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26 of the best things to do in Toronto this September

Via WLSN SZTO/ Ded Agency

Anyone else not see September coming?! We’re getting surprise slapped in the face by fall here. Summer has come and just about gone, which means we’re officially out here gearing up for autumn and getting back to the PSL grind. And as we all know, leaves changing means we need a wardrobe change to go with it. We teamed up with our friends at Little Burgundy to bring you the must-have shoes for fall that happen to pair perfectly with all the awesome things happening in Toronto this month!

Here are 26 wicked things to do in Toronto this September!

TORONTO INTERNATIONAL BUSKER FEST

This festival is a massive showcase of world-class performers. Music, acting, dancing, juggling massive swords… it’s all here, pals. Look your coolest but stay comfy in these Oxford boots!

When: Sunday, September 1- Monday, September 2
Where: Woodbine Park, 1695 Queen St E
Cost: Admission by donation to Epilespy Toronto

ONE LOVE FESTIVAL

Our one love, besides our fanny pack, is going to festivals. Specifically Caribbean ones, because we can eat so much food, jam to so much music, and fit so much in our fanny packs!

When: Sunday, September 1- Monday, September 2
Where: Downsview Park, 70 Canuck Ave, North York
Cost: $20

RIB, BACON, AND BBQ FEST

We like to challenge ourselves: how many ribs can we eat? How long will our super cute white sneakers stay white at this event? Time to find out, pals.

When: Sunday, September 1- Monday, September 2
Where: Downsview Park, 70 Canuck Ave, North York
Time: Sunday 11 AM- 11 PM, Monday 11 AM- 8 PM
Cost: Free- $8

ELECTRIC ISLAND CONCERT AND PICNIC SERIES

Electrify your summer one last time at this wicked music festival in the park. We hear this neat Adidas waist bag not only holds your essentials, but also prevents electrocution. Seems like a good pick.

When: Sunday, September 1
Where: Hanlan’s Point, Toronto Islands
Time: 2 PM- 10:30 PM
Cost: $57.74

CANADIAN NATIONAL EXHIBITION

Squeeze the last bit of CNE excitement out this weekend, kinda like when you’re making lemonade but you’re a lemon short. Just don’t wanna let it go. These cute sneaks will make one last trip to The Ex the perfect ending.

When: Runs until Monday, September 2
Where: 210 Princes’ Blvd
Cost: General admission $19.99

LENNY KRAVITZ

We wouldn’t tell you to wear some janky flip flops to Lenny. No siree. Go get serenaded in these black Talib boots and maybe he’ll notice you!

When: Wednesday, September 4
Where: Budweiser Stage, 909 Lake Shore Blvd W
Time: 8 PM
Cost: Find tickets here

LUKE BRYAN

So you wanna be juuuust a little country, but without sacrificing your style? We get it. Get that leather look fit for Luke but in some kicks you’ll want to wear again and again. Thanks, Matt and Nat.

When: Thursday, September 5
Where: Budweiser Stage, 909 Lake Shore Blvd W
Time: 7 PM
Cost: Find tickets here

TORONTO INTERNATIONAL FILM FESTIVAL

Catch screenings, spot stars, and then sneak your way onto the red carpet! In boots this classy, it’ll be a while before they realize you’re not supposed to be there.

When: Thursday, September 5- Sunday, September 15
Where: TIFF Bell Lightbox, 350 King St W
Cost: Varies, buy tickets here

TORONTO DRAGON FESTIVAL

Thinking of spending this festival eating Chinese food, watching performances, and admiring those dudes in the giant dragon costume? We’re so in. We’re also in these classic suede Vans. Think they come in dragon colour?

When: Friday, September 6- Sunday, September 8
Where: Nathan Phillips Square, 100 Queen St W
Cost: Free

TORONTO VEG FEST

You love the Earth, you love animals, and you love your vegan mini backpack. It’s a cute bag, and it’ll earn you major points at Veg Fest for being partially made of recycled water bottles. More veggie tacos, stat!

When: Friday, September 6- Sunday, September 8
Where: Harbourfront Centre, 235 Queens Quay W
Cost: Free

CABBAGETOWN FESTIVAL

If Toronto does anything well, it’s the neighbourhood street festival. We’re pretending to be from Cabbagetown for the day, wanna join? We’ve got snacks packed in this wicked Nike backpack, but there’s room for more.

When: Saturday, September 7 & Sunday, September 8
Where: Parliament St from Wellesley to Gerrard, and Carlton St from Ontario to Parliament
Cost: Free admission

KACEY MUSGRAVES

Hot take: Musgraves sounds a bit too much like muskrat. Still good tho. Another hot take: we’d rather wear these chunky heeled boots than anything Western. Wanna join?

When: Monday, September 9
Where: Sony Centre for the Performing Arts, 1 Front St E
Time: 8 PM
Cost: Find tickets here

MARY J. BLIGE & NAS

Wanna go to this show together? Fine, we’ll oblige. Snag tickets and snag these sick Fila sneakers. You’ll be in Real Love with them. Yeah, that was a couple of weak jokes. Laugh anyway please.

When: Tuesday, September 10
Where: Budweiser Stage, 909 Lake Shore Blvd E
Time: 8 PM
Cost: Find tickets here

OF MONSTERS AND MEN

Let’s get into our Icelandic chill indie vibes together. Let’s also get into these classic black Vans because your Dirty Paws deserve only the best!

When: Wednesday, September 11
Where: Budweiser Stage, 909 LakeShore Blvd W
Time: 8 PM
Cost: Find tickets here

BRAMPTON FALL FAIR

We know, we know. You don’t want to hear the word “fall” yet. It’s okay, this festival is going to remind you that there’s good things about the season, like food and family and friends. And mustard yellow coming back into the fashion palette, which we’re way too excited about.

When: Thursday, September 12- Sunday, September 15
Where: Brampton Fairgrounds, 12942 Lake Rd, Caledon
Cost: Free admission

TORONTO BEER WEEK

If you’re getting brushed up on your craft beer knowledge, you better be doing it in style. Stroll up to breweries aplenty in these Lucas Cow Suede boots so you can look the part while you appreciate the brews.

When: Friday, September 13- Sunday, September 22
Where: Throughout Toronto

OKTOBERFEST AT CANADA’S WONDERLAND

Beer and autumn celebrations with rollercoasters and a lil’ sprinkle of German fun? You just described an ideal time for us. Make the most of the day with the essentials tucked safely away in this Nike Tech Bag, so you can double fist to your heart’s content!

When: Saturday, September 14
Where: Canada’s Wonderland, 1 Canada’s Wonderland Dr, Vaughan
Time: Starts at 11 AM
Cost: Regular admission

CANNED CRAFT BEER FESTIVAL

Craft beer folk tend to look cool while doing anything, and we want to be one of them. Doc Martens and an IPA in hand? We’re really starting to look the part here. Also, we’re really into this beer.

When: Wednesday, September 18
Where: Duke of Somerset, 655 Bay St
Time: 5 PM- 7 PM
Cost: $8

JFL42

No, we didn’t just throw some letters and numbers in there. It’s Just For Laughs’ massive comedy fest! Slip into these adorable heeled booties while we try and illegally slip onstage to get some laughs. We’re the next big stand-up thing, promise!

When: Thursday, September 19- Sunday, September 22
Where: Sony Centre for the Performing Arts, 1 Front St E
Cost: Starts at $29.50

FRANCOPHONIE EN FETE FREE CONCERT WEEKEND

We don’t sprechen ze French. Wait, that wasn’t right… We still appreciate a good bop though! If you’re into music, this is for you. If you’re into music and speak French, this is SO for you! Who doesn’t love free concerts? We’ll be tucking a small French-Enlighs dictionary into our crossbody purse du jour.

When: Friday, September 20- Sunday, September 22
Where: Distillery District
Cost: Free

FIRST NHL PRESEASON GAME

What the heck, it’s already hockey season? Time flies when you’re desperately waiting for the LEafs to win the cup. Get in the team spirit from head to toe in these perfectly coloured and perfectly cool Air Maxes. Maybe this is the year…

When: Wednesday, September 25
Where: Scotiabank Arena, 40 Bay St
Time: 7 PM
Cost: Find tickets here

HARVEST FESTIVAL

We’re going to the country, so you’d better slip the Blundstones on. We’re still going to be Instagramming every cute fall thing though, so you’d better slip the heeled Chelsea Blundstones on! You look so pumpkin spice, ya little cutie.

When: Saturday, September 28
Where: 1219 Nurloak Dr, Oakville
Time: 10 AM- 4 PM
Cost: Daily vehicle permit required

CANNABIS LIVING EXPO

Cannabis is a lifestyle, mom! Gosh! At least she can’t fight you on these green Sid DX Vans sneakers, because they’re so fresh. And so green. Little Burgundy knows what’s up!

When: Saturday, September 28 & Sunday, September 29
Where: 6900 Airport Rd, Mississauga
Cost: Day passes $20, weekend passes $35

COUCH FILM FESTIVAL

We like to loaf around. Also, we like to enjoy our film festivals in the fully loafed position, so this one’s a favourite of ours! If you decide to get up from the couch, do it in these stylish loafers. Or just loaf in them, which is totally cool too.

When: Monday, September 30
Where: The Burroughes Building, 639 Queen St W
Time: 6 PM- 9 PM
Cost: Free

YOUNG THUG/MACHINE GUN KELLY

We used to rock classic black Chucks when we were a yung thug. Nothing’s really changed, except now Machine Gun Kelly is in Toronto and we’re rocking the Chucks (and thugging as per usual) in the crowd.

When: Monday, September 30
Where: Echo Beach, 909 Lake Shore Blvd W
Time: 7:00 PM
Cost: Find tickets here

We’re going to be riding this wave of 24 degree days as far into fall as it’ll last. At least these awesome things to do in Toronto this September will ease the transition, right?

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