Image Description: A bundled-up adult and child hold hands while ice skating at Springer Market Square, Kingston. The child, in a tan parka with a fluffy white hat and bright pink gloves, skates beside the adult, who wears a light-colored winter coat, red beanie, and white skates. In the background, other skaters enjoy the rink in front of historic stone buildings dusted with snow, creating a cozy winter city scene.
Image Source: https://downtownkingston.ca/pages/embrace-the-season
Downtown Kingston turns winter into an invitation: bundle up, head downtown, and treat the colder months as a reason to explore, not hibernate. From twinkling lights and skating under the sky to cozy wagon rides and passport-style shopping adventures, it’s designed to make the city’s core feel like a festive village all winter long.
Winter magic in the heart of Kingston
Winter downtown centres on Springer Market Square, where the historic limestone backdrop, holiday lights, and seasonal decor create a postcard-perfect setting for both everyday outings and special events. The square doubles as a hub: you can skate, sip something hot by the firepits, wander over to shops and cafés, then circle back for more music and lights as evening falls. This year I plan on doing ice skating and when the rink is open, skating becomes the heartbeat of the season, with extended hours that make it easy to fit in a glide before work, after class, or as a spontaneous date night. Rentals from local outfitters mean you do not need your own skates to join in, lowering the barrier for visitors, new residents, and anyone rediscovering winter after a long break.
Cozy rides, lights, and small-town charm
Part of the magic comes from how you move through downtown. Horse-drawn wagon rides offer a slow, almost storybook way to see the streets. Free trolley rides add a playful, practical twist: hop on, warm up, and let the bright red trolley shuttle you between shops, restaurants, and the square. These rides do more than move people; they frame the entire area as a shared experience
Shop local, win prizes, feel connected
Programs like the Holiday Shopping Passport and The Downtown Holiday Advent Calendar turn gift-buying into a kind of adventure, where every small purchase earns a stamp, an entry, or a surprise waiting behind an advent-style reveal. As you wander, you may stumble into pop-up workshops, artist showcases, or stores offering free samples and gift wrapping, making it easy to linger instead of rushing through a list. Free Saturday parking in select downtown areas removes one of the most common barriers to spending time in the core, quietly nudging more people to stay, stroll, and say yes to one more café or shop.
Whether you are a long-time Kingstonian or new to town, downtown becomes a place to rewrite your relationship to cold weather and trading complaints for cozy layers, bright lights, and shared moments you will actually look forward to next year.