A Magical Holiday Family Road Trip to Waterloo Region

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by Bri Mitchell | November 2023

Beautiful wide-open spaces to explore – twinkling festive lights in city centres – snow, skating and s’mores….

If you are on the hunt for the perfect family getaway road trip this season, look no further than Waterloo Region. There are so many magical places and experiences that deck themselves out for the holidays, and are very much on the family friendly side of things this season.

So gather the family, pack your bags, and get ready to make memories that will last a lifetime!

Day 1 – O’er the Fields we Go!

The car ride to Waterloo Region is definitely part of the festive experience! Take the route less travelled and meander through the Region’s townships: these back roads are where you’ll start to feel the magic as you take in expansive fields, pastural farmscapes, and snow-covered trees.
Insider Tip: take time to stop along the way and explore one of the Region’s many trails – it’s a great way to enjoy the outdoors together and get some fresh air as you start exploring!

There are plenty of hotel options in Waterloo Region. However, for a unique experience, check out Leisure Estates Bed and Breakfast Retreat – a 4-season retreat tucked in the countryside close to the charming village of Elmira. There are hiking trails on site, a 1900’s style barn, and plenty of room in the modern, main house (most guest rooms can accommodate up to 4 or 5 people). Curl up around the fireplace, and enjoy their full breakfast with homemade baking – yum!

Once you’re checked in you can spend the night enjoying the amenities at Leisure Estates. Or, if the family still has the energy, why not head out to grab a bite (big appetites will love Crowsfoot Smokehaus in nearby Conestogo, while Those Pizza Guys in St. Jacobs offer delicious, wood-fired pizzas). Then, step out into the night and take in two holiday light experiences – Gift of Lights and Jingle Bell Rock at Bingemans. For families with younger kids, Gift of Lights is a drive through experience – a perfect way for younger kids to drift off to sleep while watching the bright holiday light displays! If you’re looking for an extra excuse to stretch your legs after dinner, Jingle Bell Rock lets you walk through giant light sculptures, musical animations and a truly breathtaking 40 foot twinkly tree centerpiece.

Once you’ve lit up the night, head back to your room for a good night’s sleep so your ready for Day 2!

Day 2 – All aboard!

After a restful first night in Waterloo region, take your holiday celebrations to the St. Jacobs area on Saturday.

Storytime with Santa at St. Jacobs Farmers’ Market is a fun morning activity for the whole family which takes place on 2 Saturdays in December. Listen to Santa read magical Christmas stories out loud, and then decorate your own special homemade cookie, straight from the north pole. Then, spend some time exploring Canada’s largest year-round farmers’ market. With 100’s of vendors, you’ll not only find amazing fresh produce, you’ll also discover unique gift ideas – perfect for getting a head start on your holiday gift list!

Continue the holiday fun with more adventures with Santa in the afternoon. After grabbing a delicious lunch at the St. Jacobs Farmers’ Market, take an historic Waterloo Central Railway adventure with Santa’s Countryside Ride. This ride takes place throughout the months of November and December, and offers families a magical ride filled with festive carols, Christmas crafts, a holiday dance party, and a visit from Santa! If you’re looking to spread the holiday cheer into the evening, then hop aboard Santa’s Christmas Caboose at night for a festive, light-filled ride on an historic train car covered in Christmas lights. Both of these experiences in the snowy Waterloo countryside are guaranteed to awaken that magical glint in the whole family’s eyes.

Top off the magic of the day by seeing a performance of Peter Pan: The Panto at the St. Jacobs Country Playhouse. This annual show plays throughout the months of November and December, with matinee and evening showtimes, perfect for families of all ages. Pantos are fun for the entire family, as the audience is encouraged to cheer for the good guys, boo the bad guys, and immerse themselves into the fun!

Day 3 – Brunch, Bakeries and Butterflies – Oh My!

The final day of this family weekend road trip starts by setting your sights in and around Cambridge.

Start the day with a delightful breakfast or brunch at Café du Monde Creperie. With a delectable selection of sweet and savoury crepes and other offerings, this is an excellent place to ease into the day as a family.  
Insider Tip: If you’re feeling extra festive, make sure you pick up one of their DIY Holiday Tree Cookie kits. Take it home to decorate and display just in time for all of the holiday festivities at home! 

With full bellies, it’s time for experience the warmer side of the holidays! Cambridge Butterfly Conservatory is a wonderful excuse for the whole family to take their coats off for a while and catch their breath surrounded by the magic of thousands of butterflies flitting about this balmy, tropical space. Note that timed tickets must be purchased in advance of your visit and can be purchased through the website.

For lunch or a sweet treat, head to Sugar Daddies Bakery. The kids will love all the goodies they offer – while parents will appreciate that all of the baked goods at Sugar Daddies Bakery are gluten-free, keto-friendly and yes – even sugar-free! Not only do they have delicious baked treats, but their lunch and dinner options are a dream come true, too!

Cap off this magical holiday weekend by checking out Winter Ice an Lights – part of the Cambridge Winterfest festivities. There are beautiful light displays in Central Park, as well as light installations throughout Cambridge (you can take your own self-guided tour). If your road tip happens to take place on the second weekend in December, you can also head to the Cambridge Christmas Market. This award-winning market offers unique gifts, seasonal food and a great shopping atmosphere – it takes place both Saturday and Sunday in downtown Cambridge.

With so much magic sprinkled throughout this family weekend, the kids will remember their enchanting holiday road trip to Waterloo Region for weeks and years to come!


About Bri Mitchell 

Bri was born and raised in Ontario. She spent many years living abroad, but returned to the province with a curiosity to keep travelling closer to home. 

You can find her canoeing and swimming across Ontario with a craft brew in her hand in the summer, and snowshoeing or curling up with a good book and an Ontarian Pinot Noir in the winter. 

She loves writing about travel experiences in our beautiful province and beyond on the websites travelingmitch.com and ultimateontario.com.


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