The Bentway Skate Trail

The Bentway Skate Trail is a masterclass in urban reclamation, transforming the neglected, concrete-heavy space beneath the Gardiner Expressway into a vibrant winter destination. Since its inception, this 220-meter figure-eight trail has become a quintessential Toronto experience, where the city’s industrial grit meets the joy of outdoor skating. Weaving between the massive highway pillars, the atmosphere is undeniably cool, especially at night when the lights illuminate the ice and the surrounding architecture. It is deeply connected to the Fort York neighbourhood, acting as a bridge between the historic site and the modern high-rises of CityPlace. It feels less like a traditional community rink and more like a deliberate, artistic intervention that forces you to appreciate the city’s unique infrastructure while you glide.

For a first-timer, the best approach is to go during the weekday evenings after the initial holiday rush to avoid the heaviest crowds. Entry to the trail is free, but keep in mind that rentals and concessions are strictly cashless—bring your debit or credit card. If you don't have your own skates, you can rent them on-site, though you will need a valid government-issued ID and must sign a waiver. While there is a concession stand for hot drinks and snacks, don't expect a full meal; plan to grab dinner in nearby CityPlace or Liberty Village afterward. Check their website before heading out, as hours fluctuate throughout the season, and keep an eye out for special events like the Polar Bear Skate if you are feeling particularly brave.