Couple in Pickering enjoying a fun activity at a Christmas Holiday Market


The Joy of Holiday Celebrations in Pickering

‘Tis the season for holiday cheer and festive celebrations! Throughout the city of Pickering, the countdown to Christmas is filled with exciting activities for all ages. From festive markets, wonderful lights, and even Elvis singing Christmas carols, there are tons of activities to do in Pickering this holiday season. There’s no better time to get into the holiday spirit than now, so keep on reading as we delve into Pickering’s joyful holiday celebrations!


Winter Nights, City Lights

Esplanade Park

Friday November 24 & Saturday November 25, 2023


Feel bright and merry in the Winter Nights, City Lights festival at Esplanade Park! Enjoy live entertainment from local performers and carolers and gather around for the Tree Lighting ceremony! You can also admire some of the new art installations, shop at the market tent, and take Insta-worthy pics in front of the tree! With the backdrop of holiday lights and Christmas music, this festival is sure to put you in the holiday spirit!


Santa Claus Parade

Dixie and Glenanna to Pickering City Centre

Saturday, November 25, 2023


Celebrate the holidays with the Santa Claus Parade as it returns to Pickering. Hosted by the City and the Kinsmen & Kinette Club, this year’s theme is “Holiday Storytime.” Enjoy the festive spirit with elaborate floats from Pickering’s businesses and community groups, accompanied by lively marching bands and an appearance of Santa Claus himself! The parade, starting at Dixie and Glenanna and concluding in Pickering’s City Centre, promises to be an exciting celebration, marking the joyful beginning of the holiday season.


Poinsettia Tea

Chestnut Hill Recreation Centre

Sunday, December 3, 2023


Calling all adults 55 and up! Enjoy a festive afternoon tea with Poinsettia Tea! This tea party guarantees a delightful afternoon filled with music, refreshments, and festive joy. Enjoy a live performance by George Lake Big Band and bring home the festive energy with a fresh Poinsettia.


A Christmas Rockstory

Pickering Casino Resort – The Arena

Sunday, December 17, 2023


In the heart of Pickering’s festive celebrations, immerse yourself in the dynamic performance of A Christmas RockStory at the Pickering Casino Resort. This exhilarating show seamlessly blends the rock music with the joy of a Christmas circus.


Be prepared to be amazed by a cast of exceptionally skilled and award-winning specialty acts and acrobats, each contributing to the magic of the performance. From breathtaking acrobatics and captivating aerial stunts to daring feats that keep you on the edge of your seat, these circus performers showcase their exceptional skills in a stunning display of talent.


Wonderful World of Christmas

Pickering Casino Resort – The Arena

Tuesday, December 19, 2023


Enjoy the Wonderful World of Christmas at the Pickering Casino Resort featuring the King of Rock himself, Elvis! From Elvis’ own Christmas classics to holiday favourites, enjoy an Elvis themed festive show with Elvis tribute artist, Steve Michaels.


Register for Pines Ridge today! 

This holiday season, enjoy everything that the city of Pickering has to offer! Is a new home on your wishlist? Embrace the festivities of Pickering and move right into the city’s newest and exclusive community of Pines Ridge. With 45’ & 50’ singles, Pines Ridge is where luxury is defined. Register now for more information!

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