Celebrate the holiday season with a magical night of holiday shopping in downtown Kingston! Discover over 20 local businesses offering festive deals, giveaways, and fun holiday activities.

Enjoy free trolley rides, horse-drawn wagon rides, and find special stickers at each location for a chance to win a $500 Downtown Kingston Gift Card. Make this season unforgettable with shopping, treats, and festive fun in the heart of Kingston.

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!

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 favourite 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.

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. Enjoy joyful holiday music, capture unforgettable family photos with Santa himself, and visit with the Kingston Frontenac's beloved mascot, Barrack the Bear!

Experience the magic of the holidays at Santa’s Village in Springer Market Square! Santa Claus will be there for Santa Saturdays, posing for festive photos with kids, families, and even pups. Capture a joyful holiday moment with the man in red and make this season unforgettable.

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 favourite stops downtown.

Trolley Stops:

• De Mello Coffee (33 Brock Street)
• Pizza Studio (Barrie Street at Princess)
• The Grand Theatre (218 Princess)
• The Toucan (76 Princess)

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

The 5th Annual Mitten Tree Drive invites families to enjoy horse-drawn wagon rides, photos with Santa in Santa’s Village, a Christmas letter writing station, and cozy firepits with s’mores, all available with a donation. Guests are encouraged to bring new or gently worn winter clothing or a cash donation to support the Welcoming Streets program.

Hosted by Revel Realty Kingston, this family-friendly event is a joyful way to celebrate the season while giving back to the community.

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 and the City of Kingston, parking in downtown surface lots and on street will be free on Saturdays from December 1 to December 21 to brighten your holiday shopping season.

Parking, as always, is free every Sunday, along with Christmas Day and Boxing Day.

*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.