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Holiday Events in Toronto to Beat the Winter Blues

November 4 2025 | City

Holiday Events in Toronto to Beat the Winter Blues

I’ve learned that the only way to get through the changing weather is to embrace the shows and cookies that come along with the colder weather.

SO, here are my top picks for Toronto’s holiday season outings.

🎶 TSO Holiday Pops – Roy Thomson Hall

A joyful mix of Christmas classics, sing-alongs, and orchestral sparkle led by Sarah Hicks. Perfect for all ages (6+). This will make you feel a little refined while you worry one of your children is going to scream “this is boring” too loudly.. Make them bored; it’s good for them.

  • 📍 Roy Thomson Hall
  • 🍽️ Nearby: One Restaurant (1 University Ave) for a meal before or after.

🎟️ Buy Tickets Here


🎭 Robin Hood: A Very Merry Family Musical – Elgin & Winter Garden Theatre

A hilarious, interactive panto twist on Robin Hood — full of jokes, songs, and Toronto-style cheer. Great for kids 4+. This is something they’ll really love. I’m bringing my kids on December 14th and can’t wait!

  • 📍 189 Yonge St
  • 🍽️ Nearby: Richmond Station (1 Richmond St W). Get the Burger!

🎟️ Buy Tickets Here


🩰 The Nutcracker – National Ballet of Canada

A holiday classic with Tchaikovsky’s score and magical sets by the National Ballet. Ideal for ages 7 and up. A perfect afternoon for all, and my fave of the christmas events each year.

  • 📍 Four Seasons Centre, 145 Queen St W
  • 🍽️ Nearby: Marvelous Fred for croissants and coffee ahead of time.

🎟️ Buy Tickets Here


🐸 Disney’s The Muppet Christmas Carol in Concert – Meridian Hall

The beloved film with a live orchestra — Kermit, Miss Piggy, and friends bring the story (and music) to life. Ages 5+. A fun one for the cartoon goers

  • 📍 1 Front St E
  • 🍽️ Nearby: The Old spaghetti Factory – don’t mess with a good thing.

🎟️ Buy Tickets Here


See you when the curtain lifts.

Is buying or selling a home in your holiday plans? I’d be happy to help. Get in touch today by filling out the form on this page, texting me at 416-728-5401, or emailing me at ddemerino@royallepage.ca.