51 winter events to check out in Toronto

Dec 5 2016, 2:01 am

It looks like we’re going to be ending 2016 and starting 2017 on a high note, as our winter calendar is already bursting with events and attractions.

From taking a chilly plunge in the Lake Ontario on New Year’s Day Swim to laughing your socks off at one of the many upcoming stand-up comedy shows, there are so many wonderful things to do in the winter in Toronto.

Here are 51 reasons you’re not allowed to be a shut in this winter in Toronto.


Toronto Christmas Market

What: Toronto’s Christmas Market brings the spirit of the season to life. One of Toronto’s favourite holiday events, guests are invited to rediscover the magic and romance of Christmas by taking in stunning light canopies, enjoying unique shopping experiences, traditional music and dance performances, and activities for the whole family to enjoy. Admission is free Tuesday to Friday.

When: Now until December 22
Where: Distillery Historic District, 55 Mill Street

Union Station Holiday Market

What: Head down to Toronto’s busiest transit hub this December to visit the Union Station Holiday Market. This holiday market features a curated mix of approximately 20 local businesses, designers, artisans and gourmet food vendors offering a selection of the city’s best gifts.

When: Now until December 16
Where: Union Station, 65 Front Street West

Sister Act The Musical

What: Based on the hit film, Sister Act tells the hilarious story of Deloris Van Cartier, a wannabe diva whose life takes a surprising turn when she witnesses a crime and the cops make her go into hiding at a convent.

When: Now until January 29 (every Thursday), 7:30 to 9:30 pm
Where: Lower Ossington Theatre, 100A Ossington Avenue

Holiday Fair in Nathan Phillips Square

What: Santa will be setting up his workshop in the heart of downtown Toronto at the Nathan Phillips Square Holiday Fair. Guests are welcomed into the warmth of Santa’s home for a meet-and-greet and holiday photos, plus kids can write letters to Santa, meet an elf or two and build a stuffed toy.

When: Now until December 23
Where: Nathan Phillips Square, 100 Queen St West

Holiday Market

What: This outdoor market will feature a collection of seasonal and artisan vendors, live music, food and drink, a warm-up lounge hosted by Jack Astor’s and a strolling Santa.

When: December 9 to 11, and 16 to 18, Fridays from 3 to 9 pm, Saturdays & Sundays from 12 to 6 pm
Where: Shops at Don Mills, 1090 Don Mills Road

The Nutcracker

What: Ever since its premiere in St. Petersburg in 1892, The Nutcracker has been an integral and irreplaceable part of Christmas celebrations worldwide and a work of theatrical exuberance synonymous with the unfettered joys of childhood wonderment. The National Ballet of Canada’s touching and multilayered version of the famous ballet, choreographed by James Kudelka, is a spectacular re-imagining that has been greeted with rapturous acclaim by audiences whenever it is performed.

When: December 10 to 31
Where: Four Seasons Centre for the Performing Arts, 145 Queen Street West

Gladstone Flea: Holiday Market

What: The Gladstone Hotel teams up with notable fashion and lifestyle aficionados to jury an organized, handpicked, marketplace. Packed with artist goods, reclaimed vintage, craft, design, jewelry, clothing, and more. It’s a perfect local spot to cross names off that list, and find yourself a gem or two.

Where: The Gladstone Hotel, 1214 Queen Street West
When: December 11 from 10 am to 4 pm

A Jann Arden Christmas

What: Jann Arden & the Toronto Symphony Orchestra will be uniting forces this holiday season. Jann Arden will be performing a memorable assortment of timeless numbers and audience favourites. The TSO is joined by the Etobicoke School of the Arts Chorus, under the baton of TSO Principal Pops Conductor Steven Reineke.

When: December 13 at 8 pm
Where: Roy Thomson Hall, 60 Simcoe Street

Ugly Christmas Sweater Cocktail Cruise

What: This 2-hour holiday cruise through the Toronto Harbour will include food stations, a costume contest (ugliest outfit wins, and a complimentary Bad Santa photo booth.

When: December 16 at 9 pm
Where: Mariposa Cruises – Pier 6, 207 Queens Quay West

Home Alone Quote-Along

What: Because what is the holiday season without a little Kevin McAllister? Clearly a fan fave, this is the third annual Hot Docs Home Alone Quote-Along. Get ready to get rowdy!

When: December 16 at 9:30 pm
Where: Hot Docs Ted Rogers Cinema, 506 Bloor Street West

Let it Snow: Craft Fair

What: The 2nd Annual Let it Snow Craft Fair returns, bringing together talented local artisans from across Toronto.

When: December 16 to 18
Where: Artscape Youngplace, 180 Shaw Street

Christmas Marketplace

What: Presented by the Toronto Etsy Street Team, Christmas time is prime time for craft shows and this is one cozy, intimate handmade show, on the LAST shopping weekend before Christmas. There will be festive music, handmade goods and plenty of vintage sellers, and yummy snacks.

When: December 17 from 11 am to 5 pm
Where: Church of Saint Stephen-in-the-Fields, 103 Bellevue Ave at College Street


What: Hallelujah! Experience Handel’s Messiah, Toronto’s must-see holiday classic, performed with matchless spirit by the Toronto Symphony Orchestra. Acclaimed Baroque-music specialist Nicholas McGegan conducts the Orchestra and a stellar lineup of vocalists and chorus, in five tremendous performances of the immortal oratorio.

When: December 18 at 3 pm
Where: Roy Thomson Hall, 60 Simcoe Street

City of Toronto Christmas Concert

What: Celebrate the holiday season at the City of Toronto’s annual Christmas Concert. Beginning at 11:30 am in the Rotunda of City Hall, the concert will feature local choirs: All the King’s Voices, Toronto Beaches Children’s Chorus and Toronto Mass Choir. They will be joined by the Tower Brass and organist James Bourne, while popular Toronto media personality Adam Wylde will once again emcee. As always, Santa Claus will make a special guest appearance.

When: December 23, 11:30 am
Where: City Hall, 100 Queen Street West

Christmas Dinner at One King West

What: Don’t feel like cooking a turkey dinner this year? Come to One King West for a delicious Christmas dinner and spend time with your loved ones while you relax and enjoy each other’s company.

When: December 24 & 25, 5:30 pm to 11 pm
Where: One King West, 1 King Street

2017 IIHF World Junior Championship

What: Toronto plays host to the preliminary round for the Canadian team at the 41st World Junior Hockey Championships.

When: December 26 to January 2
Where: Air Canada Centre, 50 Bay Street

ROM New Year’s Eve

What: Get dressed to the nines and celebrate the new year in style at #ROMNYE. Here you can dance the night away while enjoying delectable bites and drinks, check out the exhibition CHIHULY, live bands, DJs, and, of course, enjoy a sparkling toast at midnight.

When: December 31 at 9 pm
Where: Royal Ontario Museum, 100 Queens Park

Back in the Day NYE

What: 90s lovers rejoice: It’s time to take a walk down memory lane and get nostalgic as Back In The Day NYE will be tributing Old School Hip Hop, R&B, Dance, House, Reggae, & Pop from the 90s.

When: December 31 to January 1, 10 pm to 4 am
Where: 99 Sudbury, 88 Sudbury Street

 A Very Bowie New Years Eve

What: Ring in the New Year as you pay tribute to the one and only Bowie. There will be plenty of party favours and bubbly at midnight and the best part? No cover.

When: December 31 to January 1, 9 pm to 1 am
Where: Old Nick, 123 Danforth Avenue

DJ Skate Nights: A NYE Ice Skating Jam

What: Count down to the New Year with the whole family at DJ Skate Nights: A NYE Ice Skating Jam Named Saturdays, as DJ P-Plus serves up the hottest hits.

When: December 31, 8 pm to 1 am
Where: Natrel Rink, 235 Queens Quay West


The Courage Polar Bear Dip

What: Join hundreds of dippers at Coronation Park in Oakville as they take the plunge into the icy cold waters of Lake Ontario to help provide clean water in developing countries.

When: January 1, 12:30 pm
Where: Coronation Park, Oakville

2017 Centennial Classic : Toronto vs Detroit

What: Cheer on your boys in blue as they take on the Detroit Red Wings and celebrate 100 years of Maple Leaf hockey.

When: January 1, 12 pm
Where: BMO Field, 170 Princes’ Boulevard

Toronto Polar Bear Dip

What: Come and ring in the new year with a daring plunge into the icy waters of Lake Ontario in support of affordable housing in the GTA.

When: January 1, registration opens at 10:30 am, dip at 12:00 pm sharp
Where: Sunnyside Park, 1755 Lake Shore Blvd West

Next Stage Theatre Festival

What: The NSTF will be celebrating its 10th birthday this season and since launching in 2008, the festival has grown into the premier showcase of Fringe talent in Canada. There will also be a heated Steam Whistle Tent, so attendees can grab a drink and meet friends before or after their show.

When: January 4 to 15
Where: Factory Theatre, 125 Bathurst Street

Kensington Market Food Crawl

What: Taste your way through Toronto’s most unique and eclectic neighbourhood on a culinary excursion through Kensington Market. As you explore the market, you will learn about its history and heritage, meet local shopkeepers and chefs, and indulge in a variety of delicious foods and drinks.

When: January 6, 7 and 8, 11:30 am to 3 pm
Where: Kensington Market, 191 Baldwin Street

Art, Vibes, Fashion

What: This event will consist of a series of  visual artist (painters), fashion designers, boutique owners, singers, comedians displaying their talents in a showcase like setting.

When: January 13, 2 pm to 5 pm
Where: 360 Geary Avenue

Kings of Leon

What: Put on your dancing shoes, because Kings of Leon return to Toronto for their Walls tour to promote their highly anticipated seventh album.

When: January 16, 7:30 pm
Where: Air Canada Centre

Canada Job Expo

What: Whether you are a graduate, unemployed, new to Canada, a seasoned veteran looking to change careers, or a student new to the workforce, the Canada Job Expo is perfect place to launch your career. Here you’ll find plenty of information, job resources and discussions and opportunities for employment.

When: January 19, 10 am to 3 pm
Where: North York Memorial Hall, 5110 Yonge Street

Sam Roberts Band

What: The Sam Roberts Band will be hitting the stage in Toronto with special guests Hollerado to perform their sixth full-length album, TerraForm.

When: January 20, 9 pm
Where: Rebel, 11 Polson Street

Carrie the Musical

What: Carrie is constantly tormented at school by the ‘cool’ kids and smothered at home by her religious mother. She’s had enough and now she has her own unique way of getting back at them. Carrie the Musical shows us just what happens when bullies push too far.

When: January 20 to February 4, 8 pm
Where: Hart House Theatre, 7 Hart House Circle

Toronto Boat Show

What: The Toronto International Boat Show is the largest one-stop destination in Canada to comparison shop and find the newest and most innovative boats, fishing and outdoor products, water toys, services, and marine accessories from over 550 exhibitors offering the best deals of the year.

When: January 21, 10 am to 7 pm
Where: Enercare Centre, 100 Princes’ Boulevard

Ice Breakers

What: Along Toronto’s waterfront there will be a series of wintertime art installations at public locations along Queens Quay West. At Harbourfront Centre, HTO Park, Rees Street Parkette, Peter Street Basin & the Music Garden.

When:  to

3rd Annual Vintage Prom

What: Toronto’s biggest Vintage Dance Party is back for the 3rd Annual Vintage Prom. This year’s theme: “Socs VS Greasers”.

When: January 21, 8:30 pm to 2 am
Where: The Great Hall, 1087 Queen St West

Brett Kissel – Ice, Snow & 30 Below Tour

What: Calling all country music fans: 2016 CCMA Male Artist of the Year and Fans’ Choice Award Winner Brett Kissel will be hitting the stage at the Danforth Music Hall.

When: January 22, 6:30 pm to 11 pm
Where: The Danforth Music Hall, 147 Danforth Avenue

Cross Stitching With Caitlin

What: Cross Stitching with Caitlin is a two-hour workshop that is being held at the Left Field Brewery. Beer and cross stitching, what’s better than that?

When: January 25, 6:30 pm to 8:30 pm
Left Field Brewery, 36 Wagstaff Drive


What: Come and experience mouthwatering cuisine from around the world at great prix fixe value at some of the city’s top restaurants. There’s a cuisine for everyone as there’s a wide variety of restaurants and types of cuisine to choose from.

When: January 27 to February 9
Where: Restaurants throughout the city


Motion Ball

What: An unparalleled evening filled with entertainment, networking and socializing with proceeds going to support the Special Olympics Canada Foundation, Motion Ball is the must-attend event for young professionals this winter.

When: February 3
 Liberty Grand, Exhibition Place

Blue Rodeo

What: Canada’s premier rock band Blue Rodeo will be hitting the stage of Massey Hall with special guests Ron Hawkins and The Do Good Assassins.

When: February 3, 7 pm to 10 pm
Where: Massey Hall, 178 Victoria Street

Red Hot Chilli Peppers

What: The Red Hot Chilli peppers are heading out for a huge world tour, making this their first road trip since 2014. This tour will be supporting their latest album “The Getaway” and it’s a show you won’t want to miss.

When: February 4, 8 pm
Where: Air Canada Centre

Switchfoot and Relient K

What: Switchfoot will be performing their new album “Where The Light Shines Through” alongside Relient K at The Phoenix Concert Theatre.

When: February 8, 630 pm to 930 pm
The Phoenix Concert Theatre, 410 Sherbourne Street

Abba Mania

What: Alright you dancing queens, Abba Mania will be hitting up the Danforth Music Hall for a night you surely won’t forget. The concert is a Canadian produced rock musical which takes you back to the disco era of one of the best pop bands in history, ABBA.

When: February 2, 7 pm
Where: The Danforth Music Hall, 147 Danforth Avenue

The National Symphony Orchestra of Ukraine

What: This distinguished ensemble displays its brilliance, warmth, and expressive versatility in splendid works by Tchaikovsky and Stankovych — with the excellent Ukrainian violinist Dima Tkachenko as soloist.

When: February 10, 7:30 pm to 9:30 pm
Roy Thomson Hall, 60 Simcoe Street

Canada All Star Ballet Gala

What: The most prestigious ballet gala in the world, this performance is the first of its kind and a celebration of Classical Ballet Masterpieces. It will be performed by the world’s most accomplished artists from Paris Opera Ballet, Royal Ballet of London, The Bolshoi of Russia, The National Ballet of Canada, Rome Opera Ballet, American Ballet Theater, Royal Danish Ballet and San Francisco Ballet.

When: February 11, 7:30 pm to 10:15 pm
Where: Sony Centre for the Performing Arts, 1 Front Street East

Amy Schumer

What: This is the Trainwreck star’s postponed standup show, after canceling her Canadian tour stops this November. Make sure to grab your tickets fast, as this event is expected to sell out.

When: February 16, 8 pm
Where: Air Canada Centre

Community Quilt Group Get-Together

What: Relax and meet new friends while you improve your sewing skills as you explore both historic and contemporary quilting techniques in a comfortable, social setting.

When: February 16, 6 pm to 8 pm
Where: Gibson House Museum, 5172 Yonge Street

Jerry Seinfeld

What: America’s premier comedian Jerry Seinfeld will return to Toronto to perform his signature stand-up routine live at the Sony Centre for the Performing Arts. Don’t miss your chance to see this comedy legend perform.

When: February 17 and 18 at 7 pm and 9:30 pm
Where: Sony Centre for the Performing Arts

Canadian International Autoshow

What: The Canadian International Autoshow will feature over 600,000 square feet of dazzling displays, exotic cars, big prize giveaways and plenty of engaging exhibits.

When: February 17 to 26
Where: Metro Toronto Convention Centre

Toronto Symphony Orchestra, Disney-Pixar “Ratatouille” In Concert

What: Calling all Disney fans, Pixar’s most enchanting animated film ‘Ratatouille’ will be coming to Toronto as the TSO will be playing the score from the film.

When: February 18, 4:30 pm to 6:30 pm
Where: Roy Thomson Hall, 60 Simcoe Street

Wedding Open House

What: For those tying the knot this year, The Old Mill will be opening its doors as part of its annual open house to show off the grounds and its preferred wedding vendors.

When: February 22, 430 pm to 8 pm
Where: Old Mill Toronto, 21 Old Mill Road

The Best of The Second City

What: The Best of The Second City features an ever-changing selection of the best and funniest sketches from the past fifty years, as well as the improvisation for which Second City is famous.

When: February 24, 10 pm
Where: The Second City, 51 Mercer Street

The Wedding Co. Market

What: The Wedding Co. Market is a cozy winter marketplace for Toronto couples seeking to be inspired by local wedding industry members who are passionate about their craft and who take pride in offering exceptional service.

When: February 26
Where: Artscape Wychwood Barns, 601 Christie Street

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