December 30 to January 1

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Written By
Erin Nicole Davis

As we enter the last weekend of the year, some prefer to lay low and reflect, while others would rather get out and take full advantage of the long weekend — one that straddles 2022 and 2023. 

For those looking to hit the town, Toronto is making up for lost time this year, with a slew of celebrations throughout the city for people of all ages and interests. 

From live music to a high-profile comedy show, here’s what’s happening in Toronto this weekend. 

LOL in Real Life at the Dave Chapelle Show 
Kick off the New Year with laughter and swap the Dave Chapelle Netflix specials for the real deal. The famed comedian hits Scotiabank Area on Sunday, January 1 as part of his highly anticipated In Your Dreams Tour. Find more info here

Brave the Grip of Winter with a Polar Bear Dip
Those looking to dive into 2023 on a refreshing(?) note can join hundreds of others in the city’s annual Polar Bear dip at Sunnyside Park for a noon-hour dip in Lake Ontario on Sunday morning. Tickets cost $30, with all proceeds benefitting Boost Child & Youth Advocacy Centre. Find more info here

Hit a Masquerade Ball at Toronto’s Hottest New Hotel 
The Ace Hotel Toronto will mark its first New Year’s Eve in the city with a masquerade ball at its newly opened fourth floor spot, Evangeline. Guests can expect a night of music, dancing, art, food, and cocktails as they mingle with sophisticated party revellers in the design-forward space. Find more info here.

Rock Your Best Black and White and Hit the Beach
Over in the east end, the Toronto Beach Club will host its annual Black & White Ball this New Year’s Eve. The glamorous affair will take over the venue, with three DJs spinning three different sounds in three rooms. Find more info here

Revisit the 80s with a Scenic Bash 
Rooftop spot Harriet’s is inviting the city’s well-heeled set to don their most glamorous Studio 54 outfits and ring in the New Year with a backdrop of Toronto. Guests can expect talented DJs, opulent sushi boats, and bottle service. Find more info here.

Channel Your Inner Ross or Rachel at the Friends Experience 
Combine Boxing Week shopping at Yorkdale with a world of nostalgic Instagram ops at The Friends Experience: The One in Toronto. The immersive exhibit invites guests to explore set recreations, like Joey and Chandler’s apartment, Monica and Rachel’s kitchen, and Central Perk. Find more info here

Kiss the Holiday Season Goodbye in a Winter Wonderland 
This weekend marks the last time you can check out the Distillery Winter Village before it packs up for the season. The crowd-drawing affair fills the historic Distillery District with holiday-themed eats and drinks, festive vendors, and no shortage of photo ops – including a towering Christmas tree sponsored by Dior. Find more info here

Immerse Yourself in a World of Disney
Step inside an immersive world of all things Disney at the just-opened Disney Animation: Immersive Experience. The memorable experience showcases Disney Animation Studios’ rich and nostalgic history, as guests can relive everything from a magic carpet ride to going under the sea. Find more info here

Stroll Through a Festive Shipping Container Marketplace 
This weekend marks the last of Stackt Market’s Holiday Hills festive winter wonderland. The shipping container marketplace is jam-packed with food and drinks, festive activities, fire pits, interactive installations, and even a fire pit. Find more info here.

Sing Along to the Sounds of Toronto’s Best Cover Band 
Beloved Canadian cover band Dwayne Gretzky will take the stage at History this New Year’s Eve. The annual event makes for a high-energy affair of flowing drinks and singing and dancing along to mind-blowing renditions of hits from today and times past. Find more info here

Soak in the Nostalgia of Joseph and the Amazing Technicolor Dreamcoat 
The beloved musical Joseph and the Amazing Technicolor Dreamcoat — a smash-hit in the ’90s — has returned to Toronto. The brand new production of Tim Rice and Andrew Lloyd Webber’s musical made its North American premiere at the Princess of Wales Theatre on Sunday. Find more info here.

Ring in the New Year with a Sky Full of Fireworks 
Ring in 2023 with a bang with what promises to be a dazzling downtown fireworks display. Come midnight on January 1, the sky above Toronto’s waterfront will be illuminated by two synchronized fireworks displays. Find more info here

Written By
Erin Nicole Davis

Erin Nicole Davis is a born and raised Toronto writer with a passion for the city and its urban affairs and culture.

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