Pickering Christmas Events & Things to Do 2025

Step into a festive wonderland at Pickering Museum Village for A Storybook Christmas. Follow Teddy's enchanting tale through interactive holiday elements, including crafts, games, and delightful treats. This immersive experience is perfect for all ages, culminating in a special visit from Santa Claus himself.

Experience the magic of the tenth annual Picks & Giggles Classic Holiday Market, returning to the Oshawa Centre. This beloved event brings together over 300 local Canadian businesses, offering a unique shopping experience with fresh vendors and surprises each weekend. Discover one-of-a-kind holiday gifts, indulge in seasonal treats, and enjoy...

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...

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...

Get ready for the enchanting Leslieville Christmas Pop-Up Market! This festive event brings together over 60 unique vendors offering everything from stylish clothing and artisanal jewelry to delicious foods and thoughtful gift sets. Kick off the holiday season with a special Friday night party featuring drink tastings, '90s music, and...

Discover the annual Holly Berry Fair at Rosedale United Church, a festive two-day event brimming with Christmas shopping and entertainment. Browse unique artisan vendors, explore a treasure-filled thrift market, and delight in delicious homemade treats. Children can visit Santa's interactive workshop, while everyone can enjoy the lively atmosphere and support...

Experience the magic of the season at the Riverside Holiday Market! This festive event welcomes everyone to enjoy a day filled with holiday cheer. Discover unique gifts and artisanal products from over 20 local vendors, perfect for your Christmas shopping. Capture memorable moments with a free meet and greet for...

Discover a festive holiday shopping experience at the Uxbridge Farmers' Market's Holiday Markets. Browse over 30 local artisans offering handcrafted gifts, art, and home decor. Indulge in delicious baked goods, artisanal foods, and fresh produce. Enjoy live music during select markets and find unique treasures for everyone on your list.

Step into a magical winter wonderland at The Distillery Winter Village. This beloved Toronto event transforms the historic Distillery District into a festive hub, featuring over 100 artisan vendors offering unique gifts, crafts, and seasonal delights. Wander through charming cobblestone streets adorned with twinkling lights, explore a diverse range of...

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.

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...

Immerse yourself in the festive spirit at Pickering's annual 'Winter Nights, City Lights' celebration. This magical event transforms Esplanade Park and the Chestnut Hill Developments Recreation Complex into a winter wonderland. Witness the breathtaking tree lighting ceremony, explore a charming holiday market brimming with unique gifts and artisanal crafts, and...

Experience the magic of the holiday season with Journey Into Enchantment, a captivating drive-thru Christmas light show. This event features over 2 million lights along a 2-kilometer route, showcasing favorite holiday characters, a dazzling drive-thru tunnel, and musical light displays synchronized to festive melodies. It's a family-friendly spectacle designed to...

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.

Get ready to ignite your holiday spirit at the Rosedale Cavalcade of Lights! This annual celebration promises a sleighful of festive fun for everyone. Marvel at the dazzling tree lighting ceremony, enjoy a magical ride on the Cavalcade Express Train, and sing along to carols. Meet beloved characters, savor the...

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.

Experience the enchantment of Moonlight Magic, Bowmanville's annual Christmas tree-lighting ceremony. This festive evening features a special visit from Santa Claus, delightful children's entertainment, and heartwarming carol singing. Enjoy complimentary horse-drawn wagon rides, explore downtown businesses with extended shopping hours, and savor treats from local vendors.

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...

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...

Immerse yourself in the enchanting atmosphere of Candlelight Concerts in Oshawa. These unique events transform familiar venues into intimate, candlelit spaces, offering a magical backdrop for incredible musical performances. Experience a diverse range of music, from classical masterpieces to contemporary hits, all performed by talented musicians in an unforgettable setting.

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...

Experience the timeless magic of The Nutcracker, celebrating 30 years of enchantment. This beloved holiday tradition, choreographed by James Kudelka, transports audiences to a 19th-century Russian Christmas Eve. Follow siblings Marie and Misha as they embark on a dreamlike adventure filled with magical creatures, delightful treats, and the glittering Land...

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...

Get ready for a festive evening with the Professors of Funk Friends & Family Christmas Special. This special holiday concert promises a lively performance filled with funk and Christmas spirit, perfect for a family outing. Experience the joy of the season with great music in a welcoming atmosphere.

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...

Get ready for the much-anticipated Santa Claus Parade in Pickering! This year's theme, 'No Place Like Home for the Holidays,' invites everyone to showcase their Pickering Pride. Experience a dazzling procession of floats from local businesses and community groups, accompanied by lively marching bands, all culminating in the magical appearance...

Get ready for the City of Pickering's Santa Claus Parade on November 22, 2025! This beloved annual event, themed 'No Place Like Home for the Holidays,' promises a spectacular display of extravagant floats from local businesses and community groups, accompanied by lively marching bands. It's the perfect way to kick...

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.

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...

Embark on a magical holiday journey aboard the Santa Train, a cherished tradition for families. This festive excursion offers a delightful train ride, a special chance to meet Santa Claus for photos, and the enjoyment of seasonal treats. Advance booking is highly recommended to secure your spot on this popular...

Step into a piece of history at St. Lawrence Hall, a venue built in 1850 and restored to its original grandeur. This breathtaking space, featuring three distinct rooms, has been the backdrop for countless memorable occasions, including weddings and holiday parties. Its historic charm and character provide a warm and...

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...