Fun Things To Do This Week (December 16-22)

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The countdown to Christmas is officially on. But are you too caught up in last-minute shopping or trying to decipher holiday recipes? It’s time to hit pause and experience festive vibes. This season only comes around once a year, so you shouldn’t miss the holiday events and activities happening in the city. Now, let’s check out these best things to do this week in Toronto (December 16-22).

Note: Details may be subject to change. Check the official website or social media platforms for the latest updates.

Fun Things To Do This Week in Toronto (December 16-22)

Holiday! An Improvised Musical (Ongoing, Until December 21)

Things To Do This Week (December 16-22)
Photo via @baddogtheatre and @factorytheatre / Instagram 

Love musicals but tired of the same old tunes? Holiday! is back for its second run, and it’s about YOUR ideas. Every night, the cast takes audience suggestions and turns them into a brand-new holiday-themed musical on the spot.

  • Location: Factory Theatre (125 Bathurst Street, Toronto)
  • Admission: Get your tickets here.
  • Website: www.factorytheatre.ca
  • Best for: Date night, friends, or those who want to be part of the creative chaos.

Winter Glow (Ongoing, Holiday at The WellUntil December 22)

Looking for a fun, festive night out? Winter Glow offers magical light displays and thrilling carnival rides. Try the 45-ft Ferris wheel or enjoy the twinkling lights all around. Feeling adventurous? Try the teacup rides or test your luck at the midway games.

  • Location: Sankofa Square (1 Dundas St E, Toronto)
  • Admission: Free. Ride tickets start at $6. 
  • Website: www.sankofasquare.ca
  • Best for: Families, friends, and anyone craving festive outdoor fun.

Winter Market at St. Lawrence Market (Ongoing, Until December 23)

Holiday shopping feels easier when it’s festive. At this cosy outdoor market, you’ll find local products, unique gifts, and tasty snacks. Stroll through the stalls at your own pace. Also, grab something warm to drink and enjoy live music while you shop.

Yorkville Village Holiday Pop-up Markets (Ongoing, Until December 23)

Need holiday gift inspiration? These pop-up markets showcase products from over 150 Canadian brands and makers. Browse jewellery, beauty products, baby toys, candles, and more. From holiday décor to specialty treats, you’ll discover something for everyone on your list.

  • Location: Yorkville Village (55 Avenue Rd, Toronto)
  • Admission: Free 
  • Website: www.yorkvillevillage.com
  • Best for: Stylish gift hunters, families, and festive hosting ideas.

LEGO Holiday Pop-Up Market (Ongoing, Until December 23)

Photo via @holidayfairto / Instagram 

Got LEGO fans in the family? This holiday pop-up features a life-size LEGO fireplace and interactive build stations. Kids (and kids at heart) can craft their own ornaments for a Christmas tree. Plus, grab a LEGO set for holiday gifting. Spend $35 and get a little bonus gift, too.

  • Location: Mel Lastman Square (5100 Yonge St, North York)
  • Admission: Free 
  • Website: www.fairinthesquare.ca
  • Best for: Families, LEGO lovers, and creative holiday activities.

Holiday Fair in the Square (Ongoing, Until December 23)

A festive wonderland of artisan shops, an outdoor Polar Point Bar, and a fireside lounge await you at this holiday fair. Plus, Santa’s Village is waiting for your best selfies. With roaming performers and food vendors galore, you’ll feel the festive cheer.

  • Location: Mel Lastman Square (5100 Yonge St, North York)
  • Admission: Free 
  • Website: www.fairinthesquare.ca
  • Best for: Families, friends, couples, or holiday market enthusiasts.

Ho, Ho, Haute! Santa is Back at Bayview Village (Ongoing, Until December 24)

Photo via @bvshops / Instagram 

Santa made Bayview Village his home again, and it’s extra fabulous this year. Book a photo session or drop by for a walk-in appointment. They even have sensory-friendly sessions with minimal lights and noise, making it accessible for everyone.

  • Location: Bayview Village Shops (2901 Bayview Avenue, Toronto)
  • Admission: Get your tickets here.
  • Website: www.bayviewvillageshops.com
  • Best for: Family photos, sensory-friendly holiday outings.

Ginger’s Cocktail Bar Pop-Up (Ongoing, Until December 24)

Holiday cocktails? This west-end pop-up serves creative drinks, seasonal treats, and some of the cutest holiday décor you’ve ever seen. Seriously, every corner is Insta-worthy.

  • Location: Le Dolci Culinary Classroom (12 Sousa Mendes, the Junction Triangle, Toronto)
  • Admission: Book your table here
  • Website: www.gingerscocktailbar.ca 
  • Best for: Cocktail lovers, friends, or those who enjoy festive aesthetics.

Miracle Toronto 2024 (Ongoing, Until December 29)

Things To Do This Week (December 16-22)
Photo via @miracletoronto and @hctrvqz  / Instagram 

At The Miracle Toronto? Expect over-the-top kitschy décor, a menu of holiday-inspired cocktails, and a lot of festive vibes. Also, snap a pic with Santa or sip on something merry while supporting Nellie’s Women’s Shelter.

  • Location: Third Place, 875 Bloor St W,  Toronto 
  • Admission: Reserve your table here.
  • Website: www.miracletoronto.com 
  • Best for: Festive drinkers, friends, or date nights.

Holiday Hills (Ongoing, Until December 29)

From live entertainment and light installations to curling lanes and fire pits, boredom has no place in Holiday Hills. You can shop over 100 local vendors or try some festive cocktails. And don’t miss the s’mores huts.

  • Location: STACKT Market (28 Bathurst Street, Toronto)
  • Admission: Free
  • Website: www.stacktmarket.com
  • Best for: Families, friend groups, and anyone looking for festive fun.

Festive Lights Double-Decker Bus Tour (Ongoing, Until December 30)

Want to experience Toronto’s holiday magic from the top of a double-decker bus? This 75-90 minute guided tour takes you past iconic landmarks like Nathan Phillips Square and Yorkville. The lights are dazzling, and the city feels alive with holiday spirit.

  • Location: The bus boards nightly on the east side of Yonge Street beside the Visitor Information kiosk at Sankofa Square (1 Dundas St E, Toronto)
  • Admission: Get your tickets here.
  • Website: www.citysightseeingtoronto.com
  • Best for: Tourists, date nights, and festive sightseeing.

Charlie and the Chocolate Factory (Ongoing, Until December 30)

Things To Do This Week (December 16-22)
Photo via @ypttoronto / Instagram 

Want to enter Willy Wonka’s world? You can do it with this whimsical musical adaptation of the classic Roald Dahl story. From chocolate rivers to Oompa Loompas, it’s a sugar rush for the imagination.

  • Location: Young People’s Theatre (165 Front St E, Toronto)
  • Admission: Get your tickets here.
  • Website: www.youngpeoplestheatre.org
  • Best for: Families, nostalgia seekers, and chocoholics.

Dinos Alive: An Immersive Experience (Ongoing, Until December 31)

Jurassic Park, who? This mesmerising experience brings the dinos to life. Life-sized replicas, a virtual aquarium, and even a hands-on paleontologist space make this educational and fun. Even the adults will feel like kids again.

  • Location: 30 Hanover Road, North York
  • Admission: Get your tickets here
  • Website: www.dinosaliveexhibit.com
  • Best for: Families and dinosaur fans of all ages.

Holiday at The Well (Ongoing, Until December 31)

Prefer a calmer holiday vibe? Holiday at The Well is a Nordic-inspired escape. Browse the Vendor Village, featuring local artisans and unique finds. Sip on a warm drink and enjoy the festive decorations.

  • Location: 486 Front St W, Toronto
  • Admission: Free 
  • Website: www.thewelltoronto.com
  • Best for: Quiet gift shopping, couples, and Nordic décor fans.

Daily Tree Light and Snow Shows (Ongoing, Until December 31)

Winter wonderland at the CF Toronto Eaton Centre? Watch daily light and snow shows that create magical holiday moments. It’s a simple yet mesmerising way to soak up the season. Bring friends or family—it’s an experience worth sharing.

  • Location: CF Toronto Eaton Centre (220 Yonge St, Toronto)
  • Admission: Free 
  • Website: www.shops.cadillacfairview.com
  • Best for: Families, casual hangouts, and holiday photo ops.

Naughty, Nice, & Undecided (Ongoing, Until December 31)

Bringing the fam for the “Nice” show or staying late for the “Naughty” version? Prepare for some side-splitting laughs. Can’t decide? That’s what the “Undecided” part is for. So, just come and enjoy the show.

  • Location: The Second City (The Second City, 110 Harbour St, Toronto)
  • Admission: Get your tickets here
  • Website: www.secondcity.com
  • Best for: Families (nice version), 19+ (naughty version), or comedy lovers.

Bloor-Yorkville Holiday Magic 2024 (Ongoing, Until December 31)

Things To Do This Week (December 16-22)
Photo via @blooryorkville / Instagram 

Haven’t strolled through Bloor-Yorkville during the holidays yet? It’s your chance this year. The sparkling lights lining the streets and urban campfire benches can make you feel like you are entering a winter fairy tale.

  • Location: Village of Yorkville Park (115 Cumberland Street, Toronto), Urban Campfire Benches – Bloor Street West (between Church Street and Avenue Road)
  • Admission: Free 
  • Website: www.bloor-yorkville.com
  • Best for: Couples, shoppers, and anyone who loves twinkling lights.

National Ballet of Canada: The Nutcracker (Ongoing, Until December 31)

Things To Do This Week (December 16-22)
Photo via @nationalballet and @karolinakuras / Instagram 

A holiday tradition that never gets old. The Nutcracker features breathtaking sets, elegant costumes, and world-class dancing. Is it your first time or your fifteenth? This timeless ballet is a must-see holiday performance.

  • Location: Four Seasons Centre for the Performing Arts (145 Queen Street West, Toronto)
  • Admission: Get your tickets here.
  • Website: www.national.ballet.ca
  • Best for: Families, friends, or ballet lovers.

Cirque Du Soleil – Twas The Night Before (December 12, 2024 – January 3, 2025)

Leave it to Cirque du Soleil to reinvent the holidays. This awe-inspiring show brings the classic “A Visit from Saint Nicholas” poem to life with jaw-dropping acrobatics and heartwarming storytelling.

  • Location: Meridian Hall (1 Front St E, Toronto)
  • Admission: Get your tickets here.
  • Website: www.cirquedusoleil.com
  • Best for: Families, friends, and Cirque fans.

Casa Loma Holiday Lights Tour (Ongoing, Until January 4, 2025)

Photo via @casalomatoronto / Instagram

Casa Loma gets a holiday glow-up every year. You can wander through the magical light displays, explore the decorated gardens, and catch live performances. And say hi to Santa in his workshop—he’s waiting.

  • Location: Casa Loma (1 Austin Terrace, Toronto)
  • Admission: Check ticket prices here
  • Holiday Lights VIP Experience (Admits 2): December 1 – Dec 19 ($125), December 20 – January 4 ($150) 
  • Website: www.casaloma.ca
  • Best for: Families, couples, and anyone who loves holiday lights.

Holiday Nights of Lights (Ongoing, Until January 4, 2025)

Photo via @nightsoflightsto and @photobyjass.ca / Instagram 

A light show during the holiday season? This event features over 1.5 million LED lights synced to holiday tunes. Add food trucks, interactive displays, and a market; you’ll get the perfect holiday hotspot.

  • Location: Upper Canada Mall 17600 Yonge St. Newmarket, ON
  • Admission: Get your tickets here.
  • Website: www.nightsoflights.ca
  • Best for: Families, couples, or friends.

Distillery Winter Village (Ongoing, Until January 5, 2025)

The Distillery Winter Village’s cobblestone streets, twinkling lights, and mulled wine capture what it feels like to be on a Christmas postcard. Don’t miss the picture-perfect Christmas tree, the seasonal vendor cabins, live entertainment, and delicious food.

  • Location: Distillery District (55 Mill Street, Toronto)
  • Admission: $15 General Admission, $18 Flex Ticket, $30 Express Gate Entry, $39.50 Combo Ticket. Free for those aged nine and under. Get your tickets here.
  • Note: Tickets are required Thursday to Sunday after 4:00 PM, daily from December 12 – December 31 after 4:00 PM
  • Website: www.thedistillerywintervillage.com
  • Best for: Romantic dates and festive family outings.

The Wizard of Oz: The Toto-ly Awesome Family Musical (Ongoing, Until January 5, 2025)

Photo via @canadianstage / Instagram

Dorothy, Toto, and the gang are back with plenty of jokes, toe-tapping tunes, and larger-than-life characters. This pantomime revival offers a perfect mix of nostalgia and holiday fun.

  • Location: The Elgin and Winter Garden Theatre Centre (189 Yonge Street, Toronto)
  • Admission: Get your tickets here.
  • Website: www.canadianstage.com
  • Best for: Families and anyone who loves a good laugh.

AGO Holiday Afternoon Tea (Ongoing, Until January 5, 2025)

Need a festive tea break? The AGO offers a holiday afternoon tea experience where you can sip delicious teas and enjoy a curated menu. Also, the gorgeous surroundings of the Norma Ridley Members’ Lounge.

  • Location: The Grange, Art Gallery of Ontario (317 Dundas St W, Toronto)
  • Admission: Book your table here.
  • Website: www.ago.ca
  • Best for: Tea lovers and those craving a sophisticated holiday treat.

Winterfest Toronto (Ongoing, Until January 5, 2025)

The whole vibe of Harbourfront Centre during Winterfest? You’ll love the sparkling lights, a walk-in Christmas tree, and a sugar shack. Also, you can snack on treats from food trucks and enjoy live entertainment by the fire pit.

  • Location: Harbourfront Centre (235 Queens Quay West, Toronto)
  • Admission: Free 
  • Website: www.winterfesttoronto.com
  • Best for: Foodies, families, friends, and couples.

Cavalcade of Lights (Ongoing, Until January 7, 2025)

Photo via @kevin.braganza / Instagram 

The Cavalcade of Lights is Toronto’s ultimate winter glow-up, featuring the city’s official Christmas tree lighting, light displays, and live performances. Also, try the nightly ice skating, a perfect excuse to dust off your skates (or rent a pair) and glide under the stars.

  • Location: Nathan Phillips Square (100 Queen St W, Toronto)
  • Admission: Free
  • Website: www.toronto.ca
  • Best for: Holiday vibes, festive date nights, or family fun.

FHPZ Holiday Tree (Ongoing, Until January 4, 2025)

High Park Zoo turns into a wonderland of decorated trees, each uniquely adorned by generous sponsors. Stroll along the Snowflake Walk and admire the twinkling lights while enjoying a festive atmosphere. Plus, you can join the fun by sponsoring and decorating your very own tree.

  • Location: High Park Zoo (1873 Bloor St West, Toronto)
  • Admission: Free 
  • Website: www.highparkzoo.ca  
  • Best for: Families and nature lovers.

New Vistas Art Exhibition (Ongoing, Until January 14, 2025)

Feeling artsy? The New Vistas Art Exhibition offers fresh perspectives and bold ideas. Stroll through thought-provoking pieces that might just spark your own creativity. Perfect for anyone looking to break away from the usual holiday routine.

  • Location: Etobicoke Civic Centre Art Gallery, 399 The West Mall, Toronto 
  • Admission: Free 
  • Website: www.toronto.ca
  • Best for: Art lovers, cultural day trips, and solo outings.

Window Wonderland (Ongoing, Until January 31, 2025)

Window Wonderland features 20 augmented reality (AR) window displays and 10 stunning murals celebrating local talent. Just grab your phone and snap some Instagram-worthy pics.

  • Location: The Junction neighbourhood
  • Admission: Free 
  • Website: www.torontojunction.ca
  • Best for: Art enthusiasts, friends, or casual strollers

Union Winter 2024 Presented by TD (Ongoing, Until February 2, 2025)

Photo via @torontounion and @rawcoh / Instagram 

Switch things up this winter with a visit to Union Winter’s roller rink. They’ve got free skate rentals, beginner lessons, and live DJ sets. A seasoned skater or just here for the vibes? This spot delivers holiday fun in a cool, unique way.

  • Location: Union Station (55 Front St W, Toronto)
  • Admission: Free. Register here
  • Website: www.torontounion.ca
  • Best for: Friends, music lovers, and active holiday hangouts.

Cocktails & Candy Canes 2024 (December 16)

Photo via @torontomusicalconcerts / Instagram 

Spend an evening with Toronto’s most talented musical theatre artists. The Cocktails & Candy Canes concert offers a mix of jazz, gospel, and holiday classics. Also, sip on festive drinks and enjoy a night of pure entertainment.

  • Location: Hugh’s Room Live (296 Broadview Avenue, Toronto)
  • Admission: Get your tickets here
  • Website: www.torontomusicalconcerts.com
  • Best for: Music lovers, date nights, and festive soirées.

Illumination: Cozy Sundays at Spadina Museum (December 16)

Photo via @tohistorymuseums / Instagram 

Ready to step back into the 1920s holiday season at the Spadina Museum? Here, you can explore the mansion, decked out in vintage holiday decorations. Smell the cedar garlands, listen to nostalgic tunes, and grab cider and cookies from the gift shop.

  • Location: Spadina Museum (285 Spadina Rd, Toronto)
  • Admission: Free 
  • Website: www.toronto.ca
  • Best for: History buffs, families, and low-key festive outings.

Christmas Karaoke Pop-Up (December 16–17)

At the Christmas Karaoke, you can show off your singing skills, compete in an ugly sweater contest, or enjoy specialty cocktails. It’s two nights of holiday cheer with great food and fun prizes.

  • Location: Lodge On Queen (251 Queen St W, Toronto)
  • Admission: Get your tickets here.
  • Instagram: @lodgeonqueen 
  • Best for: 19+, friends, karaoke fans, and casual festive gatherings.

Toronto Performance Night Theatre Festival 2024 (December 17–19)

Toronto Performance Night highlights the richness of Persian performing arts. This cultural celebration lets you experience heartfelt stories and incredible performances.

  • Location: Fairview Theatre (35 Fairview Mall Dr, North York)
  • Admission: Get your tickets here.
  • Website: www.tpnight.ca 
  • Best for: Theatre lovers and cultural explorers.

Scott Helman (December 18)

Photo via @scotthelman and @liapappaskemps / Instagram 

Catch Toronto’s own Scott Helman in concert. His folk-pop sound is packed with heart, and his lyrics hit home. And it doesn’t matter if you’re a fan or new to his music; this show promises an intimate and memorable evening.

  • Location: The Axis Club (722 College St, Toronto)
  • Admission: Get your tickets here
  • Website: www.scotthelmanmusic.com
  • Best for: Music lovers, casual concert nights, and fans of local talent.

Holiday Social Charity Event: Casino Royale (December 19)

As you join this holiday event, you can enjoy casino games, live entertainment, and scotch tastings while giving back to the community. It combines glamour and generosity for a fun night.

  • Location: Lavelle (627 King Street West, Toronto)
  • Admission: Get your tickets here
  • Website: www.thehiphaus.com
  • Best for: Glam nights out, charity supporters, and 19+ events.

KESmas – Kes The Band Live in Concert (December 19)

Kes The Band is bringing the party vibes this December! This Trinidadian soca group, formed in 2005, is known for their addictive blend of R&B, EDM, rock, pop, Soca, and reggae. Are you into tropical beats or just love live music? This concert is a must-see.

  • Location: History (1663 Queen St E, Toronto)
  • Admission: Get your tickets here
  • Website: www.kestheband.com
  • Best For: Fans of energetic Caribbean vibes and eclectic live music experiences.

Down With Webster (December 20 – 21)

This week, catch Down With Webster, Toronto’s genre-defying band that mixes rap, rock, and pop. Known for their high-energy shows, they’ll get you moving with every beat. So, prepare to experience their electric vibe live.

  • Location: History (1663 Queen St E, Toronto)
  • Admission: Get your tickets here (Dec 20) or here (Dec 21).
  • Website: www.thecbpshop.com
  • Best For: Those who love high-energy concerts with genre-blending music.

Hangar Skate Returns to YZD! (December 20, 2024 – February 17, 2025)

Photo via YZD 

Winter at YZD means skating fun for everyone. Enjoy the 4,500-square-foot refrigerated rink surrounded by stunning art installations. This event offers free admission, affordable skate rentals, DJ nights, and arts programming for all ages.

  • Location: YZD (34 Hanover Road Toronto)
  • Admission: Free. RSVP here.
  • Website: www.yzd.ca
  • Best For: Families, date nights, or anyone who loves outdoor skating.

A Very Bettys Christmas – Old Mill Toronto Jazz Lounge (December 20)

Photo via @oldmilltoronto and @thebettysband / Instagram 

Known for their sultry harmonies and vintage charm, The Bettys will perform holiday classics with a clever twist. It’s the perfect mix of festive music, playful humour, and retro style. So, dress to impress and enjoy a cosy, music-filled evening.

  • Location: Old Mill Toronto (21 Old Mill Road, Toronto)
  • Admission: Get your tickets here
  • Website: www.oldmilltoronto.com
  • Best For: 19+, fans of vintage jazz vibes, holiday classics, and charming live performances.

Bloorcourt Holiday Night Light Walk (December 20)

Photo via @bloorcourt, @smkasman and @bestofbloor / Instagram

Love exploring holiday lights? Join the Bloorcourt Holiday Night Light Walk, led by local artist Shari Kasman. You’ll visit beautifully lit streets and businesses, so wear your warmest coat and comfortable shoes. This event also supports the Oasis Dufferin Food Bank.

  • Location: Bloorcourt Area – Meet at 977 Bloor St W (African Palace), Toronto
  • Admission: Get your tickets here.
  • Instagram: @bloorcourt 
  • Best For: Families, photography enthusiasts, and anyone who loves holiday lights and cosy walks.

A Glow-in-the-Dark Paint Night by Artbox (December 20)

Photo via @artboxstudiogallery / Instagram 

Joining Artbox’s Glow-in-the-Dark Paint Night? You can sip a drink and bring out your creativity. Feeling stuck? No worries, Natasha’s there to help.

  • Location: Artbox Studio Gallery (1226 Kingston Rd, Toronto)
  • Admission: Get your tickets here
  • Website: www.artboxstudiogallery.com
  • Best for: A creative night out with friends or a unique date.

Elvis – A Christmas Special with Pete Paquette (December 20)

How about a holiday trip down memory lane with Pete Paquette’s electric tribute to Elvis Presley? From “Blue Christmas” to classic carols, this show offers a festive vibe with a rock ‘n’ roll twist.

  • Location: The Theatre at Great Canadian Casino Resort (1133 Queens Plate Dr, Toronto)
  • Admission: Get your tickets here
  • Website: www.paquetteproductions.com
  • Best for: Music lovers and Elvis fans.

Maker Friday: The Culture (December 20)

Get crafty with a hip-hop twist. This free pop-up at the AGO lets you design and customise sneaker laces while vibing to the energy of the exhibition The Culture: Hip Hop and Contemporary Art.

  • Location: Art Gallery of Ontario (317 Dundas St W, Toronto)
  • Admission: Included in General Admission 
  • Website: www.ago.ca
  • Best for: Sneakerheads and friends.

Mike Rita Live at The Paradise Theatre (December 20)

Need a good laugh? Mike Rita is bringing his signature “420 Ethnic comedy” to The Paradise Theatre. From jokes about everyday life to stories that’ll make you laugh till you cry, his act is a rollercoaster of relatable hilarity.

  • Location: Paradise Theatre (1006c Bloor Street West Toronto)
  • Admission: Get your tickets here or here.
  • Website: www.paradiseonbloor.com
  • Best for: 19+, friends, couples, comedy lovers, and anyone who needs a night of laughs.

Winter Bloom (December 20–22)

Photo via @tbg_canada / Instagram 

Winter Bloom combines aerial silks, acrobatics, and heartwarming humour to create a fun, interactive experience for all ages. As a bonus, you can snap a selfie with the performers afterward.

  • Location: Toronto Botanical Gardens (777 Lawrence Avenue East Toronto)
  • Admission: Get your tickets here.
  • Website: www.torontobotanicalgarden.ca
  • Best for: Family outings, friends, or circus enthusiasts.

Aryana Sayeed (December 21)

Experience the powerful voice of Aryana Sayeed, an Afghan pop singer. She blends Dari Persian, Pashto, and Uzbek influences to create music that speaks to the soul. Don’t miss this chance to see her perform live and connect with her artistry.

  • Location: Great Canadian Casino Resort Toronto (1133 Queens Plate Dr., Toronto)
  • Admission: Get your tickets here.
  • Website: www.aryanatour.com
  • Best For: Fans of world music and powerful, socially conscious performances.

Retro Market (December 21)

At the Retro Market? Vintage lovers can find everything from Y2K fashion to home décor. Shop handmade jewellery and art prints, and even enjoy live portraits. Warm up with cookies and hot drinks while feeling the nostalgic vibe.

  • Location: Youthful Vengeance (1110 Dundas St W, Toronto)
  • Admission: Free 
  • Instagram: @retromarket.ca
  • Best For: Vintage lovers, holiday shoppers, and anyone looking for unique finds.

Winter Skating at The Bentway (December 21, 2024–February 17, 2025)

Photo via @thebentway and @joanna.roselli / Instagram 

Skating under the Gardiner Expressway? The Bentway’s 220m figure-eight skate trail is back and welcomes pros and those who are just learning. Also, keep an eye out for free skate rental nights.

  • Location: 250 Fort York Blvd, Toronto 
  • Admission: Free 
  • Website: www.thebentway.ca
  • Best for: Skaters of all levels and winter enthusiasts.

Westfall’s World: Twelve Tricks of Christmas (December 21–22)

Photo via TYT Theatre 

Holiday magic, literally. This interactive show is beyond impressive tricks; it creates memorable holiday moments. Westfall’s mix of humour, magic, and audience participation will have you grinning from ear to ear.

  • Location: Wychwood Theatre (76 Wychwood Ave studio 176, Toronto)
  • Admission: Get your tickets here.
  • Website: www.tyttheatre.com
  • Best for: Families and anyone who loves a good magic show.

Reid’s Christmas Market (December 21)

Reid’s Christmas Market has everything to complete your shopping list, including handmade gifts and unique finds. You can also enjoy yummy treats, hot chocolate, or festive cocktails.

  • Location: Reid’s Distillery (32 Logan Avenue, Toronto)
  • Admission: Free
  • Website: www.reidsdistillery.com  
  • Best for: Last-minute shoppers and holiday enthusiasts.

The Very Very UGLY EMO CHRISTMAS Sweater Party (December 21)

Photo via @nickel9distillery, @eyes_like_static, and @the.overtones / Instagram 

Break out your cringiest emo sweater and prepare to rock. This pop-punk event is a nostalgia party with live music, themed drinks, and prizes for the “best” ugly sweater.

  • Location: Nickel 9 Distillery (90 Cawthra Ave Unit 100, Toronto)
  • Admission: Get your tickets here.
  • Website: www.nickel9distillery.com
  • Best for: Emo fans and anyone who loves a quirky night out.

Breakfast with Santa & Mrs. Claus (December 21–22)

Photo via @hotelxtoronto / Instagram 

Start your morning with pancakes and holiday cheer. Santa and Mrs. Claus are making a special appearance at Hotel X Toronto, complete with crafts, surprises, and photo ops.

  • Location: Hotel X Toronto (111 Princes’ Boulevard, Toronto)
  • Admission: Reserve your spot here.
  • Website: www.blog.hotelxtoronto.com
  • Best for: Families with young kids.

Sing-Along Messiah (December 22)

Photo via Tafelmusik 

Join the holiday tradition at Massey Hall’s Sing-Along Messiah. Experience Handel’s masterpiece with a live orchestra and 2,000 voices. This year marks the event’s debut in Massey Hall’s renovated space. It’s a perfect mix of festive spirit and timeless music.

  • Location: Massey Hall (178 Victoria Street, Toronto)
  • Admission: Get your tickets here.
  • Website: www.tafelmusik.org
  • Best For: Fans of classical music, holiday traditions, and large, joyful community events.

Winter Market at Evergreen Brick Works (December 22)

Sundays get festive at Evergreen Brick Works. This winter market is your go-to for handmade gifts, vintage finds, and interactive workshops. You can also sip hot cocoa and toast some s’mores by the fire.

  • Location: Evergreen Brick Works (550 Bayview Ave, Toronto)
  • Admission: Pay-What-You-Can (suggested donation of $5)
  • Website: www.evergreen.ca
  • Best for: A laid-back Sunday or finding unique holiday gifts.

Matt Rogers – The Prince of Christmas Tour (December 22)

Photo via @mattrogerstho / Instagram 

Wish to combine comedy and pop culture with holiday vibes? Matt Rogers will do that for you. Known for his witty takes on entertainment, his tour is a fun mix of laughs and holiday spirit.

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