Annex Christmas 2025

What to Expect This Christmas in Annex!

Welcome to your ultimate guide for the holidays in Annex! Explore the best festive events and attractions. Whether you're rediscovering Annex or falling in love with it for the first time, this guide maximizes your holiday cheer. Popular events this season include the Distillery Winter Village, where charming markets and sparkling lights create a cozy atmosphere. The Winter Festival of Lights showcases stunning light displays that illuminate the city’s parks and waterfront, drawing visitors of all ages. And the Cavalcade of Lights is something you definitely don't want to miss, featuring dazzling fireworks and live entertainment to kick off the holiday season. See more details on these and other fun events and activities below!

Find the best Christmas events in Annex this year!

Annex Christmas Events

Annex Christmas Markets and Shopping (1)

Bloor-Yorkville Holiday Magic in Toronto

Details

📍 Toronto, ON, CA

(0.7 mi from Annex)

Bloor-Yorkville Holiday Magic

Upscale neighborhood with luxury shopping and dining.

Event Details

📷 Photo Friendly: 📷📷📷📷📷

💰 Budget: $$$

🎄 Family Friendly: 🎄🎄🎄🎄🎄

⚡ Energy: Moderate

Event Description

Experience the enchanting Bloor-Yorkville Holiday Magic, a celebration of luxury, culture, and festive cheer. Wander through charming streets adorned with seasonal decorations, explore high-end boutiques offering unique gifts, and indulge in world-class dining. This vibrant neighborhood transforms into a winter wonderland, perfect for a sophisticated holiday outing.

More

holiday_marketholiday_shoppingartisanal_productsfestive_foodluxury_shopping

⭐ Best For: Couples, shoppers, foodies

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Near Annex

Bay Street Corridor Christmas Events

Cavalcade of Lights in Toronto

Toronto

Details

Cavalcade of Lights

Iconic tree lighting and nightly ice skating

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 1.6 miles from Annex

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Campbell House Museum Events in Toronto

Toronto

Details

Campbell House Museum Events

Historic Georgian architecture in downtown Toronto

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 1.6 miles from Annex

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See all 4 events in Bay Street Corridor →

Rosedalemoore Park Christmas Events

Holly Berry Fair in Toronto

Toronto

Details

Holly Berry Fair

Annual Holly Berry Fair with artisan vendors and thrift market.

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 1.8 miles from Annex

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Dovercourtwallace Emersonjunction Christmas Events

Miracle Pop-Up Cocktail Bar in Toronto

Toronto

Details

Miracle Pop-Up Cocktail Bar

Christmas-themed pop-up cocktail bar with kitschy decor

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 1.2 miles from Annex

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Niagara Christmas Events

Kensington Market Winter Solstice Festival in Toronto

Toronto

Details

Kensington Market Winter Solstice Festival

Community parade celebrating the winter solstice.

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 1.1 miles from Annex

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Holiday at The Well in Toronto

Toronto

Details

Holiday at The Well

Nordic-inspired winter celebration with Vendor Village.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 2.1 miles from Annex

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See all 4 events in Niagara →

Moss Park Christmas Events

The Original Santa Claus Parade in Toronto

Toronto

Details

The Original Santa Claus Parade

Over 120 years of tradition

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 2.0 miles from Annex

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Distillery District Breakfast Tour in Toronto

Toronto

Details

Distillery District Breakfast Tour

Guided breakfast tour in Toronto's historic Distillery District.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 2.6 miles from Annex

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See all 4 events in Moss Park →

Toronto Christmas Events

Toronto City Fall Market in Toronto

Toronto

Details

Toronto City Fall Market

Local vendors offering handcrafted goods.

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 2.5 miles from Annex

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Waterfront Communitiesthe Island Christmas Events

Holiday Dining at the CN Tower in Toronto

Toronto

Details

Holiday Dining at the CN Tower

Dining atop the CN Tower with revolving city views.

📷📷📷📷📷 💰 $$$$ 🎄🎄🎄🎄🎄

📏 2.2 miles from Annex

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CN Tower Lighting Schedule in Toronto

Toronto

Details

CN Tower Lighting Schedule

Iconic tower illuminated nightly for causes and events

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 2.2 miles from Annex

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South Parkdale Christmas Events

Medieval Times Dinner & Tournament Toronto in Toronto

Toronto

Details

Medieval Times Dinner & Tournament Toronto

Knights battle with swords and jousting during a four-course feast.

📷📷📷📷📷 💰 $$$ 🎄🎄🎄🎄🎄

📏 2.9 miles from Annex

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South Riverdale Christmas Events

Riverside Holiday Market in Toronto

Toronto

Details

Riverside Holiday Market

Community holiday market with Santa, crafts, and winter window showcase.

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 2.8 miles from Annex

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The Toronto Flea Holiday Market in Toronto

Toronto

Details

The Toronto Flea Holiday Market

Curated market with vintage and handcrafted goods

📷📷📷📷📷 💰 $ 🎄🎄🎄🎄🎄

📏 4.1 miles from Annex

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Banburydon Mills Christmas Events

Toronto Botanical Garden Holiday Market in Toronto

Toronto

Details

Toronto Botanical Garden Holiday Market

Eco-minded, nature-inspired holiday market with over 60 local vendors.

📷📷📷📷📷 💰 FREE 🎄🎄🎄🎄🎄

📏 4.9 miles from Annex

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Winter Blooms | Circus at the Garden in Toronto

Toronto

Details

Winter Blooms | Circus at the Garden

Intimate, high-flying circus show with aerial silks and acrobatics.

📷📷📷📷📷 💰 $$ 🎄🎄🎄🎄🎄

📏 4.9 miles from Annex

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Our Process

With 20 years of experience, we use AI technology to build the most comprehensive list of christmas events events.

Our goal is complete coverage—from major festivals to small community celebrations, ensuring you never miss anything happening in your area.

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Last updated: 10/9/2025