Get Your Jingle On! 2023 Holiday Happenings in Waterloo Region

UPDATED November 2023

It’s in the air – colder temperatures, the appearance of snowflakes, and a feeling that lets you know the holidays have arrived in Waterloo Region!

Ready to get your Jingle on? Here’s a list of things to do to get the festive fun started.

**Know of other holiday happenings going on in Waterloo Region? Share them with us on social using the hashtag #ExploreWR **

Holiday Fun in Waterloo Region

St. Jacobs Sparkles November 16-19 & 23-26
Come shop into the night amid thousands of twinkling lights in the village and take in the holiday festivities and entertainment! Santa has even set up a satellite Workshop in the village where on special dates and times you can see him at work and drop off your letter to Santa.

Gift of Lights & Jingle Bell Rock at Bingemans November 17 – January 6, 2024
Bingemans offers two ways to take in beautiful holiday light displays! Enjoy the lights from the comfort of your car at Gift of Lights – a family-friendly drive-thru holiday light display with two tunnels and over 300 animated and static light displays! Meanwhile, Jingle Bell Rock is a walk-through light display that includes spectacular walking tunnels, sparkling lighting decorations, and a breathtaking 40′ lit up Christmas Tree. You can also relax at the open fire pits with some s’mores, and decorate cookies in Mrs. Claus’ Kitchen. Advance Tickets are recommended.

Castle Kilbride ‘Christmas at the Castle’ November 15 – January 7, 2024
Step back and marvel at the sights and sounds of a merry Victorian Christmas. At Castle Kilbride, they take a whole lot of old and a little bit of new and mix it together for the perfect holiday setting. This is the best time of year to visit the 1877 home of the Livingston Family and marvel at the lavish décor adorned in festive attire.

Waterloo Central Railway Santa Trains November 18 – December 23
Choose from a daytime or nighttime holiday train adventure with Waterloo Central Railway’s Santa’s Countryside Ride and Santa’s Christmas Caboose trains. Bring your family and friends and get ready to head to the North Pole! With stories, your favourite Christmas characters, and a visit from the Man in Red himself, this unique holiday adventure will put sparkles in the eyes of children of all ages.

Sip ‘n Shop Night Market November 17, 24 and December 1
The St. Jacobs Farmers’ Market offers 3 Night Markets just in time for the holidays! Indulge in some retail therapy and savor an assortment of festive beverages specially crafted to add a touch of warmth and merriment to your shopping spree. Whether you’re searching for that special something or just treating yourself, this event promises a delightful selection of one-of-a-kind finds.

Cambridge Winterfest November 23 – December 31
Cambridge Winterfest features a number of seasonal events including Phil Klein’s Unsilent Night, a visit from the CPKC Holiday Train, Winter Ice and Lights, the Cambridge Christmas Market, Music and Lights in the Village, and winds up with a New Year’s Eve Party!

Dog Friendly KW Paw-liday Festival | December 2

The DFKW Paw-liday Festival returns to Downtown Kitchener, a hyper-local festive holiday market with all kinds of activities and entertainment for you, your dog, and your family! The festival includes workshops, a kids’ craft station, photo pop-ups, festive food and drinks, and more. And, you can shop for the 4-legged members of your family at more than 24 different vendors.

A King Family Christmas at Woodside National Historic Site December 2 & 3
Join the Kings for a Victorian Christmas event for the whole family! Warm yourselves with roasted chestnuts cooked by an outdoor fire, then head inside the historic Woodside home to dress the family Christmas tree. Join in festive games and activities and see for yourself how Victorian-era families celebrated this special time of year. Please come dressed for the weather.
Woodside National Historic Site is the boyhood home of William Lyon Mackenzie King, Canada’s tenth and longest-serving Prime Minister

Winter Campfires at Snyder’s Farm Weekends Only November 25 – December 17
Gather ’round the fire with your family or a group of friends at Snyder’s! Your fire will be lit and stoked before you arrive – just sit and enjoy great company in the beautiful winter countryside. Each campfire includes a S’mores kit, and you have the option to order hot dog roasting kits, gourmet pizzas, nachos and bakery desserts. The Sweets & Spirits Bar will also be open so you can raise a glass of holiday cheer and toast the holidays! Campfires Experiences must be booked in advance.

Christkindl Market December 7-10
Wilkommen to Christkindl Market! For 4 days in December, downtown Kitchener transforms into a traditional German Christmas market. Enjoy a cup of hot chocolate and listen to Christmas carols while strolling around the twinkling lights of the market. With over 75 vendors selling traditional handcrafted items, live music, dance performances, and unique holiday-themed craft activities for children, Christkindl Market is sure to become your favourite family holiday tradition!

UpTown Waterloo Winter Wonderland Dec. 1-3
Uptown Waterloo hosts a variety of special holiday events for you to explore! Join in the Tree Lighting Ceremony on December 1, shop at the Holiday Pop-Up Artisan Market, and take a self-guided tour throughout Uptown Waterloo to discover beautifully painted themed windows by local artists at various businesses. Don’t forget to pop by Mistletoe Lane with your special someone – be sure to grab a holiday selfie!

Wintery Crafternoons December 3, 9, 10, 16, 17
Historic Schneider Haus is holding its family friendly Wintry Crafternoons every weekend in December from 12 until 4 pm to celebrate the winter season!
These Crafternoons are included in the price of admission, enjoy a wonderful craft and tour of this National Historic Site in its coziest season!

Community Carol Sing in Ayr December 10
Save the date! This popular carol sing is back and takes place outdoors in Centennial Park in Ayr. Make sure to dress for the weather, and get ready to sing some of your favourite holiday tunes!

Starry Night December 16
Enjoy the sights of a Christmas past as you wander through the village at the Waterloo Region Museum in its finest lantern-lit beauty. Stroll down the paths and experience the unique ambiance of a historic village holiday celebration. Enjoy sweet treats as you sip hot apple cider while under the twinkling stars. The evenings’ music, food, and good cheer will surely get you and your family in the holiday spirit. Don’t forget your camera, as we will have a special guest visiting for a great holiday selfie.

Ticket holders will also receive an exclusive behind-the-scenes virtual tour showcasing the historic buildings in Doon Heritage Village, and the traditions and stories inside.

Winter Sleigh Rides with St. Jacobs Horse Drawn Tours
Looking for a fun and memorable activity to do with your family? A scenic Sleigh Ride through open fields and the tall sugar bush is just the thing! These are private bookings and require reservations in advance.