Explore the charm of Pickering this holiday season with our comprehensive guide. For Pickering natives and tourists alike, this guide is your key to the city's holiday magic.
Kick-start your festive season with the time-honored Santa Claus Parade, a spectacle of floats and holiday cheer that winds through the heart of Pickering. Immerse yourself in the lively atmosphere and unique finds at the Christmas Market, known for its local crafts and delicious treats. And the Cavalcade of Lights is something you definitely don't want to miss, lighting up the night with stunning displays. See more details on these and other fun events and activities below!
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Top Holiday Events In and Around Pickering
- Santa Claus Parade
- Christmas Market (Toronto)
- Cavalcade of Lights (Toronto)
- Holiday Fair in the Square (Toronto)
- Canadian Pacific Holiday Train (Various towns in Canada)
- Light Up the Beach (Toronto)
- The Nutcracker by the National Ballet of Canada (Toronto)
- Winter Wonderland
- Aurora Winter Festival (Toronto)
- Toronto Christmas Concert at Roy Thomson Hall (Toronto)
See these and even more events listed below!
Pickering Holiday Light Displays
Cavalcade of Lights
What to Expect:
Spectacular fireworks display at Nathan Phillips Square
Description:
Toronto's Cavalcade of Lights ignites the city skyline with a dazzling fireworks display. The event centers around the illumination of a massive Christmas tree at Nathan Phillips Square. Visitors can glide across the outdoor ice rink while live music echoes through the square. This Toronto tradition began in 1967 to showcase the city's newly constructed City Hall and has evolved into a beloved annual celebration.
Where: Toronto | More Info: Cavalcade of Lights
Light Up the Beach
What to Expect:
Illuminated boardwalk along Lake Ontario
Description:
Light Up the Beach transforms Toronto's Beaches neighborhood into a twinkling wonderland. The boardwalk along Lake Ontario glows with thousands of lights strung through the trees. Visitors can stroll along the illuminated path, enjoying the crisp winter air and lake views. This event, started in 2007, has become a cherished tradition in the Beaches community, drawing visitors from across the city to experience the lakeside holiday ambiance.
Where: Toronto | More Info: Light Up the Beach
Aurora Winter Festival
What to Expect:
Immersive light displays and winter activities
Description:
Aurora Winter Festival creates a captivating winter experience at Ontario Place. The event features towering light sculptures, an ice skating trail, and a mystical frozen kingdom. Visitors can tube down snow slides or explore a market of local artisans. This festival, which began in 2018, draws inspiration from Nordic winter traditions, bringing a touch of Scandinavian holiday spirit to Toronto's waterfront.
Where: Toronto | More Info: Aurora Winter Festival
Christmas Light Tour
What to Expect:
Self-guided tour of elaborately decorated homes
Description:
Pickering's Christmas Light Tour invites visitors to explore neighborhoods adorned with spectacular holiday displays. Residents compete to create the most impressive light installations, transforming their homes into dazzling spectacles. You can drive or walk through designated routes, marveling at the creativity on display. This community-driven event, which began as an informal tradition, has grown into a beloved annual attraction that showcases Pickering's neighborhood spirit.
Where: Pickering | More Info: Christmas Light Tour
Christmas Tree Lighting Ceremony
What to Expect:
Community gathering to illuminate a giant Christmas tree
Description:
Markham's Christmas Tree Lighting Ceremony brings the community together to kick off the holiday season. The event centers around the illumination of a towering Christmas tree in the city center. Visitors can join in caroling or enjoy performances by local choirs and musicians. This ceremony, which has been a Markham tradition for over 30 years, symbolizes the start of the holiday season and the spirit of community in this diverse city.
Where: Markham | More Info: Christmas Tree Lighting Ceremony
Pickering Holiday Markets and Shopping
Christmas Market
What to Expect:
European-inspired market in the heart of Toronto
Description:
Toronto's Christmas Market brings a slice of European tradition to the Distillery District. Cobblestone streets come alive with wooden stalls offering artisanal crafts and seasonal delicacies. The aroma of mulled wine and roasted chestnuts wafts through the air as visitors explore the market. You can warm up by an open fire while sipping hot chocolate. This market pays homage to the area's Victorian-era architecture, creating a unique blend of old-world charm and modern holiday spirit.
Where: Toronto | More Info: Christmas Market
Holiday Fair in the Square
What to Expect:
Outdoor winter carnival with charitable focus
Description:
Holiday Fair in the Square transforms Nathan Phillips Square into a vibrant winter carnival. The event uniquely combines holiday shopping with outdoor winter activities. Visitors can browse artisanal goods while supporting local charities. Try your hand at axe throwing or enjoy a ride on the carousel. This fair, initiated in 2016, aims to bring the spirit of giving to the heart of Toronto's holiday celebrations.
Where: Toronto | More Info: Holiday Fair in the Square
Holiday Street Market
What to Expect:
Open-air market with a focus on local artisans and food vendors
Description:
Ajax's Holiday Street Market brings together local artisans and food vendors in an open-air setting. The market buzzes with activity as shoppers browse handcrafted gifts and sample seasonal treats. Visitors can watch live demonstrations by local craftspeople or participate in holiday-themed workshops. This event, which began as a small community gathering, has grown to become a significant platform for showcasing Ajax's local talent and businesses.
Where: Ajax | More Info: Holiday Street Market
Pickering Holiday Craft Show
What to Expect:
Showcase of local artisans and handmade crafts
Description:
The Pickering Holiday Craft Show spotlights the talent of local artisans and craftspeople. The event features a wide array of handmade items, from jewelry to home decor. Visitors can watch live craft demonstrations or try their hand at creating their own holiday decorations. This show, which has been running for over two decades, reflects Pickering's strong support for its local creative community.
Where: Pickering | More Info: Pickering Holiday Craft Show
Twilight Tuesdays
What to Expect:
Evening shopping events with extended hours and special promotions
Description:
Twilight Tuesdays in Pickering offer a unique evening shopping experience during the holiday season. Local businesses extend their hours and offer special promotions, creating a festive after-dark atmosphere. Visitors can enjoy live music performances while browsing for gifts or dining at local restaurants. This event, initiated to support local businesses, has become a popular way for residents to connect with their community during the busy holiday season.
Where: Pickering | More Info: Twilight Tuesdays
Pickering Holiday Shows and Entertainment
Canadian Pacific Holiday Train
What to Expect:
Traveling holiday concert on a beautifully decorated train
Description:
The Canadian Pacific Holiday Train rolls across Canada, bringing live music and holiday cheer to communities along its route. This brightly decorated locomotive stops in various towns, where it opens up to reveal a stage for live performances. Spectators can enjoy the concert while contributing to local food banks. Since its inception in 1999, this unique holiday tradition has raised millions of dollars and tons of food for communities in need.
Where: Various towns in Canada | More Info: Canadian Pacific Holiday Train
The Nutcracker by the National Ballet of Canada
What to Expect:
World-class ballet performance with elaborate sets and costumes
Description:
The National Ballet of Canada's production of The Nutcracker dazzles audiences with its grand scale and exquisite choreography. This rendition features stunning sets that transport viewers to a 19th-century Russian winter. You can marvel at the intricate costumes as dancers bring the classic story to life. The National Ballet of Canada has been performing The Nutcracker since 1955, making it a cornerstone of Toronto's holiday cultural offerings.
Where: Toronto | More Info: The Nutcracker by the National Ballet of Canada
Toronto Christmas Concert at Roy Thomson Hall
What to Expect:
Diverse holiday music performances in a world-class concert hall
Description:
The Toronto Christmas Concert at Roy Thomson Hall showcases a rich tapestry of holiday music. The event features performances ranging from classical orchestral pieces to contemporary pop renditions. You can experience the exceptional acoustics of the hall while enjoying both traditional carols and modern holiday hits. Roy Thomson Hall, opened in 1982, has been a cornerstone of Toronto's musical landscape, hosting this beloved holiday concert for decades.
Where: Toronto | More Info: Toronto Christmas Concert at Roy Thomson Hall
A Christmas Carol by Soulpepper Theatre
What to Expect:
Innovative adaptation of the classic Dickens tale
Description:
Soulpepper Theatre's production of A Christmas Carol breathes new life into the beloved Dickens story. This innovative adaptation features creative staging and contemporary musical elements. You can experience the timeless tale of redemption brought to life by some of Toronto's finest actors. Soulpepper, founded in 1998, has become known for its fresh takes on classic works, making this production a unique addition to Toronto's holiday entertainment offerings.
Where: Toronto | More Info: A Christmas Carol by Soulpepper Theatre
Holiday Sing-Along with the TSO
What to Expect:
Interactive concert where audience sings along with the orchestra
Description:
The Holiday Sing-Along with the Toronto Symphony Orchestra invites audience participation in a grand musical celebration. The TSO performs beloved carols and holiday songs, encouraging the audience to join in. Visitors can experience the thrill of singing alongside a world-class orchestra in the magnificent Roy Thomson Hall. This event, which began in the 1990s, has become a cherished tradition, blending the TSO's musical excellence with the joy of communal singing.
Where: Toronto | More Info: Holiday Sing-Along with the TSO
Pickering Other Holiday Activities
Santa Claus Parade
What to Expect:
Community-driven parade with local organizations and businesses
Description:
Pickering's Santa Claus Parade transforms the city streets into a lively procession of holiday cheer. Local organizations and businesses showcase their creativity with elaborate floats, while marching bands fill the air with festive tunes. You can join the crowd lining the parade route, waving to participants and catching candy tossed from floats. This annual tradition dates back to 1953, reflecting the city's long-standing commitment to community celebration.
Where: Pickering | More Info: Santa Claus Parade
Winter Wonderland
What to Expect:
Family-friendly winter activities in a picturesque park setting
Description:
Pickering's Winter Wonderland transforms Esplanade Park into a hub of winter fun. The event features an outdoor skating rink, toboggan hills, and snow sculpture displays. Visitors can participate in friendly snowman-building competitions or warm up by fire pits with hot cocoa. This celebration of winter activities reflects Pickering's commitment to outdoor recreation, a tradition that dates back to the city's early days as a rural community.
Where: Pickering | More Info: Winter Wonderland
Christmas by Lamplight
What to Expect:
Historical reenactment of 19th-century Christmas celebrations
Description:
Christmas by Lamplight at Black Creek Pioneer Village offers a glimpse into 19th-century holiday traditions. The village comes alive with the soft glow of oil lamps and candles. Visitors can participate in traditional crafts or join in caroling led by costumed interpreters. This immersive experience, which began in the 1960s, showcases the rich cultural heritage of Ontario's early settlers and their holiday customs.
Where: Toronto | More Info: Christmas by Lamplight
Victorian Christmas
What to Expect:
Authentic recreation of 19th-century Christmas celebrations
Description:
Victorian Christmas at Toronto's Mackenzie House transports visitors to the 1860s holiday season. The historic home is adorned with period-accurate decorations and staffed by costumed interpreters. Visitors can sample traditional Victorian Christmas treats or participate in 19th-century parlor games. This event provides a unique glimpse into the holiday customs of Toronto's early years, showcasing how the city's diverse population celebrated Christmas in the Victorian era.
Where: Toronto | More Info: Victorian Christmas
Winterfest on Toronto’s Waterfront
What to Expect:
Winter activities and art installations along the lakeshore
Description:
Winterfest transforms Toronto's waterfront into a celebration of the season. The event features interactive art installations, musical performances, and winter-themed activities. Visitors can warm up in cozy fire pit lounges or explore the glowing light sculptures along the shore. This festival, which began in 2019, aims to encourage Torontonians to embrace the beauty of winter and enjoy the city's waterfront year-round.
Where: Toronto | More Info: Winterfest on Toronto’s Waterfront
Santa Train
What to Expect:
Scenic train ride with Santa through the countryside
Description:
The Santa Train in Stouffville offers a unique holiday experience aboard a vintage railway car. The train winds through the picturesque countryside, decorated for the season. Children can meet Santa and his elves while enjoying hot chocolate and cookies. This event, run by the York-Durham Heritage Railway, preserves the region's railway history while creating new holiday memories for families.
Where: Stouffville | More Info: Santa Train
Winter Solstice Celebration
What to Expect:
Multicultural celebration of the year's longest night
Description:
Toronto's Winter Solstice Celebration honors diverse cultural traditions associated with the shortest day of the year. The event features performances and rituals from various cultures, including Indigenous, European, and Asian traditions. Visitors can participate in a candlelight labyrinth walk or join in traditional solstice songs. This celebration, which began in the early 2000s, reflects Toronto's multicultural identity and promotes understanding of different winter holiday traditions.
Where: Toronto | More Info: Winter Solstice Celebration
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