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.

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. While you're there, enjoy free horse-drawn wagon rides for even more holiday fun downtown!

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.

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

Get ready to soak up the festive spirit at the James Brett Coiffure Christmas Market! Their space will be filled with local makers sharing jewelry, holiday crafts, decor, glassblowing, textiles, paintings, crochet, and so much more! Enjoy some cozy holiday cheer while you find unique gifts and support local makers!

James Brett Coiffure will also be open for retail shopping with great year-end savings, so you can pick up something special while you're there.

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!

Please note: This does not apply to regular Kingston Trolley Tours

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 Gift Certificates to Downtown Kingston businesses.

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!

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). 

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!

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.

Learn More

Holiday shopping downtown feels extra special during the colder months, and programs like the Holiday Shopping Passport make it easy to turn your visit into a full winter outing. These seasonal traditions return each year, giving you a simple rhythm to follow as you enjoy winter activities at your own pace.

Start your day with a warm cup of cocoa or a seasonal latte from a cozy café, then stroll along downtown streets lined with colourful displays and wintery decor. With your Passport in hand, you can explore local boutiques and shops offering apparel, gifts, and treats.

Here’s an easy flow you can follow each season:

• Visit key shopping streets filled with unique finds, festive windows, and inviting storefronts.

• Use your Downtown Kingston Gift Card to pick up meaningful gifts from neighbourhood shops.

• Take a break with a snack or local brew, letting the wintery atmosphere set the tone.

• Collect Passport stamps as you go, turning your outing into a chance to win huge gift prizes!

Nothing says winter like enjoying a warm, rich hot chocolate (or any hot bevvie) while you explore the snow-covered streets of downtown. And lucky for you, there's no shortage of options to choose from!

If you're enjoying a skate around Springer Market Square, warm up with a sweet drink from De Mello Coffee, Kingston Coffee House, M & J Cakes & Cookies, or BeaverTails.

If you're moving up and down Princess St, taking care of your holiday shopping, then make sure to stop by CRAVE, Coffee & Company, Columbus Café & Co. or Balzac's.

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: Excludes all garages and the Ontario/Brock lot. Free parking only applies to on-street parking and City of Kingston surface lots within the downtown Kingston boundary.