53 events and festivals to check out in Toronto this winter

Dec 16 2019, 5:19 pm

Believe it or not, winter is just getting started.

Starting December 21, and running until March 19, the coldest season of the year is bringing a whole fleet of great events and festivals with it.

Tunnel of Glam

What: The celebrated Tunnel of Glam returns for its second year. Members of the public can visit this outdoor, 80 ft. pedestrian tunnel lined with 14 million reversible sequins for a delightfully festive and immersive winter time destination.

When: Now until January 6
Where: 1501 Yonge Street
Admission: Free

A Nutcracker Christmas at the Castle

What: Toronto’s only castle will host a wide range of activities and thrilling performances that will be fun for the whole family. Enjoy new shows by famed illusionist entertainer Professor Wick and ice skating performers Glisse on Ice. Guests will be surrounded by holiday magic throughout the castle which will be resplendent with holiday décor,

When: Now until January 5
Time: Daily, December 1 to January 5, 9.30 am to 5 pm; nightly, December 15 to December 30, 5 pm to 9 pm
Where: Casa Loma — 1 Austin Terrace
Admission: $30, available online

Miracle on Ossington pop-up bar

What: All this Christmas cheer is probably going to make you want a cocktail. Start a new tradition by heading west to the Miracle on Ossingting pop-up. Sip on holiday-themed drinks while sitting warmly among with a huge amount of fun, kitschy holiday decorations.

When: Now until December 26
Time: Monday to Friday, 5 pm to 2 am; Saturday to Sunday, 2 pm to 2 am
Where: 146 Ossington Avenue

Sippin’ Santa

What: What’s better than one winter pop-up? Two holiday winter pop-ups, that’s what. Get your Christmas spirit with a Tiki twist that’s full of music, themed drinks

When: Now until December 26
Time: Monday to Friday, 5 pm to 2 am; Saturday to Sunday, 2 pm to 2 am
Where: 1369 Dundas Street West

Canada’s Wonderland WinterFest

What: Canada’s Wonderland is transforming the park into a magical winter wonderland for its new immersive, holiday event and it all kicks off this weekend. Winter festival goers will experience enchanting themed areas adorned with more than five million holiday lights, festive décor and three 15-metre-high Christmas trees. There will also be tons of music and Christmasy activities for everyone.

When: Now until December 31
Time: Times vary, check online
Where: Canada’s Wonderland — 1 Canada’s Wonderland Drive
Tickets: Start at $21.99, available online

Martin Scorsese: A Retrospective

What: He’s one of the globe’s greatest and most iconic of filmmakers. See 27 of the master’s feature movies, playing into the new year, and see what makes Marty one of the best.

When: Now until January 4
Time: Times vary, check online
Where: TIFF Bell Lightbox — 350 King Street West
Admission: Prices vary, available online

Aurora Winter Festival

What: For the first time ever, Aurora Winter Festival will transform Toronto’s Ontario Place into a hidden village with enchanting elements inspired by the North Pole including magical characters, captivating light displays, endless fun, games, and activities.

When: Now until January 5
Time: 4 pm to 10 pm
Where: Ontario Place, 955 Lake Shore Boulevard West
Price: $17.99, available online


What: See the live version without any CGI. Winner of seven Tony Awards including Best Musical, CATS tells the story of one magical night when an extraordinary tribe of cats gathers for its annual ball to rejoice and decide which cat will be reborn.

When: On until January 5
Time: Times vary
Where: Princess of Wales Theatre — 300 King Street West
Admission: Tickets start at $39, available online

Die Hard

What: Christmas movie or not, it’s the time to watch John Mclean take Gruber out. See Bruce Willis at the peak of his powers as an 80s action star. (He even had hair.)

When: On until December 22
Time: 7:30 pm
Where: 955 Lake Shore Boulevard West
Admission: $15, available online

The Music Of “A Charlie Brown Christmas” 

What: Head to the Dakoda Tavern for an all-ages rendition of the music from A Charlie Brown Christmas. It’ll be full of good feels and great options from the kitchen.

When: Saturday, December 21
Time: 2 to 4 pm
Where: The Dakota Tavern, 249 Ossington Avenue
Admission: $10, available online

Saturday Family Clay

What: Every Saturday is a family art day at LucSculpture. Head down and learn some of the basics of sculpting figures, building hand objects, and creating with your kids. They’ll fire all the pieces after you’re done.

When: Every Saturday
Time: 1:00 to 4:30 pm
Where: LucSculpture Art School — 663 Greenwood Avenue
Admission: $15 to $35, tickets available online

stackt chalet

What: Good Kids and stackt present an Aprés-Ski day party. Wrap up the 27 day Holiday Hills festival with an 80’s video dance party with ski shots, s’mores, snow cones, a costume contest, and more.

When: Sunday, December 22
Time: 4 to 10 pm
Where: stackt Market, 28 Bathurst Street
Admission: $12.94, available online

Hedwig and the Angry Inch

What: See John Cameron Mitchell’s instant cult classic. It’s the story of Hedwig, a wo(man) scorned. After emigrating from East Berlin to America and surviving a botched operation as well as a string of scarring relationships, Hedwig, in all her Iggy Pop meets Courtney Love glam-punk glory, has finally found her voice.

When: Monday, December 23
Time: 9 pm
Where: Paradise — 1006 Bloor Street West
Admission: $14, available online

Love Shack : Yak Shaving Day!

What: Come shave the sacrificial yak, drink drinks and listen to excellent tunes. It’s time to get weird. Also, there is 100% no Christmas music allowed. DJ DangerCat will be playing all the best rock & roll, indie, surf, garage, and new wave hits all night.

When: Wednesday, December 25
Time: 9 pm
Where: Swan Dive — 1631 Dundas Street West
Admission: Free

Drakemas: Drake Holiday Dance Party

What: Don’t be upset this holiday season. Call the broskis and head out to a ridiculous event. Show your love for this great city of ours by celebrating everyone’s favourite member of the Raptors, Drake.

When: Saturday, December 28
Time: 10 pm to 2 am
Where: Sneaky Dee’s, 431 College Street West
Admission: $5, available online

What’s in the Box

What: What’s in Box Music Festival (WITB) is where the plethora of Canadian talent — from DJs, to singer-songwriters, to cultural producers – get to showcase their music, their ideas and visions. It’s five days of increadible art.

When: December 26 to 30
Time: Times vary, check online
Where: The Drake Hotel — 1150 Queen Street West
Admission: $5, available online

Light Up the Dark

What: Light Up the Dark returns for three evenings this season. Bring family and friends to watch as 3D projection mapping transforms the Museum’s façade into a series of colossal artworks. There will also be pop-up performances and the museum will be open late.

When: December 27 to 29
Time: 6 to 9 pm
Where: Aga Khan Museum — 77 Wynford Drive
Admission: Free

DisasterFEST 2019

What: It’s a six hour marathon of wild, weird, and experimental comedy. Every 10 minutes is a new show that is gets wilder than the next. Don’t bring the kids to this show. It’s a raunchy time of no holds barred comedy.

When: Friday, December 27
Time: 8 pm
Where: Bad Dog Comedy Theatre — 875 Bloor Street West
Admission: $20, available online

Ashley with a ‘Y’

What: An awe-inspiring mix of cabaret, raconteuring and quick-as-lighting musical improv, watch Ashley Botting perform most people’s worst nightmare, and ever-so glamorously. Collecting audience suggestions at the beginning of the show, Botting, with the aid of gifted pianist Scott White, tackles everything from the mundane to deep human truths, in improvised song.

When: Saturday, December 28
Time: 9 pm
Where: Paradise — 1006 Bloor Street West
Admission: $33, available online

Polar Bear Skate at The Bentway

What: Strip down to your skivvies and hit the trail. The Polar Bear Skate is free to attend — just bring your skates and you’re good to go. If you don’t have skates, there are rentals onsite.

Ready to brave the cold? All participants must sign a waiver before taking part in the Polar Bear Skate

When: Sunday, December 29
Time: 1 to 4 pm
Where: The Bentway — 250 Fort York Boulevard
Admission: Free

Canada’s Ballet Jörgen – The Nutcracker

What: Ballet Jörgen’s interpretation of Tchaikovsky’s well-loved score blends a magical classic tale with Canadian twists. Created by acclaimed choreographer and Artistic Director Bengt Jörgen, this returning festive-favourite is set against the rugged beauty of the Canadian landscape as seen through the eyes of the Group of Seven.

When: December 30 and 31
Time: Times vary
Where: Flato Markham Theatre — 171 Town Centre Boulevard
Admission: $15 to $50, available online

New Year’s Eve at the CN Tower

What: Dance the night away on the CN Tower’s glass floor as the DJ spins Top 40 hits. Tantalize your taste buds with delicious local cuisine, including roast beef tenderloin, Ontario artisanal charcuterie and cheeses, bao buns, tacos and passed hors d’oeuvres and sweets. Party favours and poutine at midnight.

When: Wednesday, December 31
Time: 9 pm
Where: CN Tower — 301 Front Street West
Admission: $200, available online

New Year’s Eve at Nathan Phillips Square

What: Toronto’s annual New Year Eve’s celebration featuring DJ skating parties, live musical performances, and spectacular fireworks. Admission is free to this all-ages, alcohol-free event.

When: Wednesday, December 31
Time: Starts 8:50 pm, fireworks at midnight
Where: Nathan Phillips Square
Admission: Free

Slut Parade: A Sex Positive Comedy Show

What: Slut Parade is a sex positive comedy show hosted by Allie Pearse and a collection of Toronto’s best standup comedians sharing their best and worst stories of the sex and dating world.

When: Thursday, January 2
Time: 8 pm
Where: Comedy Bar — 945 Bloor Street West
Admission: $20

With It 60s Soul Record Dance Party

What: It’s the perfect 60s dance event. Enjoy Mod Soul, R&B, R&R, Garage Funk, and more all from the era spun up by DJ Parka Pat from Montreal along with local man DJ Nico.

When: Saturday, January 4
Time: 10 pm
Where: The Piston — 937 Bloor Street West
Admission: $10

Toronto Maple Leafs Skate for Easter Seals Kids

What: The Toronto Maple Leafs Skate for Easter Seals Kids is a fundraising event that offers fans the opportunity to skate with Toronto Maple Leafs players and alumni in support of Ontario’s kids with physical disabilities.

When: Sunday, January 5
Time: Noon
Where: Ford Performance Centre — 400 Kipling Ave
Admission: $250 minimum fundraising, register online

Julius Caesar

What: In the most powerful state on earth, a coalition of educated elites, alarmed at their leader’s populist, authoritarian reforms, conspire to bring him down. After his assassination, a civil war erupts, as ghosts, revolutionaries, and politicians contend with what they’ve done, and what’s to come.

When: January 7 to 26
Time: Times vary
Where: Crow’s Theatre — 345 Carlaw Avenue
Admission: Tickets $30 to $55

Beer and Cheese Pairing

What: Beer and cheese, the best of pals, come together in one tasty event. Join your fellow brew lovers for a house beer and cheese pairing in partnership with The Art Of Cheese. Enjoy five different kinds of cheese paired with five 5 oz tasters of Rorschach beer.

When: Thursday, January 9
Time: 7 pm
Where: Rorschach Brewing Co. — 1001 Eastern Avenue
Admission: $20, available online

9th Annual Toronto Tango Marathon

What: Head out for an amazing weekend of Argentine Tango in Toronto, with beautiful music, a great venue, lots of dancing, and delicious refreshments. There will be DJs to keep you dancing to the wee hours. Get ready for three days and three nights of non-stop Tango.

When: January 10 to 12
Where: The Continental Dance Club — 3141 Wharton Way
Admission: Prices vary, register online

Partners in Art present Beyond the Visible: Hilma af Klint

What: Watch history get rewritten as Swedish artist Hilma af Klint finally takes her rightful place in history as a pioneer of abstract art. Over a century after her first boldly colourful painting got eclipsed by Wassily Kandinsky, she became the subject of a monumental Guggenheim exhibition, “Paintings for the Future”—at last getting the credit she deserves. This documentary explores why it took so long.

When: Sunday, January 12
Time: 6:30 pm
Where: Hot Docs Ted Rogers Cinema — 506 Bloor Street West
Admission: $11.50, available online


What: This art installation is an interactive retro-futuristic machine powered by you. Visitors can hop on two at a time into one of the six illuminated cylinders and pump a lever to activate the lights and glowing images within the loop.

When: January 15 to February 9
Where: York Street Park — York and Harbour Streets
Admission: Free

F*ckup Nights Toronto Vol XXXI

What: F*ckup Nights Toronto is part of a global speaker series where stories of failed businesses and projects are shared in 330+ cities and 86+ countries. Each speaker is given 10 minutes and is able to use 10 images. After each speaker, there’s a Q&A session, as well as time for mingling and drinks.

When: Thursday, January 16
Time: 6:30 to 9:30 pm
Where: Shopify — 620 King Street West
Admission: $20 to $25, available online

Blue Jays Winter Fest

What: Winter Fest is returning for its third straight year, featuring two days of baseball fun and winter festivities. Activities include Blue Jays current player, alumni, and rookie appearances; kids activities; live entertainment; historic memorabilia; ballpark tours; and much more. Plus, the first 12,000 fans attending Winter Fest each day will receive a Blue Jays Toque

When: January 18 and 19
Time: 10 to 5 pm
Where: Rogers Centre — 1 Blue Jays Way
Admission: $20, available online

Toronto Pug Grumble

What: Bring your pugs to the Dog Bowl in Trinity Bellwoods Park this Sunday for a Toronto Pug Grumble. Get ready for lots of snorting, rolling, and grumbling. It’s basically the cutest thing going on in the city this weekend.

When: Sunday, January 19
Time: 2 to 4 pm
Where: Dog Bowl in Trinity Bellwoods Park
Admission: Free

Toronto Night Time Record Show

What: The historic Monarch Tavern will once again play host to 10 fully stocked tables of vinyl goodness for your perusal and consumption. All styles of music will be represented, from vintage treasures to the latest wax. We’ll also be spinning the good stuff all night for you to groove to whilst digging.

When: Thursday, January 24
Time: 6 pm
Where: Monarch Tavern — 12 Clinton Street
Admission: $3

Toronto Human Rights Watch Film Festival

What: See some of the most powerful documentary films of some of the most serious issues happening in the world today. The annual Toronto Human Rights Watch Film Festival brings human stories to life in a manner that empowers the audience to demand justice for all.

When: January 30 to February 4
Time: Times vary
Where: Hot Docs Ted Rogers Cinema — 506 Bloor Street West
Admission: Free


What: It’s a celebration of food in the heart of winter. There will also be more than 200 restaurants offering prix-fixe lunch and dinner menus for the duration of the event, including Bar Buca, East Thirty-Six, Pukka, and Wish. Lunch menus will be priced at $23, $28, and $33 and dinner menus at $33, $43, and $53.

When: January 31 to February 13
Where: Across Toronto
Admission: Prix-fixe menus

Secret Life of a Mother

What: A playwright writes her exposé of modern motherhood in a confessional piece about her own darkly funny and taboo-breaking truths. These mothers are not the butts of jokes, or the villains, or the perfect angels of the house.

When: February 5 to 23
Time: Times vary
Where: Crow’s Theatre — 345 Carlaw Avenue
Admission: $39.55, available online

Women In Horror Month- Short Film Showcase 2020

What: It’s a showcase of some of the best female-driven horror and genre movies in the space right now. This showcase will feature films from across the world, including one from right here in Canada.

When: Thursday, February 6
Time: 8 pm
Where: Eyesore Cinema — 1176 Bloor Street West
Admission: $8, available online

Post Malone – Runaway Tour

What: Congratulations, Toronto, Posty is back in the city. See the combination singer and rapper in all his face tattooed glory.

When: Friday, February 14
Time: 8 pm
Where: Scotiabank Arena — 40 Bay Street
Admission: Tickets currently start at $75, available online


What: There is no lack of increadible music this season. TIESTO, once voted the best DJ in the world, is spinning in Toronto this winter. See the living legend himself live at Rebel.

When: Saturday, February 15
Time: 10 pm
Where: Rebel — 11 Polson Street
Admission: Tickets currently start at $108, available online

Winter Stations 2020

What: The winners have yet to be announced, but the city has taken in 250 submissions to the annual art competition. The artists selected will have their work displayed publically for all to see. This year’s theme is the five senses.

When: February 17 to March 30
Where: Woodbine Beach — 1675 Lake Shore Blvd East
Admission: Free

Trixie Mattel: Grown Up

What: Trixie Mattel is all grown up. Join the glamorous woman for an evening packed with music, comedy and unnecessary costume changes. Backed by a live band for the first time, this show will leave you jamming with flower power and wondering how the skinniest legend grew into the world’s funniest comedienne.

When: Saturday, February 22
Time: 7 pm
Where: The Danforth Music Hall — 147 Danforth Avenue
Admission: Tickets start at $55, available online

Cult Of Luna

What: The Swedes are coming. And with them comes a unique blend of heavy metal and soulful sounds. Cult of Luna is descending upon the city, and if you’re a new fan or an old one, it’s time to have some fun.

When: Tuesday, March 3
Time: 7 pm
Where: The Opera House — 735 Queen Street East
Admission: $37.50, available online

The Lumineers – III: The World Tour

What: See The Lumineers as they tour to promote their new album, III. Each purchase of a ticket comes with a free digital copy of the album. Also appearing will be Mt. Joy and J.S. Ondara.

When: Wednesday, March 4
Time: 7 pm
Where: Scotiabank Arena
Admission: $71, available online

Laugh Sabbath

What: A comedic force in this city, Laugh Sabbath has been showcasing some of the best comedic minds in North America for years. Many alum have gone onto big roles on TV and movies. See the next Canadian comedic superstar here.

When: Thursday, February 27
Time: 9:30 pm
Where: 945 Bloor Street West
Admission: $5

The Wizard Beer Festival

What: It’s another non-brand specific wizard themed brew event. This one comes including local DJs, tarot card readers, wand and potion making classes, and dry ice to set the mood — always need dry ice. Included in your ticket, will be a 12oz welcome beer and five tokens that will give you access to various beer and activity stations.

When: Sunday, March 1
Time: 7 pm
Where: CRAFT Beer Market — 1 Adelaide Street East
Admission: $45, available online

Destroyer at the Opera House

What: Destroyer is a Canadian rock band from Vancouver, British Columbia fronted by singer-songwriter Dan Bejar. Destroyer songs are characterized by abstract, poetic lyrics and idiosyncratic vocals.

When: Wednesday, March 4
Time: 8 pm
Where: The Opera House — 735 Queen Street East
Admission: $25, available online


What: Launched seven years ago Mindfest began as a unique initiative to promote awareness, dialogue, and understanding about mental health and mental illness. Come see the latest advances in the field and network with people and resources available in Toronto.

When: Wednesday, March 11
Time: 9:30 am to 4:30 pm
Where: Hart House, 7 Hart House Circle
Admission: Free

MILF Life Crisis

What: It’s a heartfelt and hilarious comedy, MILF Life Crisis. Anne Marie Scheffler discovers an amazing life after divorce and that the best is yet to come in this one-woman show.

When: Friday, March 13
Time: 8 pm
Where: Flato Markham Theatre — 171 Town Centre Boulevard
Admission: $15 to $40, available online

Toronto Motorama Show

What: The sixth annual Motorama Custom Car & Motorsports Expo will feature a two-day appearance by Chip Foose, the pre-eminent star in the automotive design and fabrication industry as well as some of the best vendors and names working in the field right now.

When: March 13 to 15
Where: The International Centre — 6900 Airport Road

Assassin’s Creed Symphony

What: Assassin’s Creed Symphony is a multimedia symphonic project that delivers an innovative and immersive new take on the music of the Assassin’s Creed franchise. For the very first time, both seasoned fans and symphony-goers can experience the rich musical history of the popular saga in a live music setting with new takes on the best tracks from the franchise.

When: Saturday, March 14
Time: 7 pm
Where: Meridian Hall — 1 Front Street East
Admission: Tickets start at $66, available online

Taste of Little Tokyo with @EatingThroughTO

What: Toronto Common and Eating Through TO wis bringing back their popular Taste of Little Toyko Tour. Toronto’s newest cultural pocket has attracted famous food and fashion brands such as Muji, Pablo Cheesecake, and Uncle Tetsu’s. Not to mention the locally owned and time-tested Izakayas and sushi restaurants on the strip.

When: Sunday, March 15
Time: 1 pm
Where: Rolltation — 207 Dundas Street West
Admission: $60, available online

Peter SmithPeter Smith

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