Toronto becomes a true winter wonderland each holiday season — with vibrant markets, magical light displays, festive performances, and family traditions happening all across the city. Whether you're planning holiday outings, exploring neighbourhood events, or considering Toronto as your next home, this 2025 Holiday Guide brings together the very best seasonal experiences.

Curated by Ana Bastas Realty, proudly serving Halton, the GTA, Hamilton & the Niagara Region, here is everything you need to celebrate the season in style.

🎄 1. Toronto’s Must-Visit Holiday Markets

✨ Distillery Winter Village (formerly the Toronto Christmas Market)

Address: 55 Mill St, Toronto
Dates: November 20, 2025 – January 5, 2026
Times: Mon–Thurs 12–9 PM | Fri–Sun 10 AM–10 PM
A magical European-style holiday destination with artisan vendors, live music, food cabins, fire pits, giant tree, and twinkling cobblestone streets.

🎁 Holiday Fair in Nathan Phillips Square

Address: 100 Queen St W
Dates: December 5–23, 2025
Times: Daily 12–10 PM
Skating, artisan vendors, carnival rides, food trucks, and Santa’s Snow Globe.

🛍️ Evergreen’s Winter Village at Evergreen Brick Works

Address: 550 Bayview Ave
Dates: December 6–21, 2025 (Weekends only)
Times: 10 AM–5 PM
Eco-friendly markets, local food, campfires, live music & sustainable holiday shopping.

🎭 2. Holiday Concerts, Theatre & Festive Shows

🎶 Toronto Symphony Orchestra – Holiday Pops

Address: Roy Thomson Hall, 60 Simcoe St
Dates: December 12–14, 2025
Times: Evening & matinee options
A spectacular holiday program with choirs, classic favourites & festive surprises.

✨ The National Ballet of Canada — The Nutcracker

Address: Four Seasons Centre, 145 Queen St W
Dates: December 5–28, 2025
Times: Matinee & evening showtimes
A beloved Toronto tradition for families and ballet lovers.

🎤 Carols at Casa Loma – Holiday Nights

Address: 1 Austin Terrace
Dates: December 1–30, 2025
Times: 5–10 PM
Carols, live entertainers, holiday lights & magical castle interiors.

❄️ 3. Outdoor Skating, Lights & Winter Magic

🧊 Nathan Phillips Square Skating Rink

Address: 100 Queen St W
Season: November 25, 2025 – March 2026
Hours: 10 AM–10 PM
Iconic holiday skating under the sparkling lights & Toronto sign.

🎄 Cavalcade of Lights

Address: Nathan Phillips Square
Date: November 22, 2025
Time: 6–10 PM
Official holiday kickoff featuring fireworks, tree lighting, DJ performances, skating & light installations.

🌲 High Park & Toronto Botanical Garden Winter Walks

Addresses:
• High Park – 1873 Bloor St W
• TBG – 777 Lawrence Ave E
Open: Daily, dawn–dusk
Scenic winter trails perfect for crisp December strolls.

✨ Toronto Zoo Holiday Lights – Terra Lumina

Address: 2000 Meadowvale Rd
Dates: December 1, 2025 – January 5, 2026
Times: 5:30–10:30 PM
Immersive light show, glowing pathways & interactive displays.

☕ 4. Cozy Cafés & Holiday Treats

Sorry Coffee Co. – Ossington
Holiday blends, spiced lattes & minimalist festive vibes.

Dineen Coffee – Yonge & Temperance
Iconic décor, warm drinks & holiday pastries.

Balzac’s Coffee – Distillery District
Perfect for a pre-market peppermint mocha.

Fika Café – Kensington Market
Scandi-inspired holiday atmosphere & seasonal desserts.

🍽️ 5. Festive Dining Experiences

🎄 Holiday Prix-Fixe Menus (Citywide)

Available: December 1–24, 2025
Top picks:

• Aloette
  
  
• Cluny Bistro
  
  
• BlueBlood Steakhouse (Casa Loma)
  
  
• Terroni Price St
  
  

🍷 Snow Globes & Winter Domes (Rooftop Dining)

Locations:
• The Rooftop at Broadview Hotel, 106 Broadview Ave
• The Porch Toronto, 250 Adelaide St W

Season: November 2025 – March 2026
Heated domes, city views & holiday menus.

🔥 Distillery Fire Pits (Evenings Only)

Warm drinks, s’mores & festive atmosphere.

🎅 6. Family-Friendly Holiday Fun

🎅 Toronto Santa Claus Parade

Route: Starting at Bloor & Parliament → University Ave → Front St
Date: November 16, 2025
Time: 12:30 PM
One of Canada’s biggest parades — floats, performers, musicians & Santa.

🎄 The Bentway Skate Trail

Address: 250 Fort York Blvd
Season: December 2025–February 2026
A 220-metre skate trail under the Gardiner — one of Toronto’s most unique winter experiences.

✨ Yonge-Dundas Square Winter Market

Address: 1 Dundas St E
Dates: December 19–24, 2025
Times: 12–9 PM
Holiday shopping, food vendors, live music & twinkling lights.

📚 Toronto Public Library Holiday Workshops

Locations: All Toronto branches
Dates: December 1–22, 2025
Festive crafts, kids’ storytimes, holiday DIY workshops & family activities.

🌟 7. Community, Culture & Holiday Spirit

Toronto’s holiday season is as diverse as the city itself — filled with multicultural festivals, charity drives, neighbourhood celebrations & inclusive winter events. Whether you’re enjoying cultural traditions or exploring Toronto as a future home, you’ll feel the warmth, creativity & community pride that defines this city.

🏡 Thinking of Buying, Selling, or Investing in Toronto?

From downtown condos to family homes in Etobicoke, Scarborough, Midtown, and North York, Toronto remains one of the strongest, most desirable markets in the country.

Our team is here to help you navigate it with clarity, confidence & the AB Advantage™.

✨ Wishing You a Magical Toronto Holiday Season

If you’d like a custom property list, neighbourhood guide, or Toronto market update, we’re here to support you.

Warmest wishes,
Ana Bastas & The Team
🏡 Ana Bastas Realty | Experience the AB Advantage™
Serving Halton, the GTA, Hamilton & the Niagara Region
📞 289.670.5888
🌐 www.anabastas.ca