A festive day of markets, lights, warm drinks, and winter vibes. It’s late November, the Toronto Holiday Magic: Markets, Pop-Ups & Cozy Winter Moments and I hopped on a bus for the 5-hour ride from Ottawa to Toronto — all for one reason: to rediscover the magic of Christmas in the city.
Why the bus? Easy. It’s about $40, cheaper than one night of parking downtown, cheaper than gas, and honestly… stress-free. Why not?
Where I Stayed: Chelsea Hotel, Toronto
I checked into the Chelsea Hotel on Gerrard Street, right in the centre of everything.
- Steps from subway and bus lines
- A 20-minute walk to Union Station
- Restaurants and cafés all around
- And a Santa in the lobby — greeting kids, collecting wish lists, and celebrating his 25th season at the hotel (Fridays to Sundays until December 21st)
The Chelsea is one of those stays that makes downtown Toronto surprisingly easy to explore.
🎄 Toronto Christmas Market – Distillery District
My first stop: the iconic Toronto Christmas Market in the Distillery District.
I slipped in right before 4 p.m. and saved the entrance fee (around $17).
It was still busy — but in the best way. The kind that reminds you the holidays have officially arrived.
Expect:
• Food stalls everywhere
• Adult holiday drinks
• Endless hot chocolate (seriously, it’s everywhere)
• Lights, decor, musicians, and that festive rush you only feel in the Distillery
It’s one of those places that instantly puts you in a holiday mood.
🎅 Pop-Up Holiday Bar: Jingle Java (Little Sister Portland)
Next stop: Jingle Java — Toronto Holiday Magic as a holiday pop-up bar inspired by Little Sister Portland.
Located right on Queen Street, Jingle Java is fun, cozy, festive, and buzzing with holiday energy — the perfect second drink stop to warm up before dinner. The team was fantastic, the atmosphere playful, and the whole concept just works. It’s the kind of spot you want to bring friends to, because the vibes are that good.
We arrived just in time for happy hour and ordered crispy chicken bites and oyster shrooms to start, paired with one of their holiday cocktails. And the star of the night? Their melt-in-your-mouth pork belly — absolutely unforgettable.
CP Rail Christmas Train
The CP Holiday Train rolled into Toronto at 8:30 p.m., and the excitement built long before it arrived — social media was already buzzing with clips from the previous stop. Hopefully, you brought a non-perishable item to support the local food bank, because this event brings the community together in the best way.
The crowd was huge, the atmosphere electric, and Toronto Mayor Olivia Chow kicked things off before the performers took the stage. The artists delivered — energetic, engaging, and exactly the kind of feel-good entertainment that makes the holidays in Toronto unforgettable.
❤️ Why I Love Toronto During the Holidays
Because Toronto changes.
Lights everywhere.
Open markets.
The smell of cinnamon and comfort food.
People bundled up and smiling.
That unmistakable city buzz.
It’s festive, warm, nostalgic, and a little bit cinematic — like stepping into a Canadian Christmas movie.
Frequently Asked Questions
Absolutely. Go before 4 p.m. for free entry and fewer crowds.
Not if you stay downtown. Toronto transit + walking works perfectly.
The Chelsea Hotel is centrally located, affordable, and perfect for a quick holiday getaway.
Late November through mid-December — lights and markets are in full swing without the peak holiday crowds.
✍️ About the Author
Written and photographed by Roland Bast, Canadian travel photographer and visual storyteller based in Ottawa–Gatineau. Roland collaborates with tourism boards, hotels, and travel brands across Canada to capture authentic stories through photography.
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