Milton Christmas Events & Things to Do 2025

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 the magic of the season at Woodbine Mohawk Park's 3rd annual Winter Wonderland & Market. This festive event invites visitors to shop for unique holiday gifts from over 40 local vendors, enjoy family-friendly activities like a magic show and face painting, and meet Santa Claus. Don't miss the enchanting...

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 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 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 a vibrant holiday shopping experience at the Cambridge Holiday Market, a beloved event that has grown significantly since its inception. This year, the market spans four floors of City Hall and the Cambridge Centre for the Arts, showcasing products from over 200 local artisans, crafters, and makers. Visitors can...

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 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...

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.

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...

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...

Wander through Mountsberg Conservation Area's enchanting Winterlit display, an award-winning celebration of nature and light. Explore two illuminated trails featuring sustainably sourced art installations, cozy fireside lounges, and interactive elements like a book nook and animal den. Special Enchanted Evenings offer a magical experience with live performances and a licensed...

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...

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.

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 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...

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...

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...

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 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...

Immerse yourself in the holiday spirit with The Nutcracker Holiday Spectacular. This enchanting performance features a traditional Act II of The Nutcracker ballet, alongside a collection of cherished holiday classics. Showcasing the exceptional talent of local art groups and many youth performers, it's a vibrant celebration of community and festive...

Get into the holiday spirit with 'A Swingin' Christmas,' featuring the Toronto All-Star Big Band. This festive revue presents swinging renditions of seasonal favorites and timeless classics from the golden age of swing, reminiscent of a classic Christmas Special. It's a genuine time capsule designed to evoke cherished memories and...

Step into a world of holiday enchantment with Elvis’ Wonderful World of Christmas: Graceland Edition. This dazzling tribute to the King of Rock ‘n’ Roll, starring World Champion Elvis Tribute Artist Steve Michaels, brings the festive magic of Graceland to life with the warmth and spirit of Christmas. A night...

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.

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...

Step back in time for an immersive Nativity pageant at Walk to Bethlehem. This event recreates the journey from prophecy to the manger, bringing the story of Jesus' birth to life. Hosted by SGSA Coptic Orthodox Church, it offers a profound experience of a pivotal biblical moment.

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 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....

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 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...

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.

Experience the magic of the holiday season at Music and Lights in the Village! This festive event transforms Hespeler Village into a winter wonderland with dazzling lights and a special tree lighting ceremony. Enjoy live music from talented local performers, including school choirs and bands, and warm up with complimentary...

The CPKC Holiday Train makes a special stop in Cambridge, bringing a free concert and holiday cheer. This festive event features live performances from popular artists like JJ Wilde and Smash Mouth, all from the brightly decorated train. Attendees are encouraged to bring food or monetary donations for the Cambridge...

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...

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...