Winter in downtown Kingston has its own kind of magic. From festive parades, fun shopping programs to outdoor adventures, it’s the perfect place to Embrace the Season.

Picture yourself snuggled up on a horse drawn wagon ride, embarking on the ultimate holiday shopping adventure, or meeting Santa himself in Springer Market Square. Every day in downtown Kingston holds a bit of magic waiting to be enjoyed.

We've put together a list of 11 ways you can embrace winter and celebrate the season in downtown Kingston!

Start your holiday shopping in style this winter with special offers and festive activities all around downtown! With over 30 participating locations planning workshops, giving free samples, featuring local artists and offering exclusive shopping deals there’s plenty to explore and enjoy.

Treat yourself to free gift wrapping, take a cozy horse-drawn wagon ride, and make sure to scan the ornaments at each stop for a chance to win a $500 Downtown Kingston Gift Card. Happy holiday hunting!

Make your holiday shopping downtown even more rewarding this season with the Holiday Shopping Passport! Pick up your passport at any participating location, and every purchase of $10 or more brings you closer to winning up to $5,000 in Downtown Kingston Gift Cards.

It’s a fun, festive way to support local businesses while scoring big and making holiday shopping a little more magical!

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Santa Claus is coming to town! Join the festive fun as the Nighttime Santa Parade makes its way down Princess Street, filling downtown with holiday cheer. The excitement builds to a magical grand finale, where Santa himself will light the tree in Springer Market Square!

Experience the joy of daily holiday surprises from downtown’s best shops, spas, restaurants, and hotels! Stop by the giant holiday calendar in Springer Market Square and scan for a chance to win fantastic prizes every day from your favorite local spots.

Each day reveals a new opportunity to win huge prizes, from spa treatments and gourmet dinners to unique items and luxurious hotel stays.

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The Coca-Cola Holiday Caravan is rolling into downtown Kingston! This iconic red truck, decked out in sparkling lights and carrying the world-famous Coca-Cola Santa, is bringing a festive experience like no other. Join us for joyful holiday music, capture unforgettable family photos with Santa himself, and soak up the excitement

Come meet the jolliest guy in town! Santa Claus himself will be posing for festive photos with holiday merrymakers on Brock Street outside City Hall during Santa Saturdays! And because Santa adores animals, feel free to bring your furry friends along for the fun!

Shop in style this holiday season aboard the iconic red Kingston Trolley! With just one stamp on your Holiday Shopping Passport, you can hop on and enjoy a cozy ride to all your favorite stops downtown.

Trolley Stops:

• Casa Domenico - 35 Brock Street
• The Works - 298 Princess Street
• The Grand Theatre - 218 Princess Street
• The Toucan - 76 Princess Street

Make your holiday shopping experience easier, more festive, and uniquely Kingston!

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Embrace the winter season in downtown Kingston with a scenic ride on a cozy horse-drawn wagon! Snuggle up and take in the holiday lights and bustling charm of the historic streets from a whole new perspective.

Pick Up and Drop Off:

• Market Street beside Springer Market Square (1 Market St.)

Wrap up your holiday shopping and get everything on your wish list in downtown Kingston! Enjoy festive activities like scenic horse-drawn wagon rides, visits with Santa, and free trolley rides through the heart of downtown. With special deals, seasonal cheer, and family-friendly fun, it’s the perfect way to finish your shopping while embracing the holiday spirit!

It's the most wonderful time of year, Pewter Season! From November 18th through December 16th, a new pewter ornament inspired by Kingston’s iconic architecture and landmarks will be released every Monday. In celebration of the 30th anniversary, this year’s collection will feature a blend of beloved ornaments from past years along with exciting new designs.

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Skate in one of the oldest market squares in Canada as you take in the beautiful historic view of Downtown Kingston. Warm up with a Beavertail and hot chocolate around the firepits in the square after you skate for the perfect winter day or evening.

Don’t have your own skates? You can rent a pair from Trailhead for $12 (overnight) or for $10 (3 hours). 

As a special gift from the Downtown Kingston Business Community, in partnership with the City of Kingston parking in downtown surface lots and on-street parking will be FREE on Saturdays from Nov. 30th to Dec. 21st

*Please note* Free parking does not apply to the Chown and Hanson parking garages. Free parking only applies to on-street parking and City of Kingston surface lots within the downtown Kingston boundary.