Toronto is once again coming to life with festive energy! Today we’re sharing a handful of the seasonal community events that are lighting up the city. This time of year is especially exciting for Workhaus and our members, because we’re right in the middle of the action. This year, we’re highlighting events that are close to our locations, with something for everyone across the city: from downtown to the west end, all the way to North York. You can look forward to a stacked lineup of markets, pop-ups, performances, and neighbourhood traditions. With all that and more on the horizon, this season is shaping up to be one of the most festive yet. So, get ready to explore the best of what Toronto has to offer right outside our doors.
Toronto Holiday Events and Traditions
- St Lawrence Winter Market and Winter Market on Market Street
Thursdays through Sundays, now until December 23, enjoy live performances and entertainment, seasonal treats, and unique local vendors to shop with! Plus, enjoy even more treats, live entertainment, and 75+ vendors outside on Market Street. This holiday two-for-one is just a 10-minute walk from our Richmond and Adelaide St offices.
- Holiday at The Well
From November 12 until December 28, visit The Well to experience the season in full festive style. Check out themed events ranging from disco ice skating to immersive holiday installations, just a short walk from our Spadina Ave office.
- Holiday Event Series by Fort-York BIA
From December 6 to 18, experience a festive event series that includes a neighbourhood crawl. Prepare for a 19+ Gingerbread House night, a festive holiday drag brunch, and more, all conveniently close to our offices on Spadina Ave and King St West.
- Lunar New Year
On February 25 & 26, 2026, celebrate the Lunar New Year in Toronto’s Chinatown. Enjoy performers, vendors, Dragon Dance and more, all happening nearby our Dundas West and Spadina Ave offices.
- Holiday Hills
From November 14 to December 28, Tuesdays through Sundays, enjoy seasonal food and drinks, immersive displays, and more at Toronto’s only shipping container market turned holiday wonderland, all easily reachable from our Dundas St and Spadina Ave offices.
- Free Skate Rink in Nathan Phillips Square
All season long enjoy free ice skating at Nathan Phillips Square, complete with festive lighting and a lively downtown atmosphere. Perfect for a quick visit from our Dundas St or Spadina Ave offices.
- Winterfest Toronto
From November 28 to December 21, visit Toronto’s Harbourfront and get cozy by the fire, marvel at the 33-ft holiday tree, and enjoy festive lights and attractions, just steps from our Dundas West and Financial District offices.
- Miracle on Harbourfront
From November 20 to December 28 at Boxcar Social on Queens Quay West, enjoy a holiday pop-up bar and family-friendly experience. This event, located near our Financial District offices, and includes breakfast with Santa!
- New Years Eve Comedy Extravaganza at Massey Hall
On December 31, spend New Year’s Eve at Massey Hall laughing alongside a star-studded cast, featuring some of Canada’s most beloved comedians. The fun happens just a short distance from our Dundas West and Financial District offices.
- Winter Glow at Sankofa Square
From December 11 to 21. enjoy ferris wheel and carousel rides, a holiday artisan market, and brand activations (including giveaways and samples) in Sankofa Square. Catch it all just down the block from our Dundas West office.
- Cavalcade of Lights
Celebrate the season at Nathan Phillips Square, from now until January 7, 2026. Events and installations will include interactive artwork, ice skating (with free skate rentals), seasonal lighting displays, and a daily Menorah lighting over the week of December 14th. This beautiful installation is just a short walk from our Dundas West and Financial District offices.
- CF Winterville
All season long visit the CF Eaton Centre to enjoy festive performances, hourly light and snow shows at the iconic 114-foot tall tree, and even get a holiday portrait taken. All of this is just minutes away from our Dundas West and Financial District offices.
- Holiday lights tour of Casa Loma
December 5th to January 4th, see Toronto’s iconic castle all decked out in lights, and decorations. Plus, enjoy live performances around the castle grounds! Just hop on the subway right next to our Dundas West office, and this magical experience is only 15 minutes away!
- Festive Lights of Bloor-Yorkville
Now through the end of December, enjoy beautiful and elaborate festive lighting displays in this holiday shopping hotspot. The displays are conveniently situated along the subway line, making them easy to reach from any of our downtown offices.
- JRCC Menorah Lighting
On December 15th, celebrate the Festival of Lights at Mel Lastman Square with a Menorah lighting and live Chanukah concert, all just a short trip from our Sheppard Ave office.
- Evergreen Winter Market
On Sundays from November 30 to December 21, visit the Evergreen Winter Market to enjoy vintage and artisan vendors, delicious food trucks, a cozy winter garden with fire pits, skating, live performances, and more. This festive weekend tradition can be easily accessed via TTC.
- Holiday Windows (formerly at Hudson’s Bay)
From December 14 through the new year, catch the return of Toronto’s beloved holiday window displays at the former Hudson’s Bay and Saks Fifth Avenue building. Now revived by Cadillac Fairview, these festive installations continue a cherished city tradition, with new themed displays lining Yonge, Bay, and Richmond Streets. This nostalgic holiday stop is close to our Financial District locations and just around the corner from our Richmond St office.
Celebrate the Season with Workhaus
We hope you found your next favourite winter activity somewhere on our list. If there’s a hidden gem we missed, let us know in the comments on instagram.
Meanwhile, we’ve spent the past week celebrating the season with our community of members at each of our Workhaus locations. These end of year socials were all about spending time together and celebrating the achievements of the past year, as we gathered over food, drinks, and crafts to chat, network, and chill. Now we’d like to thank our members for making these events so special!
