Our Favourite Holiday Spots in Toronto
Toronto just hits different at Christmas. The lights, the energy, the cozy neighbourhood moments — it’s one of our favourite times of the year. Whether you’re planning festive outings with the kids, a seasonal date night, or just looking for ways to enjoy the city, here are our go-to holiday spots across Toronto.
1. The Distillery Winter Village — A Family Staple
Between the oversized tree, mulled wine, local vendors, and that classic cobblestone charm, it feels like stepping into a Christmas movie.
Why we love it: Perfect mix of holiday magic, great for gift shopping, always a vibe.
2. Skating at Nathan Phillips Square — A Toronto Essential
Skating under the Toronto sign is practically a December rite of passage. Whether you glide or shuffle, it’s fun, festive, and kid-approved.
Why we love it: Iconic views, family-friendly, hot chocolate tastes better here for some reason.
3. Casa Loma’s Holiday Lights — Pure Fairytale Energy
If you want a magical evening, Casa Loma is it. The castle transforms with lights, festive installations, and soaring Christmas trees. It’s stunning every single year.
Why we love it: Dreamy ambience, amazing for families, feels special.
4. Yorkville Lights — Classy, Cozy, Perfect for a Night Out
Yorkville brings elegant holiday charm. Stroll the twinkling streets, window shop, and wrap up the night with dinner or a festive drink.
Why we love it: Romantic, stylish, ideal for a seasonal date night.
5. Evergreen Brick Works Winter Village — Rustic & Outdoorsy
A beautiful mix of nature, local vendors, and firepits. It’s the perfect spot for families or anyone who wants a quieter, outdoorsy holiday moment.
Why we love it: Relaxed vibe, great for kids and pups, very “Toronto winter.”
6. The Bentway — Skating Under the Gardiner
Urban, cool, and surprisingly festive. The Bentway turns into a unique skating trail, complete with lights and music.
Why we love it: Fun atmosphere, perfect for teens, feels fresh and modern.
7. High Park Trails — Peaceful Winter Strolls
On chilly December mornings, nothing beats a walk through High Park. Light snow, quiet paths, and a break from holiday chaos.
Why we love it: Family strolls, dog walks, and a great way to reset.
8. Kensington Market — Holiday Spirit With Personality
Colourful, creative, and full of energy, Kensington gives you a non-traditional holiday experience with incredible food and quirky charm.
Why we love it: Amazing food, vibrant atmosphere, great for wandering.
9. West End Holiday Shops & Cafés — Local Love
From Roncesvalles to Bloor West Village, the west end shines during the holidays. Local businesses go all-out with warm drinks, festive windows, and neighbourhood buzz.
Why we love it: Supporting local, cozy cafés, and a fun way to explore the community.
The holidays are about connection — not just with the people we love, but with the city we call home. Whether you’re enjoying festive outings, cozy nights in, or snowy morning walks, we hope this season brings warmth, joy, and lots of memorable moments.
From our family to yours, happy holidays and happy exploring!
