton across two days. Jazz has evolved significantly since its inception, influenced by global cultural and socio-economic factors. The Festival showcases ensembles that embody diverse influences and provides a platform for local students, hobbyists, and professional musicians to perform. Programming will include renowned artists like Michael Kaeshammer and the Count Basie Orchestra Learn more.

After a successful debut in 2022 and attracting 22,000 visitors in 2023, the Trinbago Toronto Festival returns for its 3rd year on September 7 and 8, at Nathan Phillips Square. Enjoy more vendors serving Trinidad and Tobago cuisine, vibrant cultural performances, and special booths from sponsors like Visit Trinidad and Visit Tobago.

Don’t miss the special illuminations of the CN Tower and Toronto sign in Trinidad and Tobago’s national colors on September 7th! Learn more.

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