Fun Things to Do in Toronto This Week (December 8-14 Holiday Guide)
Some weeks just feel like they’re begging for a little extra fun, and this one is definitely in that zone. As the city settles into that pre-holiday buzz where everyone’s juggling errands, social plans, and “just one more” event, this guide to things to do in Toronto this week (December 8-14) makes the search a whole lot easier. And since plans don’t always stay within Toronto limits, I’ve also added a few fun options just outside the city in case you’re up for a little winter wander.
Event details often change, so check official pages before you go. Remember: Free entry may still require an RSVP or extra payment for food, drinks, and activities.
Free Things To Do
Guess? Warehouse Sale
If your winter wardrobe feels a little too basic, this sale might be your moment. You’ll find racks of discounted Guess? pieces and more, which makes browsing surprisingly fun even if you “only came to look.”
- When: December 10-14, 2025
- Where: The International Centre (6900 Airport Road, Mississauga)
- Tickets: Free admission
- Website: https://www.premiumretailgroup.com
- Best for: Shoppers hunting solid deals.
Winter Glow
Sankofa Square lights up again with music, installations, and a festive atmosphere that feels lively without being overwhelming. The event runs evenings on weekdays and longer on weekends, making it easy to fit into your schedule.
- When: December 11-21, 2025
- Where: Sankofa Square (1 Dundas St. E., Toronto)
- Tickets: Free admission
- Website: https://www.sankofasquare.ca
- Best for: After-work or weekend holiday plans.
Riverside Window Wonderland
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More than 25 holiday windows designed by local artists line Queen St. E. Visit, vote, and explore as you support local businesses along the way.
- When: Until December 10, 2025
- Where: Storefronts along Queen E from Davies to De Grassi St
- Tickets: Free admission
- Website: https://riverside-to.com
- Best for: A quick neighbourhood stroll.
Winterfest Toronto 2025
Harbourfront Centre turns into a festive hub with lights, markets, train rides, a new Winter Maze, and multiple performances. It’s easy to spend a few hours wandering and enjoying the atmosphere.
- When: Until December 21, 2025
- Where: Harbourfront Centre (235 Queens Quay W., Toronto)
- Tickets: Free admission (select activities ticketed)
- Website: https://harbourfrontcentre.com
- Best for: Families wanting a full holiday outing.
Holiday Hills 2025
Expect holiday displays, comfort food, seasonal drinks, one-of-a-kind shops, and weekly entertainment. It’s a relaxed way to spend time outdoors with friends or family.
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- When: Until December 28, 2025
- Where: STACKT market (28 Bathurst St, Toronto)
- Tickets: Free admission
- Website: https://stacktmarket.com
- Best for: Casual weekend plans.
Holiday at The Well
The Well offers a Nordic-inspired outdoor setup with vendors, seasonal programming, and an open-air layout that feels spacious and easy. It’s a good stop for quick gifts and warm drinks.
- When: Until December 28, 2025
- Where: 486 Front St W, Toronto
- Tickets: Free admission
- Website: https://thewelltoronto.com
- Best for: Holiday shopping with fresh air.
Bloor-Yorkville Holiday Magic
Tree-lined streets glow with lights while Victorian carolers stroll and sing. The Urban Campfire Benches also light up in holiday colors, adding a playful touch along Bloor Street.
- When: Until December 31, 2025
- Where: Village of Yorkville Park (115 Cumberland Street & Bellair Street, Toronto)
- Tickets: Free admission
- Website: https://www.bloor-yorkville.com
- Best for: An evening walk after dinner.
Nathan Phillips Square Cavalcade of Lights
Skate, enjoy glowing installations, and catch cultural performances across the square. It’s one of Toronto’s easiest ways to feel the season without planning too much.
- When: Until January 7, 2026
- Where: Nathan Phillips Square (100 Queen St W, Toronto)
- Tickets: Free admission
- Website: https://www.toronto.ca
- Best for: Low-effort holiday outings.
TD Union Winter
Union Station hosts free roller skating, free lessons, DJ nights, live performances, and 19+ mixers. It’s a fun mix of music, movement, and winter energy right downtown.
- When: Until January 18, 2026
- Where: Union Station (65 Front St. W., Toronto)
- Tickets: Free admission (Advance registration for Roller Express recommended)
- Website: https://torontounion.ca
- Best for: Skaters and curious beginners
Paid & Ticketed Events
Oriental Legend Toronto Show
This grand dance drama makes its Canadian debut with powerful choreography, cinematic staging, and an emotional story set along the Silk Road. You’ll follow characters who grow from rivals into lifelong allies through vivid dance and rich visual design.
- When: December 12-13, 2025
- Where: The Elgin and Winter Garden Theatre (189 Yonge Street, Toronto)
- Tickets: Click here.
- Best for: Fans of cultural performances.
Breakfast with Santa at Hotel X Toronto
Hotel X brings back its festive breakfast with Santa, complete with a gourmet buffet, story time with Mrs. Claus, and crafts for kids. The waterfront lounge makes the morning feel extra special, and every child leaves with a keepsake gift.
- When: December 13-21, 2025
- Where: 111 Princes’ Blvd, Toronto
- Reservations: Click here.
- Website: https://www.hotelxtoronto.com
- Best for: Families who love holiday traditions.
Village Wonderland
Train rides, Santa photos, cookie decorating, and a community market fill the day with simple holiday fun. It’s cheerful, relaxed, and a nice way to support programs helping kids across Ontario.
- When: December 14, 2025
- Where: Variety Village (3701 Danforth Avenue, Toronto)
- Tickets: Click here.
- Website: https://varietyontario.ca
- Best for: A wholesome afternoon with family.
JR De Guzman: Boyfriend Material
JR blends comedy and music in a way that feels easy and personal. His international credits speak for themselves, but seeing him live brings an extra level of charm.
- When: December 14, 2025
- Where: Queen Elizabeth Theatre (190 Princes’ Blvd, Toronto)
- Tickets: Click here.
- Website: https://jrdeguzman.com
- Best for: A laid-back comedy night.
Winter Market at Evergreen Brick Works
Warm up by the fire with food and drinks, enjoy live entertainment, and explore workshops like pasta-making, candle crafting, and DIY skincare. It’s cozy and creative without being crowded.
- When: December 14 & 21, 2025
- Where: 550 Bayview Ave, Toronto
- Tickets: $5 suggested donation
- Website: https://www.evergreen.ca
- Best for: Hands-on holiday activities.
Ho, Ho, Haute! Santa at Bayview Village
Bayview Village brings back its stylish Santa setup under the chandelier. Kids get their photos, parents get a smooth holiday errand stop, and everyone leaves smiling.
- When: Until December 24, 2025
- Where: Bayview Village Shopping Centre (2901 Bayview Avenue, Toronto)
- Reservations: Click here.
- Website: https://www.bayviewvillageshops.com
- Best for: Holiday photos without chaos.
Miracle on Bloor Christmas Bar 2025
Third Place transforms into a festive adult playground with themed cocktails, drag shows, DJs, and holiday snacks. The décor goes big, making it a fun spot for a winter night out.
- When: Until December 29, 2025
- Where: 875 Bloor St. West, Toronto
- Reservations: Click here.
- Website: https://www.miracletoronto.com
- Best for: Friends who enjoy seasonal pop-up bars.
National Ballet of Canada: The Nutcracker
James Kudelka’s beloved production follows siblings Marie and Misha through a magical journey filled with creatures, treats, and Tchaikovsky’s iconic score. Thirty years later, it still feels special.
- When: Until December 31, 2025
- Where: Four Seasons Centre for the Performing Arts (145 Queen Street West, Toronto)
- Tickets: Click here.
- Website: https://national.ballet.ca
- Best for: A traditional holiday night out.
Christmas at the Castle & Holiday Lights
Stroll through tunnels, gardens, and outdoor paths filled with glowing displays and seasonal performances. It’s self-guided, so you can take your time exploring.
- When: Until January 3, 2026
- Where: 1 Austin Terrace, Toronto
- Tickets: Click here.
- Website: https://casaloma.ca
- Best for: Scenic evenings with family or friends.
The Distillery Winter Village
The cobblestone streets fill with local artisans, holiday treats, romantic lighting, and great photo spots. It’s one of Toronto’s most popular seasonal outings for a reason.
- When: Until January 4, 2026
- Where: 55 Mill Street, Toronto
- Tickets: Only required during specific peak periods. Click here. Entry is free at all other times.
- Website: https://www.thedistillerywintervillage.com
- Best for: Friends, family, or date nights.
WinterFest at Canada’s Wonderland
Skate on Snow Flake Lake, enjoy live shows, ride select attractions, and wander through themed areas packed with lights and trees. It’s bright, busy, and fun for all ages.
- When: Until January 3, 2026
- Where: 9580 Jane St, Vaughan
- Tickets: Click here.
- Website: https://www.canadaswonderland.com
- Best for: Full-day holiday adventures.
Concerts
Mac DeMarco
Mac brings his relaxed “blue wave” sound to Toronto for one night. Fans know his shows feel casual yet memorable.
- When: December 8-9, 2025
- Where: Massey Hall (178 Victoria St, Toronto)
- Tickets: Click here.
- Website: https://www.macdemarco.com
- Best for: Indie music lovers.
Christmas With The Tenors Tour
The Tenors blend classical and pop with powerful harmonies. Expect originals, covers, and holiday favourites performed with rich vocals.
- When: December 8, 2025
- Where: Roy Thomson Hall (60 Simcoe St, Toronto)
- Tickets: Click here.
- Website: https://www.tenorsmusic.com
- Best for: Fans of vocal groups.
TSO Holiday Pops
The Toronto Symphony Orchestra performs festive classics with guest conductor Sarah Hicks and vocalist Mikaela Bennett. A carol singalong adds a warm, nostalgic touch.
- When: December 10-11, 2025
- Where: Roy Thomson Hall (60 Simcoe St, Toronto)
- Tickets: Click here.
- Website: https://www.tso.ca
- Best for: Families who enjoy orchestral holiday music.
Baroque and Beyond: Holiday Treats
Sinfonia Toronto offers a program that jumps from Handel to modern Canadian compositions. The Ezra Duo joins for a lively Mendelssohn concerto.
- When: December 11, 2025
- Where: Trinity-St. Paul’s Centre (427 Bloor Street West, Toronto)
- Tickets: Click here.
- Website: https://www.sinfoniatoronto.com
- Best for: Classical music fans.
Songs of the Season: Nostalgic Movie Moments
The Toronto Children’s Chorus performs songs from classic holiday films plus traditional carols. It’s sweet, familiar, and perfect for families.
- When: December 14, 20025
- Where: Roy Thomson Hall (60 Simcoe St, Toronto)
- Tickets: Click here.
- Website: https://roythomsonhall.mhrth.com
- Best for: Kids and adults who love holiday movie music.
Other Events/Activities to Check Out
- Mississauga Festival of Trees – Until December 14 at CreativeHub 1352 at Small Arms Inspection Building (1352 Lakeshore Road East, Mississauga) | PWYC
- Holiday Bricktacular – Until December 24 at LEGOLAND Discovery Centre (1 Bass Pro Mills Drive, Vaughan) | Ticketed
- EPOCH Bar & Kitchen Terrace Holiday Market – Until December 31 at The Ritz-Carlton (181 Wellington Street West, Toronto) | Free admission
- Toronto Maple Leafs Games – December 8, 11, & 13 at Scotiabank Arena (40 Bay St., Toronto) | Ticketed
- David Tao – Soul Power II World Tour – December 13 at Coca-Cola Coliseum (19 Nunavut Rd, Toronto) | Ticketed
Want something calm after all the busy holiday plans?
If you need a quieter moment between holiday events, candlelit concerts offer the perfect break. Warm lighting, beautiful music, and an intimate setting keep things simple but still special. I put together my guide to Candlelight Concerts in Toronto to help you find this season’s tributes and holiday shows.
More…
- https://www.overheretoronto.com/things-to-do-in-toronto-december-2025
- https://www.toronto.ca/explore-enjoy/festivals-events/festivals-events-calendar
- https://www.destinationtoronto.com/events
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