Historic Christmas at Pickering Museum Village

‘Twas the Night Before Christmas: Holiday Events & Performances Across the Region

Posted : November 9, 2022

Our blog is chock full of great ideas for fun things to see and do in York Durham and Headwaters. We are always adding new content and updating old posts, but sometimes you might stumble upon something from our vault. If this article has inspired you to hit the road, be sure to double-check that the featured stops in this post are still welcoming visitors.

Tis the season for sugar plum faeries to regale us all in stories of the magic of Christmas!

Let your heart be light as you explore all of the incredible holiday events taking place across York Durham Headwaters! Sprinkled across the region is a long list, fit for Santa himself, of jolly good entertainment to help get you in the Christmas spirit!

Pickering Museum Village

Historic Christmas at Pickering Museum Village

Explore the Pickering Museum Village this holiday season with their enchanting A Storybook Christmas experience! Visitors can enjoy this self-guided walking tour of the village with the help of their very own keepsake storybook. Let yourself be transported to a Christmas village with seasonal music, crafts, treats, and more! Plus, be prepared to meet ole Saint Nick himself!

The fun doesn’t stop there! Another fun holiday experience at the Museum is the Polar Plushie Workshop! As the perfect accompaniment to A Storybook Christmas this workshop lets you live out childhood dream as being one of Santa’s elves. Become toymaker for a day and build your own stuffed plush polar bear toy. You’ll even get to design a t-shirt for them to wear!

Theatre Orangeville

Theatre Orangeville Couple

Enjoy a full belly chuckle at the Orangeville Theatre with a performance of The Last Christmas Turkey. If you’re looking for something beyond the classic Christmas plays, The Last Christmas Turkey is a refreshing alternative.

Based on Dan Needles book by the same name, the story is about two young siblings that take in an abandoned turkey. However, that turkey’s fate is up for debate. Along with some enchanted animal friends they all set off on a memorable journey.

This adaptation includes 15 songs by Clive VanderBurgh. It all comes together to create a lovely and laugh inducing musical that’s fit for the whole family!

Regent Theatre

Oshawa’s Regent Theatre

Visitors can find a ton of Christmas entertainment at Oshawa’s Regent Theatre! The theatre hosts a comprehensive list of all the best holiday concerts, plays, and movies in Durham region!

Children will love spending a night out at with the classic movie, The Polar Express. Along with a fun Christmas comedy play the Regent Theatre is showcasing an awesome line up of concerts throughout November and December that will make Santa proud.

A Christmas Spectacular starring Pete Paquette, and a wealth of other talent, will bring all your favourite Christmas songs to the stage. Your heart will fill with joy as you sing along to all the best holiday classics like Bing Crosby’s ‘White Christmas’ and Elvis Presley’s ‘Blue Christmas.’

The award-winning Canadian tenor, John McDermott, is returning for his always popular family Christmas concert. In addition, The Barra MacNiels bring their lively East Coast energy, performing Christmas classics that will get you dancing in your seats.

FLATO Markham Theatre


A great venue that’s close to Toronto to indulge in some traditional holiday performances is the FLATO Markham Theatre.

Sit back in one of their classic red theatre seats and take in the Nutcracker! Created by the celebrated director Jörgen, this beloved favourite is a must-experience in the region!

For those looking for a light-hearted show this holiday season then grab a pair of tickets to O Christmas Tea: A British Comedy. This wildly funny and entertaining show is reminiscent of iconic British comedies like Monty Python and Mr. Bean. Discover how this duo stays afloat after their Christmas tea party floods the world in tea!

Who can resist singing along to the songs of Christmas? The FLATO Markham Theatre also has a few performances to prepare your lungs for caroling. With shows like A Swingin’ Christmas with Toronto All-Star Big Band, A Very Merry Motown Christmas, and Elvis: Wonderful World of Christmas, there’s something for everyone!

York Durham Heritage Railways

 York Durham Heritage Railway

All aboard, next stop – The North Pole! Yes, you and your family can board the historic York Durham Heritage Railways train with the magical destination being the North Pole. The heated heritage train is making various tours this holiday season.

On the North Pole Light UP Express, families will enjoy Christmas stories told by Mrs. Claus as well as some of Santa’s friends. Cups with chocolate milk and cookies make this trip even sweeter! But that’s not all! There’s a tree lighting and even gifts from Santa too!

Families will have their pick of delightful Christmas train rides! There’s also a Santa Express Train and a delicious Pancake Breakfast Train to the North Pole! Indulge in some of Mrs. Clause’s tastiest recipes and sing carols with Santa!

Step back in time and raise your glasses for a Victorian Christmas Tea. Step right up and be dazzled by the holiday decorations! You can sit back and sip to your merry heart’s content as the winter wonderland that is the Oak Ridges Moraine rolls by your window.

You can also dig in for a four-course Christmas meal aboard the train! There’s a catch! This adult only evening includes a murder mystery that’s reminiscent of the Orient Express with a side of Elf! With live music, full bellies and a naughty elf in the mix, this is the perfect weekend escape!

Richmond Hill Centre for the Performing Arts

Richmond Hill Centre for the Performing Arts

The timeless story of the Nutcracker has warmed the hearts of generations every Christmas! And York Region is delighted to have two presentations of this holiday classic. One of which can be seen at the Richmond Hill Centre for the Performing Arts.

Audiences will be swept away by this astounding tale of a girl and a nutcracker who comes to life on Christmas Eve! Prepare to be all aflutter with jingle bells as you are transported to a magical world through the art storytelling through ballet.

Nothing will get you in the spirit of the season quite like The Nutcracker!

The Caledon Townhall Players


In the Village of Caledon audiences have been relishing in live theatre at the Old Townhall for over 50 years! Set in an over 145-year-old building you can enjoy one of the sweetest theatre productions in Headwaters.

The story, A Christmas Tail, is an endearing family comedy about a butcher, a young girl and a Christmas Eve miracle. It’s a must-see this holiday season to help put you in the ultimate Christmas spirit!

So, don your best Christmas sweater, grab a hot apple cider and get ready for Christmas in York Durham Headwaters!

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