May 22nd-31st Scotiabank CONTACT Festival @ various locations. The largest photography event in the world, featuring over 200 exhibitions and happenings throughout the GTA during the month of May. Throughout the festival, Canadians can also submit their own photos using #ScotiaGallery and they will be projected in various outdoor locations across Toronto.
May 23rd-June 2nd Inside Out Film Festival @ TIFF Bell Lightbox, 350 King St. W. Inside Out exists to challenge attitudes and change lives through the promotion, production, and exhibition of queer film. Full list of films here.
May 24th-25th Toronto Blue Jays’ Country Do Si Do @ Rogers Centre, 1 Blue Jays Way. Join the Toronto Blue Jays for their first two-day County Do Si Do. Fans can kick the dust up all weekend long with live pregame performances by Paul Brandt on Friday and Hunter Brothers on Saturday, plus line dancing and western-inspired activities. Tickets available online.
May 24th-June 2nd ReelAbilities Film Festival @ various locations. ReelAbilities Film Festival returns for its fourth year to showcase Canadian and International shorts, features, and documentaries about Deaf and disability cultures and by filmmakers and actors with disabilities and/or who are Deaf.
May 24th-June 2nd Eid Market @ Scarborough Town Centre, 300 Borough Dr. Eid Market is a celebration of Ramadan and Eid featuring 20+ vendors who will be selling everything from succulent treats to all-natural beauty products.
May 25th-26th Doors Open Toronto @ various locations. Doors Open Toronto returns to showcase some of the most architecturally, historically, culturally and socially significant buildings across the city. This year’s theme, 20 Something, will celebrate the first 20 years of Doors Open Toronto while looking forward to the next 20 years. Full list of participating buildings, special programs, and walking tours here.
May 25th-26th Woofstock @ Woodbine Park, 1695 Queen St. E. North America’s largest festival for dogs is turning 16! Woofstock is a canine celebration like no other: Shopping, games, entertainment, competitions, and all the doggie love you can imagine. Runs 10-5 pm both days.
10 am All That Glittered: Pop Culture in the 1970s @ Hot Docs Ted Rogers Cinema 506 Bloor St. W. Led by Geoff Pevere, All That Glittered is a six-part rollercoaster ride through the decade, exploring movies, fashion, music, TV, and politics. It will stare straight into some of the weirdest and most tasteless emanations of the day, but it will also look past them into what was really going on: what people were thinking, what they feared and desired, how they felt about the future and the past. Tickets are $63 for the six-week course (runs every Wednesday through June 19) or $21 for a single class.
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 hosts Megan Griffith-Greene and Jeromy Lloyd fire off questions ranging from sporting records and celebrity scandals to geographic discoveries and culinary lingo. $2 to participate. Email firstname.lastname@example.org or show up early to reserve a spot.
8 pm Trivia Night @ The Broadview Hotel, 106 Broadview Ave. Assemble your brain trust and head to the Broadview Hotel roof for Trivia Night! $5 per team to play, prizes to be won.
10 pm Higher Ground @ Bambi’s, 1265 Dundas St. W. Besides being one of the most respected radio shows of all that is funky and soulful (from the past to the future), Jason Palma’s Higher Ground had a long Wednesday night run at the original Octapus Lounge around the late ’90s. It was a mid-week institution that bridged the scenes between jazz, rare grooves, house, broken beat, hip-hop, drum ’n bass, and more. Join Palma and Basic Soul Unit as they bring it back for one night.
7 pm Friday Night Live: Let’s Dance @ Royal Ontario Museum, 100 Queen’s Park. Get ready to dance the night away at #FNLROM and be inspired by dance styles around the world! $19.21 tickets available online; limited amount available at the door.
7:30 pm Fast in the 6 @ Nathan Phillips Square, 100 Queen St. W. Coinciding with Ramadan, Fast in the 6 returns for a third year to celebrate all things that make Toronto great – its diversity, unity, and prosperity! Celebrate the breaking of the fast with free food from Sobeys and Maple Lodge Farms, laugh with a comedy skit from Mo Amer, and enjoy performances by Canadian singer Andee, rapper Raz, and more.
9 pm Decades Dance Party @ Handlebar, 159 Augusta Ave. The dance party to end all dance parties! Here’s how it works: every hour is a new decade of music from the ’70s until today. Every hour is a new DJ. The top of every hour is a confetti-fuelled countdown into the next decade. (It’s kind of like 5 New Year’s Eve parties in one. Except it’s not New Year’s Eve.)
10 pm Boom Boom Boom: Video Dance Party @ The Gladstone Hotel, 1214 Queen St. W. Go back to simpler times and pay tribute to all your ’90s and early ’00s faves with a night of their best videos! Featuring DJ Sean Caff mixing music videos from Aqua, Ace of Base, Vengaboys, Spice Girls, S Club 7, *NSYNC, Backstreet Boys, Atomic Kitten, La Bouche, Prozzak, Sugar Jones, SNAP!, Black Box, Bizzare Inc, 2 Unlimited, Basement Jaxx, Sugarbabes, Love Inc., and more. $10 in advance, $15 at the door.
10 pm 80s + 90s @ Stones Place, 1255 Queen St. W. ’80s and ’90s pop, rock, and alternative tunes all night with DJ Blush. $5.
10 pm Gold Chain @ The Ossington, 61 Ossington Ave. DJs Aoki and Snack will have you dancing all night long to the best hip-hop of today and yesterday. You don’t wanna miss this display of supreme DJing – it’s the gold standard.
10 pm DJ Crunch Bandicut @ Swan Dive, 1631 Dundas St. W. Rock ‘n’ roll weirdness all damn night with DJ Crunch Bandicut.
10 pm Get Lucky @ Clinton’s, 693 Bloor St. W. All the top 40, pop, and hip-hop you can handle. Raise the bar and your cups to a wild Friday night! $10.
10 pm DJ Akwasi @ The Boat, 152-A Augusta Ave. DJ Akwasi spinning all things hip-hop, RnB, Motown, disco, old school, and new school. Free before 11 pm, $10 after.
10 pm Beam Me Up Disco @ The Drake Hotel, 1150 Queen St. W. Beam Me Up is a disco jam that celebrates the underrated and the obscure of funk, jazz, soul, boogie, rare groove, reggae, gospel, proto-house! It’s an evening of tuneful transcendence, supplied by residents Patchouli Brothers and Cyclist.
10 pm Disco Fridays @ The Piston, 937 Bloor St. W. Hear a delightful array of disco and its sub genres every Friday at The Piston. $10.
10:30 am AGO All Hours @ Art Gallery of Ontario, 317 Dundas St. W. All day. All ages. All in. Celebrating the first day of the AGO’s new pricing model and the public opening of Canada’s first Infinity Mirror Room, AGO All Hours offers something for everyone – from engaging and interactive special installations and art-making activities to artist projects, marquee performances, and more! Admission is $25 for single ticket purchasers or free for visitors 25 and under, annual pass holders, and members.
11 am Trinity Bellwoods 50th Anniversary Bed In @ Trinity Bellwoods Park, 790 Queen St. W. Celebrate the 50th Anniversary of the one-day Bed In of John Lennon and Yoko Ono at Toronto’s King Edward Hotel. Though John and Yoko are only two people of many who share this vision, this Bed In is here to welcome all people from all walks of life to share these intentions and to express creatively to inspire this mission towards world peace. Bring your blankets, pillows, picnics, art, and drums to a day of wonderful entertainment and sharing under the boughs of the parks beautiful trees. Until 7 pm.
12 pm Greenwood Stakes @ Woodbine Racetrack, 555 Rexdale Blvd. Kick off spring into high style with a fashion-forward adrenaline-pumping day at the races. Push the fashion envelope and come decked out in your best derby attire – bespoke seersucker suits, spring dresses, pastels and florals, royal wedding inspired hats, and fascinators – to compete in the Style Stakes Best Dressed competition for a chance to win a cash prize. Enjoy craft cocktails designed by some of Toronto’s top mixologists at the Cocktail Jockey Mixologist Showcase, a pop-up gallery featuring artworks by Toronto visual artists, live music, lawn games, delectable food, and more. Tickets start at $75 and can be purchased online.
7 pm FemmeFest @ Supermarket, 268 Augusta Ave. An evening for celebrating the divine femme energy in our local community, aimed at nurturing and offering exposure opportunities to Toronto artists. Featuring musical performances by RAGA, KARIS, Dalia Dargazli, Melody Chance, and Blue Mantra. Until 11 pm.
10 pm Last Night Out @ Super Wonder Gallery, 584 College St. An event for women, femme presenting, masc presenting, androgynous, trans, cis, two spirit, non-binary folk, and anyone who has felt the discomfort of the “Saturday night club crowd” no matter where they fall on the LGBTQS2A+ spectrum. Featuring guest performances, games, raffles, and a dance party! $12 in advance, $15 at the door.
10 pm Wild Wild Party @ Duffy’s Tavern, 1238 Bloor St. W. All-vinyl 45 RPM 1950s-60s rock ‘n’ soul dance party with DJ Derek B. Garage! RnB! Beat! Fuzz! Hipshakers! Free before 11 pm, $5 after.
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 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 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 Simple Minds. $5 before 11 pm, $10 after.
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 Silent Alarm: Bloc Party Dance Party @ Sneaky Dee’s, 431 College St. Sound the Silent Alarm! Sneaky Dee’s will be spinning all your Bloc Party essentials, plus a whole host of your other dancey retro-rock favourites. $5 advance tickets available online.
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! DJ Blush plays pop, rock, and soul from the ’50s, ’60s, and ’70s. $10.
10 pm Roll + Skank @ The Ossington, 61 Ossington Ave. DJ night with the hottest beats around. All the way from the UK, this is what you’ve been waiting for.
10 pm Up Late @ Swan Dive, 1631 Dundas St. W. Retro, classic pop, rock, and soul with DJ Watu.
10:30 pm Hey Girl Hey @ The Baby G, 1608 Dundas St. W. Queer dance party featuring DJ Orange Pekoe playing hip-hop and R&B from female and non-binary artists + the 12:30 floorshow starring May Queen Miss Moço and an unmissable performance by Australian rapper/saxophonist Jamarz On Marz. $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, enjoy the sunshine and brews while you shop local Ontario farmer stands and crafty booths. Until 2 pm.
10 am Gluten Free Garage @ Artscape Wychwood Barns, 601 Christie St. Toronto’s original pop-up gluten-free market celebrates its eighth year! Featuring 65+ vendors, guest speakers, food demos, food trucks, libations, and samples. Until 4 pm. $10 advance tickets available online.
10 am The Trinity Bellwoods Flea @ The Great Hall (lower level), 1087 Queen St. W. The Trinity Bellwoods Flea returns with a top-notch selection of local vendors, artisans, and delicious eats. Four-legged friends welcome! Until 5 pm.
10 am GH Marketplace: Legends Vintage @ The Gladstone Hotel, 1214 Queen St. W. Vintage fashion specialist Andrea Lalonde invites style-forward vendors to deliver a dream shopping experience. This marketplace is aimed at emerging and seasoned vintage collectors and anyone serious about expressing their personal style through unique fashion pieces. Until 6 pm.
12 pm Garrison Spring Flea @ The Garrison, 1197 Dundas St. W. The Garrison and Black Diamond Vintage are teaming up again for another marketplace! Bringing you the city’s finest in vintage and independent makers. Until 6 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 10 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.” This edition features performances by Charlie Quinn, Gigi Marx (MTL), Lucy Buttons (NYC), and Weird Alice Yankadic (Melbourne). Free entry; tipping encouraged.
~ For event submissions, email Caitlyn Holroyd at email@example.com