The Christmas lights are up, jingle bells are ringing, and the holiday festivities have officially commenced in Toronto. From winter villages to seasonal pop-up bars, there’s something for everyone to celebrate the jolly season. With ice skating rinks opening in several city corners and live events featuring holiday music, there’s lots to see and do.
To narrow down your festive season itinerary, SheDoesTheCity lists more than 18 merry attractions to choose from, including improvised holiday musicals, Christmas markets, and immersive performances that’ll keep you in high spirits.
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The Second City Holiday Shows
Holiday hilarity awaits at Second City’s holiday shows, featuring three new productions that are stuffed with songs, sketches, and improv. Rizz the Season delivers on unhinged comedy chaos and boasts an all-star cast of Canadian performers. Let It Snow blends classic sketches from Second City’s archives and new material that’ll add laughter and joy to the audience’s holiday season. Rudolph Runs Wild promises to entertain the entire family with a one-of-a-kind interactive theatrical experience that includes plenty of improv hijinks. More info.
When: December 3-January 4
Where: The Second City
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Toronto Symphony Orchestra Holiday Shows
The TSO will ring in the end-of-year festivities with music performances that’ll instantly put you in a jolly spirit. This week, listen to the orchestra play John Williams’ delightful score live during a screening of Home Alone. Up next are the TSO Holiday Pops, where audiences will get to enjoy festive tunes led by guest conductor Sarah Hicks, with soaring vocals from Mikaela Bennett. Later in the month, delight in a magnificent showcase of Handel’s Messiah, featuring the heavenly voices of the Toronto Mendelssohn Choir. More info.
When: December 4-21
Where: Roy Thomson Hall
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The Nutcracker
The Nutcracker has become a Toronto holiday tradition for the past 30 years, and The National Ballet of Canada is thrilled to celebrate this milestone. With choreography by James Kudelka, brace yourselves for the return of a ballet classic, with dancers taking the stage and performing to Tchaikovsky’s memorable compositions. Embark on an adventurous journey with Marie and Misha, as the two siblings encounter magical creatures and the glittering land of the Sugar Plum Fairy. More info.
When: December 5-31
Where: Four Seasons Centre for the Performing Arts
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Christmas at the Castle and Holiday Lights
There is nothing more enchanting than visiting a castle that’s been adorned with holiday decorations. Every year, Casa Loma invites guests to spend Christmas at the Castle, participating in interactive activities, watching thrilling performances by aerialists, mascots, and magicians, as well as delight in holiday music sung by Sara Papini. After hours, guests can also wander through the castle grounds with Holiday Lights, a wintry experience marked by light installations. Some of them are even located inside Casa Loma’s famous underground tunnels. More info.
When: December 5-January 3
Where: Casa Loma
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Festive Nights
Step into a world of wonder as the Village at Black Creek glows with traditional lights. Wander inside lantern-lit buildings, indulge in delicious holiday treats (anything from gingerbread cookies to roasted chestnuts), and catch some music and storytelling performances. Santa’s Cottage will also be open, with Kris Kringle ready to hear your holiday wishes, whether you’ve been naughty or nice. More info.
When: December 6, 13, and 20
Where: Village at Black Creek
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Holiday! An Improvised Musical
You are in for a treat with Holiday! An Improvised Musical. After all, no performance is the same as the previous one, since the audience is directly responsible for shaping the show they want to see. Inspired by Stephen Sondheim’s Company, this musical is improvised on the spot, as a wildly talented cast takes suggestions from the crowd before coming up with their next bit. Despite not knowing what you are in for, audiences can expect a performance that captures the true meaning of the holiday season by exploring themes like love and family. More info.
When: December 10-20
Where: Factory Theatre
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Winter Glow
Sankofa Square will look extra festive with the return of Winter Glow. Downtown Toronto will transform into a vibrant holiday destination filled with lights, music, and festive flavours that’ll keep you in high spirits. The celebration kicks off on December 11 with a special performance by My Pop Choir and the opening of the first Ferris wheel and carousel rides of the season. There’ll also be seasonal drinks at the Polar Point Bar, photo ops with Santa Claus, and a holiday market presented by Epilepsy Toronto. More info.
When: December 11-21
Where: Sankofa Square
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A Burlesque-Mas Carol
Bah-hum-BABE! Dickens gets a queer makeover in this sassy burlesque showcase, with striptease and jaw-dropping drag being an essential part of the mix. Watch as three gorgeous ghosts of burlesque — Past, Present, and Future — shimmy, strip, and seduce Scrooge back to life. With dazzling performances, a heartwarming story of chosen family, genre-bending music, and a full bar at your service, join in on the fun and connect with audience members in this joyous celebration. More info.
When: December 12-13
Where: The Painted Lady
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Hangar Skate
The YZD Plaza will turn into an enchanted winter forest of light, music, and motion. Gather, play, and connect this holiday season at Hangar Skate, a free outdoor skating rink that has the coziest winter vibe. On December 19, you can join in on a themed skate, as the plaza glows with festive lights and cheerful music. You can also celebrate Christmas Eve at the plaza’s Winter’s Tale, filled with wintery characters and seasonal surprises. More info.
When: December 19-January 4
Where: YZD Plaza
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Winter BLOOMS: Circus at the Garden
This intimate and immersive performance features circus, nature, and a touch of seasonal magic! Rosie Petals and her playful companion Dustee the Dust Bunny invite you into a world where stories of nature and winter come alive through breathtaking circus arts. Watch aerialists, acrobats, jugglers, and clowns weave humour and wonder through this one-of-a-kind experience. Audience members are also welcome to meet the cast after the show. More info.
When: December 19-21
Where: Toronto Botanical Garden
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Winter at The Bentway
The Bentway is another ice skating location to enjoy during the holidays. Lace up and glide through the snow trail with family and friends starting December 20. During opening weekend, you can skate under the city lights, sip hot drinks, delight in maple taffy, and participate in photo moments. For those who are brave enough to ring in the new year with a bit of chill, The Bentway’s boldest winter ritual returns on December 28. At the Polar Bear Skate, Torontonians are invited to strip down to their skivvies and take a fearless lap around the trail to bid farewell to 2025. More info.
When: December 20-February 16
Where: The Bentway
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Miracle Holiday Events
Visit this Christmas-themed pop bar for tasty cocktails and warm vibes. Miracle has two locations, one on Bloor and the other at Harbourfront, both filled with kitschy decor and serving seasonal alcoholic beverages. Throughout the month of December, you can indulge in festive mornings through Breakfast with Santa and late-night glam parties presented by Vision Drag. More info.
When: On until December 21
Where: Miracle (Bloor and Harbourfront Locations)
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Holiday Hills
Rediscover the holiday magic at Holiday Hills, STACKT Market’s annual winter wonderland. From bold installations to nostalgic experiences, this is a go-to city spot to explore. Stroll through immersive displays, eat some comfort food, shop creative gifts, and enjoy weekly entertainment. Holiday Hills also features themed cocktail bars, giant holiday inflatables, and a Santa Letter Station where you can write down your wishes for the coming year. More info.
When: On until December 28
Where: STACKT Market
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Holiday at The Well
Enjoy a Nordic-inspired winter celebration at The Well, featuring seasonal activities and tasty holiday drinks. Explore the Vendor Village to shop for gifts made by local businesses, sip delicious cocktails from NORDIC by BarChef, visit the Holiday Lounge for a cozy retreat, and listen to holiday music with Silent Symphony. The Well is also hosting family movie nights every Saturday, playing holiday classics like Home Alone 2 and Jack Frost. More info.
When: On until December 28
Where: The Well
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Winterfest
The Harbourfront Centre has transformed into a Winterfest, offering festive bites at Winter Feast Lane, train rides on the Harbourfront Express, and a dose of adventure at Winter Maze. In addition, there are several seasonal activities to engage in, including the Holiday Hop dance lessons, Christmas carol performances from Amanda Martinez and The Arsenals, Winter Solstice storytelling, and a saucy-but-festive cabaret presented by Hollywood Jade. More info.
When: On until December 31
Where: Harbourfront Centre
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Distillery Winter Village
Toronto’s original and world-famous Christmas market is back, with pop-up shops, photo ops, and a dazzling tree that’ll make you even more excited about the holiday season. Different from previous years, the Distillery Winter Village is offering further opportunities to savour brand-new tastes while strolling through the historic cobblestone path. From Santa Spuds to Dubai Chocolates, there’s lots to try, plus the chance to engage in an elevated holiday dining experience at Chef’s Lane. Although not seasonal related, there is a Stranger Things pop-up at the Distillery where you can snap a picture before Season 5’s final episodes come out. More info.
When: On until January 4
Where: Distillery District
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Holiday Afternoon Tea
Drink hot tea and savour tasty seasonal delights at the AGO’s Holiday Afternoon Tea. From Uncle Ted’s Turkey Dinner to an array of bakery goods, you’ll be well-served and ready to soak in the gallery’s inspiring surroundings. The perfect activity to bring people together, this event will give you the chance to share a meal and make new memories. More info.
When: On until January 4
Where: Art Gallery of Ontario
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Cavalcade of Lights
This free, wintry celebration is taking over City Hall and its surroundings. Watch the downtown core get a winter wonderland treatment, with the glow of thousands of energy-efficient bulbs. At Cavalcade of Lights, you’ll spot a glittering tree, a public skating rink, and gorgeous light installations to ring in the jolly season. You are welcome to bring your own skates or rent them on site. More info.
When: On until January 7
Where: Nathan Phillips Square
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Union Winter
Let the good times roll by roller skating at Union Station’s indoor rink. With free rentals and skating lessons for those just starting out, this is the ideal winter activity for friends and family. To secure your time slot on the rink, you can pre-register on the site and arrive 15 minutes prior. TD credit card holders can skip the entrance line through the priority entrance on a first-come, first-serve basis. More info.
When: On until January 18
Where: Union Station
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Window Wonderland 2025
Toronto’s staple winter art exhibit will take over the Junction for the sixth year in a row with Window Wonderland. Featuring 20 artist-designed storefront windows,11 vibrant murals, and several installations brought to life with augmented reality, this open-air gallery is a go-to spot during the holidays. Window Wonderland has collaborated with the Artivive app to transform static artwork into an immersive digital experience. In addition to the artwork on display, on December 20 you can catch a one-day-only holiday performance by The Alpine Merry Sheep Choir. More info.
When: On until February 1
Where: The Junction BIA
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