The holiday season in Toronto offers a wonderful mix of music, lights, art, and atmosphere. Here are five standout events happening around the city this year — perfect for date-nights, family outings, or simply soaking in the season. And, of course, at TotallyTorontoArt we’ll show you how to bring home the memories (or the art!) afterwards.
1. The Cathedral Church of St. James – “Messiah” at Christmas
Kick off your season with something deeply uplifting: the annual performance of Messiah at the Cathedral Church of St. James on Saturday December 13, 2025 at 7:30 pm (stjamescathedral.ca)
Expect majestic architecture, soaring choirs, and the famous “Hallelujah” chorus — an ideal way to bring art, music, and sacred-space together.
Pro tip: Arrive early to pick a seat where you can take in the full architecture and acoustics. Afterwards, stop by TotallyTorontoArt to pick up a piece capturing cathedral arches or choir scenes — imagine it as wall art to extend the magic.
2. Massey Hall – The Andrew Kim Christmas Show & more
For something a little more festive and grand-scale in a classic venue, head to Massey Hall. On Dec 3, 2025, the 21st Annual Andy Kim Christmas Show will light up the hall (ticketmaster.ca)
Don’t miss other seasonal concerts there too — with top Canadian artists, great venue acoustics, and the holiday spirit in full tilt. (masseyhall.mhrth.com)
Art-tie-in: After the show, browse TotallyTorontoArt for prints of Massey Hall’s historic interior, or music-themed art — perfect for music lovers or as a unique gift.
3. Cavalcade of Lights at Nathan Phillips Square
If you’re looking for magical lights, outdoor skating, and festive installations, this is it. The event runs from late November through early January at Nathan Phillips Square, and includes the official tree-lighting, interactive light installations, and nighttime skating beneath the city-lights. (toronto.ca)
Why it’s great: It’s free, it’s downtown, it’s festive — and you can pair it easily with browsing art in a warm café afterwards. At TotallyTorontoArt, consider a print of the illuminated square or rink scene to bring the winter glow home.
4. Winterfest at Harbourfront Centre
For a waterfront twist on holiday fun, Winterfest at Harbourfront Centre (Nov 28–Dec 31, 2025) brings lights, a winter maze, train rides, music, and craft markets along the lakeside. (harbourfrontcentre.com)
Good for: Families, couples, or anyone wanting a more relaxed festive outing — maybe pair with a hot chocolate, an art stop, and some lakeside charm. At TotallyTorontoArt, you might find artwork inspired by Toronto’s skyline + winter reflections for the perfect keepsake.
5. Toronto Art Crawl Christmas POP UP – shopping for art & crafts
Held Sunday Dec 7, 2025 at The Great Hall, 1087 Queen Street West, this one-day pop-up brings together over 120 talented Toronto artists, artisans, fine art, jewellery, and home decor — an ideal place for holiday gifting (or treat-yourself). (torontoartcrawl.com)
Why it pairs with TotallyTorontoArt: While you’re homeward bound with your finds, stop by our site and browse curated art pieces (whether prints, originals, or wall-art) to complement your seasonal mood. Use this market outing as inspiration to decorate your space for the winter ahead.
🎨 Why TotallyTorontoArt is your holiday art partner
At TotallyTorontoArt we love capturing the vibe of Toronto’s season: the glow of lights, the architecture of grand venues, and the community of artists. As you explore these events, think of how a meaningful piece of wall-art can extend the memory.
-
We’ve hand-selected prints and originals that reflect Toronto’s festive landmarks, music halls, and winter panoramas.
-
Looking for a gift? Art is timeless. A print of Massey Hall’s stage, or a winter skyline photograph — perfect for someone who loves the city.
🎁 Bonus tip: Make a day of it
Pick one event in the afternoon (e.g., the art pop-up), enjoy dinner in the area (Queen W or the Distillery District), then end the evening at a concert (St. James or Massey Hall) or lights show (Nathan Phillips Square). These walks and moments make great photo ops — which in turn inspire the art you’ll bring home.
Wishing you a warm, art-filled, musical holiday season in Toronto!
From the TotallyTorontoArt team — may your walls tell stories of lights, sound, and inspiration.
Leave a comment