Cozy Up, Toronto and Surrounding Areas! Your Perfect Winter Weekend is Waiting

The magic of the season has officially descended upon Toronto and surrounding areas, transforming the city and its charming neighbours into a festive winter wonderland. From lighting ceremonies and massive artisan shows to the return of iconic outdoor skating, the region is bursting with holiday cheer this weekend.

Whether you're looking for family fun, a romantic date night, or a one-of-a-kind shopping experience, save this post and start planning your perfect few days!

✨ Kick Off the Season with Festive Lights & Community Cheer

1. Markham Annual Festival of Lights

The heart of Markham lights up for its cherished annual tradition!

Get ready to feel the holiday spirit in full force as the community gathers to illuminate Main Street. This event is the quintessential cozy way to welcome winter, featuring live entertainment, family activities, and the much-anticipated Christmas tree lighting.

• When: Friday November 28, 2025 | 5:30 p.m. – 9 p.m.

• Where: Main Street, Markham

2. Winterfest Toronto

Experience the city's newest and largest magical winter wonderland right on the waterfront!

Winterfest Toronto returns to the Harbourfront Centre, promising an unforgettable experience for all ages. Wander through twinkling lights, explore festive food stalls, sip on mulled wine, and brave the 200’x60′ Giant Wooden Maze Experience! It’s the perfect place to embrace the cold with a warm beverage in hand.

• Key Highlights: Artisan Market (Indoor/Outdoor), Marshmallow Fire Pits, Winter Train Rides, Outdoor Ice Skating, and a spectacular 33 Foot Tall Walk-in Tree.

• When: November 28 to December 21, 2025 (Every Friday 6pm-11pm, Saturday 4pm-11pm, Sunday 4pm-8pm)

• Where: Harbourfront Centre, 235 Queens Quay W, Toronto

⛸️ Lace-Up and Glide into Winter

3. Nathan Phillips Square Ice Skating

The most iconic outdoor skating rink in the city is back!

Glide beneath the Toronto sign and City Hall arches at one of the city's most beloved winter staples. Whether you're a seasoned skater or just starting out, taking a spin on the Nathan Phillips Square Ice Skating rink is a must-do to truly soak in the downtown holiday atmosphere.

• When: November 29th, 2025 – March 16th, 2026 | 10am – 9:45pm Everyday

• Where: Nathan Phillips Square, Queen Street West, Toronto

🎁 Find the Perfect Gift (and a Treasure for Yourself)

4. One Of a Kind Christmas Show | 50th Anniversary

Celebrate five decades of Canadian creativity and craftsmanship!

For 50 years, the One Of a Kind Christmas Show has been Canada's favourite holiday shopping tradition. Head to the Enercare Centre to browse unique gifts from over 700+ artisans and makers. Discover a brand-new Vintage Section, a European-style Christmas Market, and an expanded Flavours section. It's the ultimate destination to shop local and support Canadian small businesses this holiday season.

• When: Thursday November 27, 2025 to Sunday December 7, 2025

• Hours: Mon–Wed & Sat (10am–8pm), Thu & Fri (10am–9pm), Sun (10am–5pm). Late Night Shopping on Thursday, December 4 until 11pm.

• Where: Enercare Centre, 100 Princes’ Blvd, Toronto

Is Your Home Wish List as Unique as These Events?

From a charming Markham street to a downtown condo with a view of the skating rink, the perfect winter weekend is often defined by where you live. The unique character and community spirit of Toronto and surrounding areas make it a truly special place to call home.

If you love the convenience of city living paired with the charm of community events, now might be the perfect time to explore properties that put you right in the middle of the action!

Ready to find a home in a community that feels this magical year-round?

Connect with Khoa Le, a local real estate expert who can help you find your next festive, family-friendly, or fantastic home in Toronto and surrounding areas!

👩🏻‍💼 Khoa Le, Broker
📱 647-271-5461
📧 khoa@realimpactgroup.com
🏡 @realimpactgroup | @realbrokerage