From Sunshine to Sweater Weather: The Best Late Summer & Early Autumn Entertainment in Toronto
Toronto’s late summer and early fall offer the best of both worlds—sunny patios, golden hour strolls, and that first whiff of crisp autumn air. Whether you're holding onto summer or already reaching for your flannel, there’s no shortage of ways to enjoy the city during this seasonal crossover. Here's your go-to guide for what to do in Toronto as summer fades into fall.
1. Take a Fall Colours Walk (Before the Crowds Hit)
Toronto starts showing its autumn hues in early September. Get your steps in (and your phone out) at:
High Park – golden maples and quiet trails
Don Valley Trails – perfect for cycling or hiking
Evergreen Brick Works – nature meets city with a side of farmer’s market
2. End-of-Summer Concerts & Music Fests
Toronto doesn’t shut down the amps after August. Late summer/early fall concerts still bring the energy:
CityView Drive-In and Budweiser Stage host outdoor shows into September
Catch intimate live music at The Drake Underground or Danforth Music Hall
TIFF music nights sometimes pop up during festival week
3. TIFF Season is Here
September means one thing for film lovers:
The Toronto International Film Festival. Catch red carpet moments, sneak peeks of Oscar contenders, and maybe even bump into a celeb in Yorkville.
Pro tip: the free screenings and walk-up ticket lines are great for spontaneous fun.
4. Late Summer Picnics & Outdoor Markets
That sweet spot where it's not too hot, not too cold? Ideal picnic weather.
Lay down a blanket at Trinity Bellwoods, Riverdale Park, or Toronto Music Garden
Stroll through the St. Lawrence Market, Kensington Market Pedestrian Sundays, or Leslieville Flea
5. Soak Up the Final Days of the CNE
Catch the last few days of the Canadian National Exhibition if you're fast. Fair food, rides, and the Air Show close out summer with a bang.
6. Fall Beer & Food Festivals
Toronto turns into a foodie paradise once the leaves start changing. Don’t miss:
Toronto Oktoberfest (yes, lederhosen optional)
Pumpkinfest at Downsview Park for family fun
Smorgasburg Toronto – every Saturday until mid-fall
7. Golden Hour on the Waterfront
The best sunsets of the year happen in September. Head to:
Polson Pier – skyline views with a breeze
Trillium Park – cozy up on the rocks with a blanket and a hot drink
Toronto Islands – fewer tourists, cooler temps, same epic views
8. Fall Theatre & Outdoor Performances
As the city cools, culture heats up:
Shakespeare in High Park runs through early September
Theatre season kicks off at Mirvish, Soulpepper, and Factory Theatre
Watch for Nuit Blanche in early October—a full night of city-wide art installations and immersive experiences
9. Cozy Up at a Café Patio
Patio season doesn’t have to end when the air turns crisp. Toronto’s café scene makes it easy to transition to sweater weather:
Balzac’s Distillery for rustic-chic autumn vibes
Boxcar Social (Harbourfront) for lake views and local sips
Sam James Coffee Bar or Pilot for indie charm with a side of people-watching
Wrap-Up:
Don’t let the season pass you by. Late summer and early autumn in Toronto are all about transition—sunshine by day, sweater weather by night, and endless things to do in between. Whether you're chasing that last cone of gelato or lining up for your first PSL, the city’s got you covered.
