Things to Do in Toronto This Weekend: October 23-25, 2026

Looking for things to do in Toronto this weekend? The last full weekend of October brings a ski and snowboard show, a costume afternoon for dogs, a community parade and a car-free street festival. Three of the four are free or pay-what-you-can. Here is what is on from Friday, October 23 to Sunday, October 25, 2026, with the practical details worth knowing before you go.

The Toronto Ski + Snowboard Show (Friday to Sunday)

If the first cold snap has you thinking about winter, this is your stop. The Toronto Ski + Snowboard Show runs Friday, October 23 to Sunday, October 25 at The Better Living Centre, 195 Princes' Boulevard at Exhibition Place. Tickets are listed at $18 to $24 plus fees.

The show is aimed at everyone from first-timers who want to learn to ski or snowboard, to experienced riders looking for new gear, winter travel ideas and deals from retail exhibitors. It is a good plan for a family that wants to get ready for the season in one afternoon.

Howl'oween at The Bentway (Saturday)

On Saturday, October 24, Howl'oween at The Bentway brings a dog-focused afternoon to 250 Fort York Boulevard. Expect creative costumes, prizes for the pups and pet-focused local vendors. It is free to attend, and you do not need a dog to enjoy the people-watching.

Night of Dread Parade (Saturday)

On Saturday, October 24 from 5 to 8:30 pm, Clay & Paper Theatre presents its annual Night of Dread at Dufferin Grove Park, 875 Dufferin Street. It is a much-loved, family-friendly community event built around parade, puppetry, music and masquerade.

Here is how the evening unfolds:

• 5 pm: live music and a participatory warm-up dance on the basketball court, followed by an opening performance from the Magpie Club, the company's youth stilt-walking ensemble.
• The pageant: the "Fear of the Year" for 2026 is announced and confronted.
• After the pageant: a concert in the Forest of Remembrance, then a bonfire where the Fire Keeper names and burns the community's fears.

Want to be part of the procession? Puppet sign-out runs from 3:30 to 5:30 pm at Puppet Central in the Dufferin Grove Rinkhouse. Participation is pay-what-you-can, with $25 suggested, and donations go to support the artists. 

Pedestrian Sundays in Kensington Market (Sunday)

On Sunday, October 25 from 12 to 7 pm, Pedestrian Sundays closes the streets of Kensington Market to cars for the 19th year. It is free, and the listing describes plenty of food, poetry and dance, plus the Kensington Market Art Fair, a curated outdoor show of two and three dimensional art, and a community yard sale.

Plan your route before you go. Road closures run from 11:30 am to 7:30 pm on Augusta Avenue from Oxford Street to College Street, and on Kensington Avenue from Baldwin Street to Dundas Street West. Oxford Street, Nassau Street and Wales Avenue have partial closures for local traffic only. Cars still parked on the closed streets after 11 am are towed, so transit or a parking spot outside the zone is the easier choice.

Use the weekend to get to know a neighbourhood

A busy weekend is also an easy way to explore parts of Toronto and surrounding areas without any pressure. These four events take you to Exhibition Place, Fort York, Dufferin Grove and Kensington Market, and each one shows you something a listing photo cannot: how far the park is from the street, how easy it is to get there on transit, and what the area feels like when it is busy.

If you are thinking of buying: pick one area you are curious about, and notice what you would use every week. Parks, transit, local shops and noise levels matter more to daily life than most people expect. Then return on an ordinary weekday to see the quieter side.

If you own a home nearby: big community events are a good reminder of what makes your area appealing to others. Buyers often ask about the things around the home, not only the home itself.

My take: I like events that bring people into the neighbourhood on foot. If you are curious about a part of the city you visit this weekend, I am happy to share what I know about the area. No pressure at all, and I'm here for you whenever you are ready to talk.

👩🏻‍💼 Khoa Le, Real Estate Broker | Real Broker Ontario
📱 647-271-5461
📧 khoa@realimpactgroup.com
🏡 @realimpactgroup | @realbrokerage 

This post shares general information about local events and is not legal, tax or mortgage advice. Event details can change, so please check each organizer's page before you go.

Sources: To Do Canada: Things to Do in Toronto This Weekend