Downtown Kingston gets festive with 2023 holiday shopping events

Santa Claus in downtown Kingston. Photo by Catarinia de la Mora.

Downtown Kingston is full of delights this December — offering holiday shoppers a flurry of fun-filled activities, including Festive Fridays, Stop and Shop Saturdays, a Holiday Shopping Passport, a giant Holiday Advent Calendar filled with amazing gift ideas and daily prizes, and maybe best of all: free parking!

For the next four Saturdays (Dec. 2, 9, 16 and 23) parking on-street and in downtown surface lots is free from 11 a.m. to 3 p.m. According to a release from the Downtown Kingston Business Improvement Area (BIA), this is a “special gift from the downtown Kingston business community,” and runs in partnership with the City of Kingston.

The BIA shared the following details on the holiday events taking place from now until Christmas.

Running Friday evenings (Dec. 1, 8, 15 and 22) from 5 to 8 p.m., Festive Friday is the best time to make your list and check it twice. Many shops will be offering customer appreciation treats, entertainment and promotions. Getting through your shopping list on both Festive Friday and Stop & Shop Saturday is easier with free Holiday Trolley rides, or snuggle up together on a free horse-drawn wagon ride. And when the shopping is done, grab a hot drink and sink into a large Muskoka chair around a roaring firepit in Springer Market Square.

Photo via Downtown Kingston.

Pick up a Holiday Shopping Passport at any participating business for a chance to win one of four weekly draws for a $500 Downtown Kingston Gift Card or the grand prize of a $3,000 Downtown Kingston Gift Card. Make a purchase of $10 or more at a participating business and receive a special sticker to fill the passport. When the passport is complete, submit it at a participating business, or take a picture of your passport, and submit it online. According to the BIA, the gift card can be used at over 120 downtown businesses.

And just when you thought you were done, the BIA invites everyone to stop by Sydenham Street where you could win daily prizes with the giant Holiday Advent Calendar. Discover 24 days of gifts from your favourite downtown shops, restaurants, salons and spas. A new gift will be revealed each day leading up to Christmas, and it could be yours!

All event details, including Trolley and horse-drawn carriage stops and timings, as well as contest information available at

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