23 Fun Date Ideas in Toronto for Fall 2019

It’s sweater season! The leaves are changing and so should your dates. If you’re looking to switch up your regular routine of strolling around the park with your furry friend and drinking pumpkin spice lattes at your local coffee shop, add some of these fall 2019 date ideas in Toronto. From film festivals to outdoor activities and everything in between, we’ve got something for everyone.

Here are our favourite fall date ideas in Toronto.

Fall events and festivals

Mark your calendars with these events and festivals that make for some of the best date ideas in Toronto for fall 2019.

Celebrate Oktoberfest

Get your lederhosen and dirndls on and go to Toronto Oktoberfest to party under a massive Bavarian-style Festhalle tent (September 26 to 28)

Cirque du Soleil

Cirque du Soleil’s ALEGRIA is in town under the Big Top at Ontario Place. (September 12 to November 24) 

Get spooked at a Halloween Haunt

Canada’s Wonderland will be transformed from a theme park into a scream park. Facing your fears will be a lot easier with your S.O. in tow. Halloween Haunt runs select nights September 27 to October 27.

The Rocky Horror Show

Catch a live performance of The Rocky Horror Show at Hart House Theatre (September 17 to Oct 12)

Nuit Blanche

Wander the streets of Toronto from dusk to dawn to see Nuit Blanche installations and exhibits. Toronto will be transformed by hundreds of artists and nearly 90 art projects.(October 5, 7 pm to 7 am)

Toronto After Dark Film Festival

Watch the best new horror, sci-fi and action movies from around the world at the Toronto After Dark Film Festival at Cineplex Scotiabank Theatre (October 17 – 25)


The imagineNATIVE Film and Media Arts Festival is the world’s largest festival showcasing film, video, audio, and digital + interactive media made by Indigenous screen-content creators. Events will be held at various venues in Toronto (October 22-27)

Beaches Studio Tour

Go to the Fall 2019 Beach Studio Tour to visit artists’work spaces and view art and design (October 25-27)

80s Tribute Halloween Party

Get your neon on and rock an 80s costume – tees, hats, bangles, sweat bands, leg warmers – and head to the Revival Bar for The Breakfast Club 80s Tribute Halloween Party (October 25)

Fun things to do

You’ll want to get outside to enjoy the fall colours and the harvest with these fun date ideas.

Make a feast

Hit up a Toronto farmers market then use your goodies to make dinner together.

Drive to the country

Go apple picking and get lost in a corn maze. It’s not just for kids, I promise!

Visit a fall fair

Don’t forget to make out on the ferris wheel.

Decorate your place for Halloween

Time to try out some of those Pinterest crafts you’ve been saving.

Bid farewell to patio season

Go to a romantic restaurant and snag a table outdoors. You need to enjoy the good weather while it lasts!

Go back to school! 

Just because you’re adults doesn’t mean you can’t try new things. Take a pottery, cycle or cooking class to learn a new skill together.

Host a block party 

Host your neighbours for a fabulous fall feast. Don’t forget to plan some fun and games.

Hit up a concert! 

Try seeing an artist you’ve never heard of, they may be the perfect surprise addition to your fall playlist.

Go to a drive-in movie

So much better than binge-watching a show for another night in a row.

Make Thanksgiving dinner

Nothing says “I love you” like figuring out how to roast a turkey together.

Go on a tasting tour

Tour your local breweries or wine bars, if you prefer chardonnays to IPAs.

Carve a pumpkin

Have a pumpkin carving face-off. Winner takes all.

Sport a couples Halloween costume

Whether you want to be Veronica and Archie or Zoolander and Hansel is your call.

Celebrate the beginning of hockey season

Go to a Leafs or Marlies game or hit up a sports bar like the The Rec Room.

Photo by Beth Teutschmann / Unsplash

Looking for more fall date ideas? Explore the best Toronto date ideas on Fluttr!

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