by Bri Mitchell | November 2023

Waterloo Region is full of romantic date ideas for the holiday season.

In fact, there are so many things for you and your partner to do that we’ve created a holiday road trip itinerary just for this special time of year!

This road trip itinerary brings you to two different but cozy accommodations, and covers the ground from the quaint village of St. Jacobs, to the town of New Hamburg, to the city of Cambridge – so your adventure will be a little bit country, with plenty of urban adventures in between.

Day 1 – Arriving in a Winter Wonderland

Start out by heading to your accommodation for night one.

Puddicombe House is a charming and historic mansion located in the town of New Hamburg. This 1868 restored home features 8 romantic rooms, each one designed with comfort and luxury in mind. It’s a wonderful escape from the hustle and bustle of big cities and will allow the two of you to enjoy some quiet time together. Spoil yourself even further and book a treatment at Puddicombe’s onsite salon and spa! The restaurant at Puddicombe is casual fine dining in an elegant atmosphere where you can warm up over a late dinner. Consider sharing so you can try more dishes, like a wood-fired pizza, a creamy Butternut Squash Agnolotti, or Braised Beef Short Ribs.
Insider Tip:  If you’re looking for a unique dining experience, book a table in advance in one of Puddicombe’s outdoor winter greenhouses! Each greenhouse has its own private heater to keep you both warm and cozy: it will feel like you’re dining in your own private snow globe!

If you’re arriving on a Friday and feel like a little holiday shopping, head to the Sip ’n ’Shop evening event at the St. Jacobs Farmers’ Market – Canada’s largest year-round market. Check out all the vendors and find a cute gift for one other, or get a little holiday shopping done while sipping on warm festive beverages. Make sure you get your ticket in advance to secure your spot!

Day 2 – A Sleigh Ride Together

Wake up Saturday morning and say farewell to Puddicombe House. Head across the street to MeMe’s Café & Food Shop in New Hamburg for a delightful cup of coffee and a pastry. Their to-go menu rotates weekly at MeMe’s, so you can be sure that there will be something new and exciting to try no matter when you visit. They’re well known for their bagels and breads on Saturdays, which will be the perfect fuel for your next activity.

From MeMe’s, it’s off to St. Jacobs for a romantic sleigh ride with St. Jacobs Horse Drawn Tours. Private sleigh rides can be reserved in advance, and their small-sized sleigh is perfectly roomy for two. Make sure you dress in extra layers and bring your gloves, hat and scarf. It would even be a good idea to bring a festive blanket to cozy up under as you head through open fields and the tall maples in the sugar bush!

After a romantic time out on the sleigh, head into the Village of St. Jacobs. It’s a lovely place to visit at any time of year, but during the holidays St. Jacobs truly shines. Enjoy authentic sights, sounds, smells, tastes, and incredible one-of-a-kind shopping in boutique shops decked out for the holidays. You’ll feel like you’ve stepped back in time as you watch Mennonite horse and buggies make their way through the village!

There are lots of great places to grab a bite to eat in St. Jacobs, including the Village Biergarten and Jacob’s Grill. You can also raise a glass to each other at Block Three Brewing – a craft brewery dedicated to creating interesting and unique beers.
Insider Tip: Try their Fickle Mistress or King Street Saison – two local favourites!

Once the sun goes down, it’s take to light things up! Bingemans in Kitchener offers two amazing light displays – one that you can enjoy from the comfort of your car, and one that the two of you can stroll through together. Gift of Lights is a drive through display featuring over 300 animated and static light displays and light tunnels. Jingle Bell Rock is a walk through wonder of giant light sculptures, musical animations and a 40 foot Christmas tree. It’s perfect for capturing a special picture of the two of you as you enjoy your holiday adventure!

Whenever the timing is right for you, check in at your accommodation for Saturday night: The Laundry Rooms in the new Gaslight District in Cambridge. The Laundry Rooms are trendy apartment style accommodations that offer a convenient location right in the heart of the holiday action. Feel free to check in any time, park your car, and enjoy their incredible amenities!
Insider Tip: If you’re feeling hungry, or want to relax with a beverage before turning in, both Foundry Tavern and Foundry Brewing Co. are located in the Gaslight District and are easily walkable.

Day 3 – Wrap it Up

Take your time waking up on Sunday, and treat yourself to a little lazy morning sleep in.

Your only goal this morning is to enjoy a late brunch at either Foundry Tavern (their Funky Brunch takes place every Sunday from 10am to 3pm) or the Cambridge Mill (with its beautiful views overlooking the Grand River).

After your brunch, why not spend a few hours at the Gaslight District Christmas Market? This outdoor market is perfect for picking up a few final gifts for loved ones (or each other!) before heading back home.

There’s one final stop to complete your romantic holiday road trip in Waterloo Region. The historic West Montrose Covered Bridge will be decorated with festive wreaths for the holiday season – and maybe even some mistletoe. The ‘Kissing Bridge’ (as it’s also known) is the perfect place for one last picture of the two of you – the perfect souvenir of your romantic getaway!


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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