Discover beloved signature winter events & free family activities in Downtown Kingston.
Experience the Magic of Winter in Downtown Kingston.
Experience the Magic of Winter in Downtown Kingston
Discover beloved signature winter events & free family activities in Downtown Kingston.
Downtown Kingston Winter Events & Activities
Celebrate the snowy season in Downtown Kingston with an action-packed lineup of events and activities.
Festive Friday Holiday Shopping Crawl
Friday, November 14th
5:00 PM to 8:00 PM
Participating Locations
Celebrate the season with a magical night of holiday shopping in downtown Kingston! Explore over 20 local businesses featuring festive deals, giveaways, and fun activities. Enjoy free trolley rides, horse-drawn wagon rides, and scan the special stickers at each stop for your chance to win a $500 Downtown Kingston Gift Card.
Nighttime Santa Parade & Tree Lighting Ceremony
Saturday, November 22nd
5:00 PM to 7:00 PM
Princess Street & Springer Market Square
Santa Claus is coming to town! The Nighttime Santa Parade will fill Princess Street with lights, music, and holiday magic starting at 5 PM. The celebration continues with the grand finale at 7 PM, when Santa lights the tree in Springer Market Square!
Free Downtown Trolley Rides
Saturday, December 6th, 13th, 20th
11:00 AM to 3:00 PM
+ Festive Friday, November 14th
5:00 PM to 8:00 PM
Step aboard the iconic red Kingston Trolley and shop in style this holiday season. With just one stamp on your Holiday Shopping Passport, you can ride in comfort to your favourite downtown stops.
Trolley Stops:
- De Mello Coffee (33 Brock Street)
- Pizza Studio (Barrie Street at Princess)
- The Grand Theatre (218 Princess)
- The Toucan (76 Princess)
Santa Saturdays
Saturday, December 13th & 20th
12:00 PM to 2:00 PM
Springer Market Square
Meet the jolliest guy in town at Santa’s Village in Springer Market Square! Stop by to say hi, snap a festive photo, and make a holiday memory to treasure. Kids, families, adults, and even pups are all welcome!
Downtown Holiday Shopping Programs
With unique shops and festive holiday programs, there’s no better place to shop for the season than downtown.
Holiday Shopping Passport
Holiday Shopping Passport
Do your holiday shopping downtown this season and score big with the Holiday Shopping Passport! Grab a Holiday Shopping Passport at a participating location starting November 14th, start shopping, and you could win up to $5000 in Downtown Kingston Gift Cards.
Giant Holiday Advent Calendar
Giant Holiday Advent Calendar
The Downtown Kingston Holiday Advent Calendar is back! From December 1st to 24th, discover gifts and prizes from over 30 local shops, restaurants, spas, and hotels. Visit the giant holiday calendar in Springer Market Square, scan, and enter for your chance to win amazing prizes from your favourite downtown spots.
Pewter Mondays
Pewter Mondays
It’s Pewter Season! From November 17th to December 15th, a new ornament inspired by Kingston’s landmarks will be released each Monday. Grab yours for $10 at the Visitor Information Centre, Grand Theatre, or Slush Puppie Place with $25 in downtown receipts dated after November 1, 2025.
A Winter Day Downtown
Downtown is packed with magical winter fun every day this season.
Skate the Square
Lace up and hit the ice for Kingston's premier winter experience! Day or night a spin around the Springer Market Square Skating Rink is a magical moment unlike anything else in the city. Don't have skates? Make your way up Princess Street to Trailhead Kingston and rent the perfect pair.
Gather 'round the Fire
After a long skate, chase away the chill with your favourite people around a cozy wood-burning fire pit. Rest your feet, get comfy in bright red Adirondack chairs, and embrace the warmth.
Sip Hot Chocolate
The cherry on top of a perfect winter day skating and shopping downtown is a cozy cup of hot chocolate. Especially when it's paired with a BeaverTail or two. With cafés on practically every corner, you won't have to look far to find that sweet spot.
Find The Perfect Bite
Skating, shopping and sipping sweet warm drinks will work up an appetite. Try something new or indulge in your favourite classic cravings at one of the many delicious restaurants downtown and discover the perfect bite.
Capture the Moment
You won't find a prettier background than snow-covered downtown Kingston. Say cheese over a delicious plate of food or get the perfect group shot around the fire. And don't forget to show your followers your skate routine.
Skate the Square
Lace up and hit the ice for Kingston's premier winter experience! Day or night a spin around the beautiful Springer Market Square Skating Rink is a magical moment unlike anything else in the city. Don't have skates? Make your way up Princess Street to Trailhead Kingston and rent the perfect pair.
Gather 'round the Fire
After a long skate, chase away the chill with your favourite people around a cozy wood-burning fire pit. Rest your feet, get comfy in bright red Adirondack chairs, and embrace the warmth.
Fire Pits are lit Thursdays and Fridays: 6pm to 9pm, Saturdays: 12pm to 8pm, and Sundays: 12pm to 5pm
Sip Hot Chocolate
The cherry on top of a perfect winter day skating and shopping downtown is a cozy cup of hot chocolate. Especially when it's paired with a BeaverTail or two. With cafés on practically every corner, you won't have to look far to find that sweet spot.
Find the Perfect Bite
Skating, shopping and sipping sweet warm drinks will work up an appetite. There are so many delicious options downtown anyone can discover the perfect bite. Kingston restaurants are putting their best on display this winter with mouth-watering prix fixe menus and irresistible culinary events for Visit Kingston's Kingstonlicious!
Capture the Moment
Downtown Kingston is the place to make memories and capture them! Say cheese over a delicious plate of food or get the perfect group shot around the fire. And dont forget to show your followers your skate routine. You'll discover plenty of selfie spots all across downtown and you won't find a prettier background than snow-covered Kingston.
Share your Winter Experience
We want to see how you embraced the season in downtown Kingston!
Tag us @downtownkingston to be featured in our stories!
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