September 26th-28th Toronto Oktoberfest @ Ontario Place, 955 Lakeshore Blvd. W. Food, beer, music, and a fun fair modelled after the original Munich event! Join thousands of others dressed in lederhosen and dirndls under a massive Bavarian-style Festhalle tent in celebration of German culture. $20+ tickets available online.
September 26th-October 5th 29Rooms @ Queen Elizabeth Building (Exhibition Place), 100 Princes’ Blvd. Refinery29 is bringing its immersive pop-up event 29Rooms to Toronto for the first time! The 29Rooms: Expand Your Reality experience will create new, bold, and thought-provoking moments that bring Refinery29’s mission and multi-sensory spaces to life in collaboration with global artists, creators, visionaries, meaningful causes, and brands. Tickets start at $30.
September 27th-28th INLAND @ QRC West, 134 Peter St. Canada’s leading pop-up destination to shop contemporary fashion, apparel, and accessories. Bringing together a curated mix of exclusively Canadian brands, INLAND is a future-focused shopping experience that values people, the planet, and personal style in equal measure. Runs 3-9 pm Friday and 11-7 pm Saturday.
September 27th-October 27th Halloween Haunt @ Canada’s Wonderland. Face your fears when darkness falls as Canada’s Wonderland is transformed from a “theme park” into a “scream park” during Halloween Haunt. Experience the thrills of your favourite rides at night and the frights awaiting you in our terrifying haunted attractions and shows. $31.99 tickets available online.
September 27th-October 31st Legends of Horror @ Casa Loma, 1 Austin Terrace. An immersive theatrical interpretation of all of the classic horror figures. Audiences are led through a one hour, 2 km self-guided walking tour commencing in the lower gardens of Casa Loma and winding its way through the castles tunnels and darkest spaces never before open to the public. $42.83 tickets available online.
September 28th-29th Toronto Vintage Clothing Store @ Enercare Centre (Exhibition Place), 100 Princes’ Blvd. Canada’s largest sale of vintage clothing, jewelry, handbags, accessories, menswear, designer, and more! Runs 10-5 pm Saturday and 10-4 pm Sunday. $12.
September 28th-29th Toronto Antique & Vintage Market @ Enercare Centre (Exhibition Place), 100 Princes’ Blvd. Whether you’re on the hunt for vinyl records, typewriters, mid-century modern wares, or cool bohemian-style furnishings, you’re sure to find it at the Toronto Antique & Vintage Market. Runs 10-5 pm Saturday and 10-4 pm Sunday. $12.
7 pm Music Bingo @ The Gladstone Hotel, 1214 Queen St. W. A FREE weekly event combining the love of music with the traditional bingo format. Each player receives a Music Bingo card which consists of an assortment of songs. Instead of calling out numbers, they play the music! Singing along encouraged.
8 pm Drake Trivia @ The Drake Hotel, 1150 Queen St. W. Teams of four or less put their random knowledge to the test as the hosts fire off questions ranging from sporting records and celebrity scandals to geographic discoveries and culinary lingo. $2 to participate. Email email@example.com or show up early to reserve a spot.
6:30 pm We Really Like Her: Crossroads with Britney Karaoke Pre-Show @ Revue Cinema, 400 Roncesvalles Ave. The MUFF Society and We Really Like Her present a Britney-only karaoke party followed by a screening of the 2002 film Crossroads, starring Britney Spears, Zoe Saldana, and Taryn Manning. Singalongs during the film are encouraged. $12-14 tickets available online. Karaoke at 7 pm, film at 7:30.
7 pm Drunken TV: Beverly Hills, 90210 @ The Gladstone Hotel, 1214 Queen St. W. An interactive TV viewing party game mini-series based off the ’90s series Beverly Hills, 90210! The theme for this edition is “Parties Gone Wrong.” There will be customized game cards, props, colouring book pages, and themed cocktails for 90210 fans. Space is first come, first serve, so make sure to arrive early (starts promptly at 7:30 pm).
7 pm SiriusXM Top Comic Finale @ Queen Elizabeth Theatre, 190 Princes’ Blvd. Hosted by Ben Miner, the SiriusXM Top Comic Finale will see 10 of Canada’s funniest comedians go mic-to-mic for a $25,000 prize as part of JFL42. This year’s finalists are Drew Behm, Sophie Buddle, Adam Christie, Ola Dada, Courtney Gilmour, Nigel Grinstead, Andrea Jin, Jess Salomon, Kelly Taylor, and Alex Wood. $39.50 tickets available online.
10 pm Fuzzed & Buzzed @ Swan Dive, 1631 Dundas St. W. Get buzzed and enjoy some fuzzed-out rock ‘n’ roll tunes hand-picked by the Fuzzed & Buzzed crew!
9 pm Knockout! @ Handlebar, 159 Augusta Ave. Knockout welcomes Brad and Jon Francois from Peoples Records in Detroit for this edition. From the needle drop to the very end, you can expect the best of rare soul, funk, and reggae to heat up the dance floor!
10 pm Jamz @ Clinton’s, 693 Bloor St. W. DJs Slater and Ty mashin’ heavy tunes from the ’90s to the ’00s, including DMX, J-Lo, Britney, Ludacris, Missy, Spice Girls, Mariah, Backstreet Boys, Ashanti, Destiny’s Child, and more. $10.
10 pm DJ Teenage Werewolf @ Swan Dive, 1631 Dundas St. W. Friday night freak out with DJ Teenage Werewolf playing rock ‘n’ roll, soul, psych, and punk.
10 pm Eighties + Nineties @ Stones Place, 1255 Queen St. W. Nothing but rock, pop, dance, and hip-hop from the ’80s and ’90s with DJ Blush. $5.
10 pm Wax Candy Disco Party @ The Piston, 937 Bloor St. W. DJ Efsharp and Cyclist serve up platters of the sweetest soulful, refreshing, and uplifting disco in one of the best sounding rooms in the city. $10.
11 pm Get Good @ The Drake Underground, 1150 Queen St. W. Diggy The DJ plays all your favourite bangers. $10.
10 am Etsy: Made in Canada Toronto @ MaRS Discovery District, 101 College St. The sixth annual Etsy: Made in Canada Toronto, hosted by the Toronto Etsy Street Team and 416Hustler! Featuring more than 130 of the best local artists and hand-makers selling their wares + crafty workshops, a raffle, and more. Until 6 pm.
1:30 pm Throwback Cinema: Harriet the Spy @ The Revue Cinema,400 Roncesvalles Ave. Calling all spies! Get out your red sneakers, yellow rain jackets, and very PRIVATE spying notebooks, for Throwback Cinema cordially invites you to a super secret screening of 1996’s Harriet the Spy. $11-14 tickets available online.
5 pm Sunnyside 21: Season Finale @ Sunnyside Pavilion & Cafe, 1755 Lake Shore Blvd. W. Sunnyside wraps up its 21st season of summer music events under the sun, moon, and stars! The final installment will feature Art Department, Kenny Glasgow, and Rudee NikIberican. $43.11-49.10 advance tickets available online.
10 pm Juicebox @ The Piston, 937 Bloor St. W. DJs Babs and Jorge spinning the indie, retro, and Britpop you need! You will hear: The Strokes, David Bowie, Pulp, The Stooges, LCD Soundsystem, Bloc Party, The Human League, Joy Division, Holy Ghost, Glass Candy, and lots more! $10.
10 pm Saturday Night Jukebox Dance Party @ Stones Place, 1255 Queen St. W. Sweat it out to the sweet sounds of the golden age of rock ‘n’ roll and soul music. Special guest DJ Junkyard Jesse (No Warning/Headstones) plays pop, rock, and soul from the ’50s, ’60s, and ’70s. $10.
10 pm Mad Fun @ Swan Dive, 1631 Dundas St. W. Mad fun all night long with DJ Fawn Big Canoe! Classic disco, soul, pop, and rock.
10 pm Wedding Party @ The Boat, 152-A Augusta Ave. Everyone is the bride at Wedding Party! Playing the golden hits for any and all to groove to – soul, funk, new wave, and hip-hop.
10 pm Worst Behavior @ Clinton’s, 693 Bloor St. W. This Saturday, be on your worst behavior. Bangs & Blush play past and present bangers all night long from Drake, The Weeknd, Beyoncé, Jay-Z, Notorious B.I.G., Nelly, TLC, Missy Elliott, and more! $10.
10 pm Panic @ Remix, 1305 Dundas St. W. The ultimate retro party with DJ Lazarus spinning the kind of retro that changed your life. ’80s, ’90s, new wave, post-punk, classic alternatives, synth pioneers, Britpop, shoegaze, madchester, new romantic, classic industrial, ska, and more. This month’s spotlight is OMD. $5 before 11 pm, $10 after.
10 pm DJ Moe Funk @ Farside, 600 Gerrard St. E. DJ Moe Funk plays strictly vinyl funk, soul, old skool, jazz, and other treats.
11 pm DJ Classy + DJ Graveyard Rock Ultra Boogaloo @ The Garrison, 1197 Dundas St. W. DJs Classy and Graveyard Rock take over The Garrison’s front room for a 7” record riot, spinning garage, punk, glam, and soul jammers until 4 am.
11 pm Hey Girl Hey @ The Baby G, 1608 Dundas St. W. Queer dance party featuring DJ Orange Pekoe playing the sweetest hip-hop & RnB bops by female/non-binary artists + Beardoncé paying tribute to one of the most iconic hip-hop albums of all time, The Miseducation of Lauryn Hill. $10.
11 pm Itzsoweezee @ The Drake Underground, 1150 Queen St. W. Itzsoweezee is a counterculture brand whose values are built on a way of life and set of attitudes that substantially differ from social norms. They cater to lovers of floor-filling hip-hop, house, and electronic music. $10.
9 am Sunnyside Sunday Market @ Great Lakes Brewery, 30 Queen Elizabeth Blvd. A new farmers market is coming to Etobicoke this summer! Each Sunday through September 29th, enjoy the sunshine and brews while you shop local Ontario farmer stands and crafty booths. Until 2 pm.
11 am OCAD Artist Alley @ The Great Hall (second floor), 100 McCaul St. Need new paintings or ceramics to decorate your room? Maybe a one-of-a-kind jacket, or a custom ring? Some prints, zines, or stickers? Stop by OCAD’s first student-run Artist Alley and support 50+ student artists and alumni. Bring cash, as most artists do not have card readers. Until 7 pm.
12 pm Pedestrian Sundays @ Kensington Market. Toronto’s favourite neighbourhood festival celebrating Kensington Market and its vibrant community of businesses, artists, and people is back! The streets are yours until 7 pm.
7 pm Brass Facts Trivia @ The Ossington, 61 Ossington Ave. Test your knowledge and win prizes! Hosted by Famous Kirk Hero. Until 10 pm.
10 pm Sinful Sundays Burlesque @ Cherry Cola’s, 200 Bathurst St. Come be entertained at this weekly “temple of tease,” where you’ll find a fresh lineup of burlesque entertainers, drag, and variety acts. Free entry; tipping encouraged.
~ For event submissions, email Caitlyn Holroyd at firstname.lastname@example.org