Caledon Christmas Events & Things to Do 2025

Experience the magic of Christmas at Downey's Farm! Visit with Santa and his elves, enjoy festive wagon rides, and create your own reindeer food. Explore charming Christmas scenes, play mini-putt with a hockey stick twist, and delight in live entertainment. It's a perfect holiday outing for the whole family.

Experience the magic of the holiday season at Joy & Lights Weekend in Downtown Orangeville. This beloved event features a spectacular tree lighting ceremony and starlight shopping, creating a festive atmosphere for all. Discover unique gifts and enjoy the charming decorations that transform the downtown area into a winter wonderland.

Experience the magic of Christmas in The Park, a beloved holiday tradition in Orangeville. This free event transforms Kay Cee Gardens into a winter wonderland with millions of dazzling lights, enchanting mechanical displays, and captivating illuminated characters. For over 30 years, the Optimist Club of Orangeville has brought this festive...

Step into a world of holiday magic at WinterFest, Canada's biggest Christmas event! This immersive experience transforms the park with millions of shimmering lights, festive family activities, and new live entertainment. Indulge in delicious holiday-inspired comfort food and beverages while enjoying select park attractions. It's the perfect destination for cozy...

Discover Vaughan's dazzling Festival of Lights, a celebration of community spirit and holiday cheer. This program highlights homes and businesses that go above and beyond with their festive decorations. Join the launch event at Vaughan City Hall for entertainment and refreshments, and nominate outstanding displays that showcase creativity and energy-efficient...

Discover the enchanting Winter Lights display at Richmond Green Sports Centre and Park. This festive event transforms the city's largest park into a magical wonderland, perfect for a memorable holiday outing.

Step aboard vintage streetcars for a magical 'Christmas on the Rails' experience. Journey through a snow-dusted landscape accompanied by festive carols. Santa Claus makes a special appearance, sometimes even taking the controls of a streetcar. The entire museum grounds and historic streetcars are adorned with holiday decorations, creating a truly...

Step into a world of enchantment at Twinkle After Dark, an award-winning illuminated Christmas event. They showcase thousands of hand-carved pumpkins, artfully arranged to create dazzling holiday scenes. Wander through a magical wonderland where festive lights and creative pumpkin artistry combine for an unforgettable seasonal experience.

The annual Cavalcade of Lights transforms Nathan Phillips Square into a winter wonderland, kicking off the holiday season with a spectacular tree lighting ceremony and live performances. Visitors can enjoy nightly ice skating on the rink and marvel at festive light installations that create a magical atmosphere throughout the event.

Step into a winter wonderland at Christmas Town, where families can enjoy a magical guided wagon ride to visit Santa and Mrs. Claus in their woodland hideaway. Engage in festive activities like cookie decorating, craft making, and a holiday scavenger hunt. This enchanting experience also offers visits to the Elf...

Discover unique, handcrafted treasures at the annual Holiday Treasures Craft Market. This juried event showcases over 60 talented artisans offering a wide array of gifts, decor, and more. From intricate jewelry to festive home goods, find the perfect holiday presents. Enjoy a festive atmosphere with admission by donation.

Step into a magical winter wonderland at the fourth annual Merry Marketplace. Discover unique gifts from artisan vendors under thousands of twinkling lights. Enjoy festive food, warm beverages, and create lasting memories with family and friends. Don't miss the chance to meet Santa Claus every Saturday evening and participate in...

Experience the magic of the holidays at Santa at the Fairgrounds, returning for its fourth year. Families can visit Santa Morgan for photos, shop from a curated selection of local vendors, and enjoy the festive atmosphere. Warm up by the outdoor fire pits with a s'mores kit, creating cherished holiday...

Discover a unique, eco-minded holiday shopping experience at the Toronto Botanical Garden's annual Holiday EcoMarket. Browse over 80 local vendors showcasing planet-friendly and botanically-inspired products, perfect for finding distinctive gifts. Enjoy live music, delicious local eats from food trucks and artisanal vendors, and cozy up by the bonfire with complimentary...

Discover a unique, eco-minded holiday shopping experience at the Toronto Botanical Garden Holiday EcoMarket. Browse over 80 local vendors offering planet-friendly and botanically-inspired gifts, perfect for conscious consumers. Enjoy live music, festive food options, and family-friendly activities, including marshmallow roasting by the bonfire. It's a relaxed and nature-inspired way to...

Discover Canada's premier destination for handmade treasures at the One Of A Kind Winter Show. Celebrating 50 years, this event connects you with over 100 passionate Canadian artisans. Find unique gifts, explore diverse crafts from jewelry to home decor, and experience the spirit of small business. It's the perfect place...

Experience the charm of downtown Fergus during their Late Night Sip & Shop events. Explore local shops open late, enjoy festive caroling, and take a magical horse-drawn carriage ride. Santa Claus will be on hand for photos, and delicious food trucks will be available, creating a perfect old-fashioned Christmas atmosphere.

Experience a magical Nordic-inspired winter celebration at Holiday at The Well. This festive event transforms the space into a winter wonderland, featuring a vibrant Vendor Village with unique holiday shopping opportunities from eight small businesses. Enjoy curated programs, seasonal activities, and the enchanting Aurora Borealis light display.

Experience the magic of the season with Winterlude XII, the Milton Philharmonic Orchestra's annual holiday concert. This festive performance promises a delightful evening filled with seasonal favorites, opportunities for audience sing-alongs, and enchanting performances by special guest dancers presenting selections from the children's opera Hansel and Gretel. It's a perfect...

Experience the enchantment of The Nutcracker: A Canadian Tradition, a beloved holiday ballet by Ballet Jörgen. This captivating performance, set to Tchaikovsky's iconic score and choreographed by Bengt Jörgen, brings a unique Canadian flair to the classic tale. Audiences will be transported through magical dreamscapes featuring stunning backdrops inspired by...

Get into the holiday spirit with the Toronto Symphony Orchestra's TSO Holiday Pops concert. Led by guest conductor Sarah Hicks and featuring the captivating vocals of Mikaela Bennett, this festive spectacular promises an unforgettable experience. Immerse yourself in sparkling melodies, rousing choruses, and a heartwarming carol singalong, perfect for creating...

Campbell's Cross Farm transforms into a winter wonderland for their Marshmallow World Holiday Event. Visitors can explore a Christmas Tree Lot, enjoy festive tractor wagon rides, and meet Santa. Cozy up by fire pits in the maple forest for a truly magical holiday experience.

Experience the enchantment of the Brampton Santa Claus Parade, a beloved nighttime tradition. Witness a spectacular procession of dazzling floats, festive performances, and a grand fleet of helium balloons. This iconic event culminates with the magical arrival of Santa Claus, bringing holiday cheer to the streets of Brampton.

Get ready for a dazzling evening as the Mississauga Santa Claus Parade moves downtown for the 'Shine Bright, Sauga!' celebration. This festive event combines the beloved parade with the City's annual Light Up the Square, featuring a 35 ft. Christmas tree lighting, live entertainment, and family-friendly activities. Participants are encouraged...

Kick off the winter season in downtown Mississauga with a spectacular celebration! The festivities begin with live entertainment, festive photo opportunities, and ice skating at Celebration Square. The excitement culminates with the Santa Claus parade, featuring Santa lighting the Christmas tree, followed by trackless train rides and busker performances.

Get ready for a whimsical holiday celebration at the Milton Santa Claus Parade! This year's 'A Very Cartoon-y Christmas' theme transforms Main Street into a vibrant wonderland. Witness a spectacular parade featuring colorful floats and community participants. Don't miss the chance to contribute to the 'Stuff a Bus' food drive,...

Discover a vibrant calendar of community events and festivals hosted by the City of Richmond Hill. From lively Canada Day celebrations and popular Ribfests to seasonal workshops and the Merry Marketplace, there are engaging experiences for everyone. Explore extensive parks and recreational facilities, or get involved by hosting your own...

Experience a charming Olde Tyme Christmas at the Varley Art Gallery. This festive event invites visitors of all ages to craft their own mini Christmas tree ornaments, perfect for personalizing holiday decorations or giving as thoughtful gifts. Layer, decorate, and add sparkly details to create a unique keepsake.

Experience the magic of the holiday season at the Fergus Santa Claus Parade. This beloved community event features a vibrant procession of creative floats from local organizations and clubs, culminating in the much-anticipated arrival of Santa Claus himself. It's a joyous occasion that officially kicks off the festive spirit in...

The Original Santa Claus Parade is a beloved Toronto tradition that has kicked off the Christmas season for over 120 years. This iconic event brings hundreds of thousands to the streets and millions more to watch at home, celebrating hope, family, and love with spectacular floats, festive music, and the...

Join the vibrant Guelph Santa Claus Parade, a highlight of the 'Spirit of the Season' festival in historic Downtown Guelph. This beloved community event brings together residents for a spectacular celebration of the winter season, featuring dazzling lights, festive decorations, and the joyous arrival of Santa Claus.