What to Expect This Christmas in Caledon!
Caledon christmas charm lights Bolton and the Forks of the Credit with holiday markets, craft fairs, and seasonal walks among scenic countryside. Visit local artisan stalls, enjoy cozy events in Caledon Village, and family-friendly festivals for rural holiday warmth.
Find the best Christmas events in Caledon this year!
Top Holiday Events In and Around Caledon
- Christmas at the Farm
- Christmas in The Park (Orangeville)
- Orangeville Winter Farmers' Market (Orangeville)
- Elliott Tree Farm Christmas Tree Experience (Hillsburgh)
- Boo on Broadway (Orangeville)
- Canada's Wonderland WinterFest (Vaughan)
- Holiday Fair in the Square (North York)
- Milton Santa Claus Parade (Milton)
- Twinkle After Dark (Milton)
- Holiday Bricktacular at LEGOLAND Discovery Centre Toronto (Vaughan)
🎃 Explore all 10+ featured events below!
Caledon Holiday Events
Caledon Christmas Markets and Shopping (3)
When
Saturday, November 29, 2025
Event Details
Event Description
Experience the enchantment of Christmas at the Farm, hosted by Downey's Farm Market. Santa and his elves are set to return, bringing holiday cheer to visitors of all ages. Explore the farm store for delicious baked goods and seasonal treats, and find the perfect Christmas tree to make your holidays bright.
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Event Details
Event Description
Experience the charm of the Orangeville Winter Farmers' Market, held indoors at Town Hall. Discover a delightful array of fresh local produce, artisanal meats, and unique baked goods. Browse handcrafted items from rotating vendors in a warm and welcoming atmosphere, perfect for starting your weekend.
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When
Saturday, November 15, 2025
Event Details
Event Description
Experience the magic of the holidays at Elliott Tree Farm's Christmas Tree Experience. Wander through a winter wonderland, choose from a vast selection of fresh-cut or cut-your-own Christmas trees, and enjoy festive amenities like the heated Horse Barn Canteen and the Maple Syrup Museum of Ontario. It's the perfect destination for creating cherished family traditions.
MoreCaledon Christmas Light Displays (1)
When
Sunday, December 1, 2024
Event Details
Event Description
Experience the enchantment of Christmas in The Park, a beloved annual tradition in Orangeville. Kay Cee Gardens is transformed into a dazzling spectacle with millions of lights, magical mechanical displays, and captivating illuminated characters. This free, month-long event draws thousands of visitors to enjoy the festive atmosphere, community displays, and the spirit of the holidays.
MoreCaledon Other Christmas Activities (1)
Event Details
Event Description
Celebrate the close of the outdoor market season with Boo on Broadway! This event transforms the downtown area into a Halloween wonderland with exciting trick-or-treating opportunities, spine-chilling haunted houses, and a dazzling display of jack-o'-lanterns. It's a perfect way for families to enjoy the festive spirit of the season.
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