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The holiday season is the perfect time to escape the bustle of the city and discover the charm of nearby small towns. Just a short drive from Kitchener and Waterloo Region, these destinations transform into winter wonderlands filled with twinkling lights, artisan markets, and festive traditions.
Here are four day trips in southern Ontario to add to your holiday break this year:
Elora, Ontario — Ontario’s Prettiest Village
Elora’s cobblestone streets and historic stone buildings make for the perfect holiday backdrop. The Elora Christmas Market lights up the town with thousands of sparkling bulbs, artisan chalet huts, fire tables, and live music. Strolling through Elora feels like stepping into a storybook Christmas village. This magical market runs every Wednesday through Sunday until Christmas. Check out more information on the market’s website: Elora Christmas Market – Ontario’s Spectacular Holiday Destination
Stratford, Ontario — Victorian Christmas Charm
Stratford embraces the season with a mix of old-world charm and lively festivities. The Christmas Trail runs from November 1st through December 20, guiding visitors to local shops offering holiday treats and gifts. Details of the trail and how to purchase vouchers can be found here: The Christmas Trail – Destination Stratford
Santa’s Parade of Lights fills the streets with floats, carolling, and community spirit on December 7 from 5-6:30 p.m. Add in holiday concerts like Christmas with the Ennis Sisters, and Stratford becomes a destination where music and magic meet.
Niagara-on-the-Lake, Ontario — Candlelit Christmas Charm
Few towns capture the magic of Christmas quite like Niagara-on-the-Lake. Its historic main street is lined with heritage buildings draped in garlands, wreaths, and thousands of twinkling lights. Visitors can enjoy festive activities such as horse-drawn carriage rides through decorated streets or the annual Candlelight Stroll through the town accompanied by musical performances on December 5. Find more details here: Events in Niagara-on-the-Lake
St. Jacobs, Ontario — Holiday Village Charm
St. Jacobs is known for its warm small town charm and during the holidays it shines even brighter. The St. Jacobs Farmers’ Market is the perfect cozy backdrop for checking off your shopping list with local artisan vendors and seasonal treats. The Market also offers plenty of holiday events including Storytime with Santa. All the event details can be found here: 2025 Events | St.Jacobs Market
The village streets are also decorated with lights and garlands, and visitors can enjoy cozy shops, delicious treats, and the perfect blend of holiday shopping and small-town charm.
As the holidays draw near, these small-town escapes remind us that the season’s magic isn’t just in the lights and decorations, but in the joy of exploring new places with family and friends. Whether you choose Elora, Stratford, Niagara-on-the-lake, or St. Jacobs, each offers its own festive traditions and cozy charm — perfect for making memories that last well beyond the holidays.
Staebler Insurance is wishing you all a charming and festive holiday season!
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