We can already feel it in the air. Cozy sweater weather is coming but let’s not rush things. September is, hands-down, my favourite season of the year. The leaves are changing and the air is fresh but the sun still shines and gives us that warmth we always wish we could bottle up and carry us through the winter months. While we hold onto the last few weeks of official summer, we embrace every moment as much as possible. So much is happening and we can’t wait to dive right in!

ARTWALK 2.0 — Toronto Downtown West: FREE! Explore the city by foot while checking out public art installations with AR! Map out your route and view some of the most iconic art pieces in the city. Download the Engage Art app and participate in ArtWalk on your own time and pace.  The FREE self-guided audio tour includes over 70 outdoor public art pieces downtown Toronto and six augmented reality experiences of some of Toronto’s most iconic art pieces and storied architecture.

Artwalk 2.0 Toronto Downtown BIA

Le Burger Week: September 1 to 14. Over 600 restaurants across Canada will showcase their creative talents by offering a limited time only  burger. In addition to stuffing our faces with burgers, new this year is the Hambur-games an interactive game that allows participants t rack up points (called YUMS) and redeem them for burgers throughout the two-week event. Le Burger Week also will give back through their charity initiative partnering with three Canadian charities.

Toronto International Film Festival: September 7 to 17. The annual film lover’s festival returns to the city with a massive slate of incredible films to see. Screenings happen at various venues. Best to plan ahead including places to eat and drink. Our top film picks can be found here. Also, don’t forget to check out the TIFF Festival Street on the first weekend around David Pecault Square! Free partner activations, live entertainment and screenings are planned!

The Movie Teller. Photo courtesy of TIFF

The Movie Teller

30 YEARS OF RED CARPET STYLE with George Pimentel: Yorkdale Shopping Centre. September 5 to 30. We may not get the celebrity power this year at TIFF but you can see the incredible collection of the most iconic red carpet moments in this truly extraordinary exhibition. Highly acclaimed celebrity photographer, George Pimentel, is one of the most sought after at major events here in Toronto and globally. You won’t want to miss this!

Cabbagetown Festival: September 9 & 10.
The two-day celebration will feature live music performances and street performers, local artisans to shop, delicious fare from food trucks and pop-up patios, and the ever-popular Cabbage Patch Kid’s Zone. Featuring participation from over 200 local vendors, the 44th annual family-friendly street festival will take over Parliament Street from Gerrard to Wellesley and Carlton Street from Parliament to Ontario.

Toronto Waterfront Festival: September 16 & 17. Returns with a splash! Also returning is the World’s Largest Rubber Duck! This floating yellow beacon of joy is a can’t miss! Visitors to the area will also find music, food, nautical programs and entertainment for the whole family.

SIX The Musical: September 23 to December 17. Royal Alexandra Theatre. From Tudor Queens to Pop Icons, the SIX wives of Henry VIII take to the microphone to remix five hundred years of historical heartbreak into a Euphoric Celebration of 21st century Girl Power! This new original musical is the global sensation that everyone is losing their head over! This one is not to be missed!

Toronto International Festival of Authors: September 21 to October 1. Canada’s largest and longest-running festival of words and ideas, invites audiences to let their imaginations soar through 200+ events and activities. From conversations and readings, to stage performances and writing workshops, as well as crafts and activities for kids, there is lots to enjoy and explore at this year’s Festival. Alongside some of the best fiction and non-fiction authors, poets and storytellers, including Pulitzer, Booker and Giller prize winners, audiences can savour delicious stories at Bite the Book event, celebrate storytelling in all its genres with Pop Fiction, debate contemporary issues at a Critical Conversation, or enjoy the simple pleasures of play in the TIFA Kids programme. The Festival will welcome hundreds of authors and artists from over 20 countries. Registration is now open at FestivalofAuthors.ca.

We’ve Got Guts Forum: September 22. Artscape Wychward Barns. This free public event offers programming that promote the importance of gut health, while empowering attendees to live their best lives through meaningful talks, informative science-backed insights, and hands-on workshops hosted by some of Canada’s top thought leaders. Speakers already announced include Olympian Penny Oleksiak, registered dietician and gut health expert Andrea Hardy, registered clinic psychologist Amber Cohen, singer/songwriter and actress Jully Black, and the amazing life coach Raia Carey! The event is hosted by Activia — pioneer of probiotic yogurt in the Danone family of brands.

Nuit Blanche: September 23 & 24. Various locations across the city. This year’s theme is Breaking Ground and invites artists to explore ideas centred around the natural world and being on the vanguard of change and innovation. Rain or shine. Dress appropriately. Casual shoes a must! Best to take TTC  and walk. Free event for all ages…all night.

Nuit Blanche


Jackson-Triggs Concert Series: the crowd-pleasing performances  extend into mid-September—making summer 2023 all the more exciting for Southern Ontarians. Jackson-Triggs Niagara Estate Amphitheatre is an unforgettable way to experience the best in Canadian music. This open-air amphitheatre has hosted over 150 of Canada’s finest musicians for over two decades. The remaining concert lineup includes performances from hit Canadian artists like Charlotte Cardin, Bahamas and Reklaws.

Base31 Picton: If you’re looking to visit to Picton and wondering what to do? Base31 is a new creative hub that’s been creating quite the buzz over the summer months. This former air base turned seriously cool place to visit offers a terrific concert series as well as art installations. The historical site will continue to offer worthy explorations well into the fall. Check out Dusk Dance and Drone show (last one September 1), Night Watch – an illuminated art walk, a historical walk, yoga, family activities and more. Visit their site for what’s happening. We recommend staying at The Royal Hotel Picton for a wonderful getaway. Link to Libby’s recent write up here.

Stratford: winning our hearts is this charming town with so much to do, see, and eat. Known for it’s world-class theatre, and yes Justin Bieber, there’s plenty to fill a weekend. We recently checked out King Lear (Paul Gross is the lead!) and RENT (Robert Markus – who we loved also was the lead in Dear Evan Hansen in Toronto). The food scene is incredible!  We highly recommend staying at the new Hotel Julie. It’s stunning and within walking distance to everything. Check out Carol’s recent write up here.