Oakville Christmas Events & Things to Do 2025

Join the festive spirit at the 31st Annual Kerr Village Christmas Tree Lighting & Holiday Market. This beloved event transforms Kerr Village into a winter wonderland, perfect for families and individuals looking to embrace the holiday season. Discover unique gifts, savor seasonal treats, and experience the joy of community.

Experience the magic of the Oakville Christmas Market, a delightful event featuring a curated selection of local artisans. Discover unique, handmade gifts and festive decorations, perfect for your holiday shopping. Indulge in seasonal treats and warm beverages while soaking in the cheerful holiday atmosphere. It's the ideal destination to find...

Join the 31st Annual Kerr Village Christmas Tree Lighting & Holiday Market for a festive celebration. Explore a vibrant holiday market filled with unique gifts and artisanal products. Enjoy live music and entertainment, and don't miss the special visit from Santa Claus, where children can drop off their letters. The...

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...

Experience the magic of the Hess Winter Village & Market, a festive celebration in Hamilton's historic district. They offer a delightful array of local vendors, seasonal activities, and opportunities to support a great cause. Enjoy unique crafts, festive treats, and community spirit.

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 magic of Winter Wander in Westdale Village! This festive event transforms the area into a winter wonderland with live music, holiday shopping, and family fun. Explore the charming streets adorned with festive lights and decorations, and discover unique gifts from local artisans. Don't miss special performances, including The...

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.

Step into a magical Winter Wonderland at the Grimsby Museum for the 26th annual Fantasy of Trees. This beloved event showcases dozens of beautifully decorated trees and wreaths, offering a festive atmosphere for the whole family. Participate in raffles or an online auction for a chance to win these holiday...

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 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...

Celebrate 30 years of enchantment at the Burlington Festival of Lights! From late November to early January, the waterfront becomes a breathtaking winter wonderland, illuminated by over 60 dazzling displays. This beloved tradition invites everyone to stroll or drive through the sparkling lights, creating unforgettable holiday memories.

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.

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...

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 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...

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.

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...

Immerse yourself in the holiday spirit with The Nutcracker, presented by the Oakville School of Classical Ballet. This enchanting production brings Tchaikovsky's beloved score to life, following Clara's whimsical journey through a magical winter wonderland. It's a festive and captivating experience for the whole family.

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...

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...

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...

Step back in time with Theatre Ancaster's special Christmas benefit performance of Charles Dickens' 'A Christmas Carol.' This unique production brings the beloved holiday classic to life through the captivating style of a 1940s Radio Theatre broadcast, complete with vintage microphones, live sound effects, and a talented ensemble of voice...

Step into a sparkling winter wonderland with the Theatre Ancaster Chorus for 'Let It Snow.' This festive concert is packed with cozy holiday vibes and frosty fun, promising a feel-good experience for all.

Step into a festive wonderland at Miracle, a Christmas-themed pop-up cocktail bar that has become a beloved holiday tradition since 2018. They transform their space with kitschy decor and serve delicious holiday cocktails, creating an atmosphere of pure nostalgia. A portion of every drink sold and door fee benefits Nellie's...

Discover Downtown Oakville's outdoor shopping experience, a festive destination where history and modern charm meet. Explore historical buildings and trendy boutique shops while savoring international cuisine. Admire the charming store displays and the spectacular Winter Wonderland of Lights, promising a guaranteed festive season with their hometown holiday events.

Join the beloved Oakville Santa Claus Parade, a cherished annual tradition celebrating its 76th year! This year's theme, 'Snow Much Fun!', captures the excitement of winter activities. Spectators can enjoy a vibrant procession of floats and participants, while community groups, schools, and businesses are invited to join the parade itself....

Capture the magic of the holiday season with professional family photos alongside Santa Claus at the historic Bradley Museum. This special event offers a wonderful opportunity to create lasting memories. Additionally, a dedicated 'Paws 'N Mr. Claus' session allows beloved pets to join in the festive fun. Proceeds from these...

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 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...

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,...

Get ready for the magical return of the Burlington Santa Claus Parade! This beloved annual event brings the community together to celebrate the start of the holiday season. Watch as festive floats and participants make their way through the streets, culminating in the grand arrival of Santa Claus himself. It's...

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.

The 68th annual Grimsby Santa Claus Parade is a cherished community tradition, marking a festive kickoff to the holiday season. This beloved evening event, which began in 2000, features approximately 90 diverse entries, including creative community floats, engaging walking groups, and lively marching bands. It's a perfect opportunity to gather...

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.