Plan Your Holiday Weekend Road Trip to Waterloo Region

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by Alex Kinsella | November 2022

There’s something special in the air this time of year in Waterloo. From snow-covered trees decorated with holiday lights to the aroma of mulled wine and hot apple cider, winter is the perfect time for a weekend road trip to explore the cities and townships of Waterloo Region. Whether you’re visiting for the day or taking a much-needed weekend getaway, we have fantastic events, unique shopping, and delicious culinary experiences ready to explore.

Dog Friendly KW Paw-liday Festival

November 26–27

You don’t have to leave your pup at home during your holiday weekend road trip to Waterloo Region. The first-ever Dog Friendly KW Paw-liday Festival is taking over Downtown Kitchener for two days of live music, trick competitions, puppy yoga, and more. It’s the perfect event for dog owners, dog lovers, and families.

Insider tip: Book your stay at the Delta Hotel in Uptown Waterloo if you’re bringing your dog to Waterloo. They’re a pet-friendly hotel steps away from shops, restaurants, and an ION light rail transit station. Ready for something to eat? It’s not a traditional holiday meal, but locals confirm that no visit to Waterloo is complete without trying the raja stuffed peppers at Ethel’s Lounge.

Holiday Sip’ n Shop Night Market

December 2

The St. Jacobs Market District attracts visitors from across Canada and around the world for its fantastic array of local makers, foods, and craft breweries and cideries. The St. Jacobs Farmers’ Market is great for a daytime visit, but this year, you can experience the market at night with its Holiday Sip’ n Shop Night Market. Enjoy some holiday cheer as local breweries and distilleries serve up delicious drinks, find that perfect final decoration to deck your halls with, and enjoy a cozy fire while listening to talented local artists.

Insider tip: If you’re staying for the weekend, check out the St. Jacobs Market District hotels, including the Courtyard by Marriott and the Hampton Inn and Suites. These hotels are located within walking distance of the Market and just a short drive off Highway 85 and the 401, putting you in the centre of everything Waterloo Region offers.

KWFamous Holiday Pop-Up Shoppe

November 30 – December 30

Weekend getaways to Downtown Kitchener are full of experiences you won’t forget, from theatre and concerts to shopping. This year, you can shop from over 80 local makers and creators at the KWFamous Holiday Pop-Up Shoppe at 165 King St. W. across from Kitchener City Hall. KWFamous is a local group of young creatives who program pop-up events across Waterloo Region, including its first pop-up roller rink last summer! This winter, KWFamous invites you to discover unique gifts for friends, family, or yourself, all while supporting the local artist and maker community in Waterloo Region.

Insider tip: Great shows are going on throughout December at Centre in the Square, including concerts by the Kitchener-Waterloo Symphony, a performance of Swan Lake by the State Theatre of Ukraine, and one of our favourites—Marie Osmond on December 1. If you’re looking for somewhere to escape the crowds, head to the Sugar Run, our local speakeasy (the password is “Larry Johnson,” but don’t tell anyone else!) After a busy day of shopping, sipping and shows, book a relaxing weekend stay at the historic Walper Hotel in Downtown Kitchener.

Jakobstettel – Celebrate 170 Years of St. Jacobs

November 24–December 18

2022 is the 170th anniversary of St. Jacobs, and the community is celebrating with Jakobstettel, a series of events for locals and visitors alike. Throughout November and December, the village – located along the Conestoga River – is the place to shop and dine. St. Jacobs Sparkles is an annual holiday shopping event featuring thousands of twinkling lights throughout the village, providing a festive backdrop as you explore the shops, restaurants, and bars of St. Jacobs. You can also experience a nighttime Christmas lights train ride on the historic Waterloo Central Railway. This hour-long ride takes you from the Farmers’ Market Station all the way to the North Pole and back, while Christmas characters and the Jolly Old Elf himself join you for the ride!

Insider tip: It may be cold outside, but in St. Jacobs you can still enjoy craft beer and great food outdoors at one of the heated domes at the Village Biergarten. Book your dome—each one seats up to eight people—in advance for a night outside you won’t soon forget. And check out the newly opened Fat Sparrow Block, too, for their fantastic selection of wine and charcuterie.

Christkindl Market

December 1–4

The one event not to miss this winter in Waterloo Region is the return of the Christkindl Market in Downtown Kitchener. This year marks the first in-person market since 2019, and we’re ready to welcome you back to our traditional German Christmas market. Enjoy a cup of hot chocolate or mulled GlĂĽhwein 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 the perfect event to include in your holiday getaway itinerary to Waterloo Region!

Insider tip: Check out the Christkindl Market from high above the city at the KWFamous Jingle Bar. It’s a rooftop pop-up bar with hot toddies, games, and more on that takes place on Saturday, December 3.

We’ll see you in Waterloo Region!

This is just a sample of what you can experience in Waterloo Region this winter. Check out our complete listing of holiday happenings in Waterloo Region—we’re looking forward to hosting you!


Alex Kinsella is a freelance writer and marketer based in Waterloo Region. He’s the guy behind TL;WR â€“ Waterloo Region’s weekly events newsletter. He’s worked with some of Canada’s most well-known tech companies in roles including customer success, development, product management, PR, social media and marketing.

Alex has contributed to publications including BetaKit, Grand Magazine, Community Edition and more. Follow him on Twitter and Instagram.


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