Here comes another glorious weekend, Toronto! We’re halfway through September and the weather is still as gorgeous as ever. Aren’t we lucky? As for what’s new and exciting in the city this weekend, we have good news for you. Some of the best fall festivities and pumpkin events are officially opening up for the season, but if you’re not ready to part with summertime fun, you’ve got boat parties and music festivals to attend. Whatever you choose to do, now’s the time to bask in the sunshine while we still have it.

Without further delay, here are 10 of the best things to do in Toronto this weekend.


A fall festival you won’t want to miss. In addition to the iconic “sea” of 10,000 pumpkins on display at this event, Downey’s Farm will have a corn maze, farm animals, wagon rides, live entertainment, jumping pillows, a skeleton band, and more, so you can load up on everything you love during Ontario’s prettiest season. Downeys’ pumpkin donuts are made fresh on-site and they even have pumpkin donut ice cream sandwiches, so be sure to bring your appetite.

Where: 13682 Heart Lake Rd
When: September 18th—October 31st


Drive your way through an enchanting tunnel filled with thousands of glowing jack-o-lanterns. These pumpkins are hand-carved and there are live carving demonstrations so you can see how the pros create their masterpieces. If you want to get a head start on your Halloween bucket list, this award-winning annual tradition is a must!

Where: Country Heritage Park, 8560 Tremaine Rd
When: September 17th to November 7th


There’s no better way to enjoy summer in the 6ix than a nighttime cruise with skyline views. The boat is equipped with 3 full-service bars, live DJs, snacks for sale, and a club-like dancefloor. The event is 4 hours, rain or shine, so dress for the weather!

Where: 11 Polson St
When: September 18th & 19th


Rock out to a live show from Ontario’s very own indie-pop band, Walk Off The Earth. The season of outdoor concerts at Budweiser Stage is almost over, so don’t miss your chance to enjoy it to the fullest!

Where: Budweiser Stage
When: September 18, 2021

TIFF 2021

The stars are in town for the last few days of the Toronto International Film Festival. This year’s TIFF is a combination of virtual and in-person screenings at theatres around the city, and you’ve got so many highly-anticipated films to see. Don’t miss them while they’re still here!

Where: Various locations
When: Until Saturday, September 18th


Check out this complimentary exhibit at the Royal Ontario Museum this month and reflect back on our pandemic experience in a unique way. The exhibit is called Unmasking the Pandemic: From Personal Protection to Personal Expression — it showcases 60 original facemasks, each with its own backstory and symbols that reflect the struggles we’ve all experienced in some way, both together and apart.

Where: 100 Queens Park
When: Opens September 18th, 2021


Festival season is still going here in Toronto and there’s a good one coming up this Sunday at the CityView Drive-in. Tickets to the 19+ event are extremely limited capacity but there are still some for sale. You’ll get to dance to the live sounds of so many artists, including Addy, Dee Cee b2b Quim, Flip Side, Jay Force, and more. It’s not over ’til it’s over, so let’s make it count.

Where: 20 Polson St
When: Sunday, September 19th

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Make your way just outside of the city to this celebration of beer and cider from over 35 Ontario craft brewers. The event will feature live music, gourmet food, and a charming countryside atmosphere. Tickets are no longer available for purchase online, but you may be able to get one at the main entrance for $45 each. Plus, all the proceeds will be donated to local charities.

Where: 11494 Trafalgar Rd
When: Saturday, September 18th


We may be approaching the end of the season, but it’s not too late to enjoy Ontario’s quintessential summer activity — winery tours! The best part is that you don’t even have to drive to wine country yourself. Your ticket comes with round-trip transportation from Toronto’s Union Station Bus Terminal to your choice of two wineries in the Niagara region. Once you arrive, you’ll get to enjoy a 2-hour wine and food pairing, with a pit stop at the Wine Rack on your way home.

Where: 81 Bay St
When: Saturday, September 18th & Saturday, September 24th


Wander through this 10-acre corn maze just north of Toronto at Cooper’s Farm, which you can explore with a flashlight at nighttime for some extra thrills. There’s a lot of fall fun to be had at this cute spot. Bonus, you can even bring your dog on Saturdays!

Where: 266 Ashworth Rd, Zephyr, Ontario
When: Opens September 18th, 2021

Cheers to the weekend, Toronto!