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Make the most of winter at these festive holiday celebrations in Toronto 

Winter events
To make your winter plans easier, we’ve rounded up some of Toronto's best events and activities taking place in the lead-up to the holidays! (Courtesy: thebentway/ Instagram, stacktmarket/ Instagram)

Winter has arrived in Toronto and with it a slew of exhilarating events and activities! Holiday markets are popping up in every corner of the city as glistening ice rinks bustling with skaters breathe life into the downtown core.  

Whether you live in Toronto or are looking to make a trip to the city, there’s a variety of winter and festive events happening everyone can enjoy. From a new roller skating experience at Union Station to a Nordic-inspired yurt where you can sip on Scandinavian-inspired cocktails, there’s plenty to check out this season.

To make your plans easier, we’ve rounded up some of the best events and activities taking place in the lead up to the holidays!

Christmas at the Castle

(Courtesy: Casa Loma)

Embrace the festive cheer at Toronto’s iconic Casa Loma. The spectacular castle is hosting a wide range of Christmas themed activities and family-friendly events over the holiday season. 

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Admire its 40-ft. tall tree in the Great Hall and eight other signature trees decorated by talented Canadian designers, visit Santa in his grotto workshop and try your hand at arts and crafts. 

Embark on an enchanted visit with wintery holiday mascots, listen to Christmas carolers, and admire the artistry of live fire dancers and magicians scattered throughout the extravagant grounds.

Admission costs $45 per person, children under three can attend for free.

Christmas at the Castle runs from Dec. 1 to Jan. 6. To purchase tickets, click here.

Roller Express

(Courtesy: torontounion.ca)

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Roller Express, a two-month long, free roller skating experience has opened in Union Station’s newly renovated west carriageway.

The brand-new roller rink provides the perfect alternative to an icy outdoor skating session. Make the most of free skate rentals and a separate rink for first-timers to find their feet. A delectable selection of fare from Amano, Union Chicken and WVRST will also be available for purchase at this 5,500 sq. ft. roller rink that needs to be on your to-do list over the holidays.

Candles & Comedy 

(Courtesy: eventbrite)

Join North America’s best Jewish comics for a night of laughs, Channukah candles, and latkes in aid of Magen David Adom.

Chuckle at jokes and admire the quick wit of a talented lineup of Jewish comedians highlighted by the illuminating warmth of the Chanukiah. 

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Candles & Comedy promises an enjoyable night of laughs in aid of a worthy cause.

This is a one-night only event, happening on Tuesday, Dec. 12, from 7:00 p.m. -10:00 p.m. at 608 College Street.

This is an 18 + event, Tickets start at $54.

The Well’s Nordic-inspired holiday experience

(courtesy: nordictoronto)

The Well is Toronto’s most recently renovated enclave, and is fast becoming a popular playground, offering countless year-round lifestyle-focused amenities including restaurants, shops, bars and accommodations; as well as one-of-a-kind holiday activations such as the Aurora Borealis Light Display, the Veuve Clicquot Champagne Lounge, NORDIC by BarChef, musical performances, ice skating, an immersive stardust bridge, and more!

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The Well is open Monday to Sunday 11:00 a.m. to 7:00 p.m. Thursdays: 4:00 p.m. to 11:00p.m, Fridays: 4:00 p.m to 11:00p.m, Saturdays: 2:00p.m to 11:00 p.m, Sundays: 2:00 p.m to 11:00 p.m

Book your spot at Nordic by BarChef here.

The Bentway – Winter Skating

(courtesy: The Bentway)

A unique opportunity to ice skate under one of Toronto’s busiest highways, the Gardiner Expressway, is back thanks to The Bentway.

Locals and visitors are invited to navigate its 220m figure-eight ice rink, and indulge in festive favourites, including free hot chocolate, on Mondays starting on Jan. 8 between 5:00 p.m and 9:00 p.m. The Bentway also offers skating lessons and its iconic polar bear Skate. 

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It’s free to skate, and equipment rentals are available onsite, starting at $12, sizes range from youth 6 to adult 12.

Black Creek Pioneer Village

(Courtesy: Black Creek Pioneer Village) 

Santa at the Village

Become one of Santa’s helpers and try your hand at old-fashioned toy-making with Father Christmas himself. 

Give his mystical helpers a run for their money with your seasonal magic tricks at the School of Elves, craft holiday decorations, dig into Christmas cookies, indulge in a cup of hot cocoa, hand write Christmas cards for your nearest and dearest and get lost in the magic of storytelling at a classic puppet show.

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Santa at the Village takes place on December 2, 3, 9, 10, 16, 17, and 23, from 12:00 p.m. to 4:00 p.m.

Adult tickets cost $22.00 + HST, Senior/ Student: $20 + HST, Child (3 to 14): $18.00 + HST, and members have free admission. 

To book tickets, click here.

Festive Nights

Basque in the joy of the festive season with a moonlit experience at the village. Sip on a cup of peppermint hot chocolate and enjoy an evening of nostalgic seasonal pastimes, including a puppet show, old-timey parlour games, and classic holiday crafts.

Enjoy live entertainment and sample traditional holiday treats, from roasted chestnuts to gingerbread cookies. Get lost in a winter’s tale told by a professional storyteller, and take part in playful country dancing. Before you go be sure to stop by Santa’s cottage and say hello to Kris Kringle himself.

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Festive Nights will take place on Saturday, December 2, 9, and 16, from 6:00 p.m. to 9:00 p.m.

Adult (15+) non-members tickets cost $32.10 + HST, youth (3 to 14): $27.30 + HST. For adult members (15+), tickets cost $28.30 + HST and youth (3 to 14): $24.55 + HST.

To book tickets, click here.

8 Gays of Channukah

(Courtesy: gsiproductions/Instagram )

Gila Münster’s 5th Annual 8 Gays of Channukah Queer Jewish variety show is set to take place on Sunday, Dec. 17 at Longboat Hall. 

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The 8 Gays of Channukah started in 2019 in the city’s gay village. Now it is the biggest annual event in the queer Jewish calendar. This year, a full cast of eight performers, spanning drag queens, burlesque dancers, comics, singers and more promises a fabulous night of entertainment.

A portion of ticket sales will be donated to Machane Lev, Canada’s queer Jewish summer camp.

This is a 19+ event, tickets can be purchased here, starting at $18.

Toronto Zoo’s 12 Days of Enrichment

(Courtesy: thetorontozoo)

Starting on Dec. 27, the Toronto Zoo is hosting a 12-day series of interactive activities for its animal-loving guests. From carcass feeds with majestic lions to educational adventures with plant-loving herbivores!

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The Toronto Zoo is open throughout the holidays between 9:30 a.m and 4:30 p.m. 

Get your tickets here.

STACKT Holiday Hills

(Courtesy: stacktmarket/Instagram)

The Disco Mistletoe and Speakeasy Whiskey Bar has returned to STACKT for the holiday season along with a selection of immersive activations and retail experiences at its holiday market. 

Stroll a 120-ft. tunnel of lights with breathtaking city views, play a game of all-weather outdoor curling and cozy up in the warming huts between turns. Pick up a s’mores kit from the Fizz & Fire patio and toast to the holidays with a celebratory glass of bubbly from the bar. Round out your evening with seasonal offerings from Kong’s Hot Tacos, or warm winter baos from Baobird.

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For Stackt’s full list of events and holiday experiences, click here.

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