Magical Holiday Train Rides in Toronto for 2026

As the leaves start to turn and the air cools, it’s time to embrace the magic of the holiday season in Toronto. This year, the city is offering a variety of festive train rides that will delight families and digital nomads alike. From twinkling lights and carols to visits from Santa, here are some of the most magical holiday train experiences you won’t want to miss.

CPKC Holiday Train | Toronto
Join the annual CPKC Holiday Train tradition, which will be rolling into Toronto on the evening of November 29, 2026. The train will be covered in thousands of lights and feature a free concert with Tyler Shaw and the American Authors. While you can’t board the train, you can enjoy the performances from a specially designed stage. This event is free, but donations are encouraged for local food banks. The train will be on display from 8:30 p.m. to 9 p.m. at 750 Runnymede Rd., Toronto.

The Redpath Express | Harbourfront Centre
Transform your holiday experience with The Redpath Express, part of the HarbourFrost celebrations at Harbourfront Centre. Enjoy a train ride surrounded by twinkling lights and seasonal decorations. The train will run Fridays, Saturdays, and Sundays from November 20 to December 20, with evening rides on Fridays and Saturdays. The event is free, no tickets needed. Stop by Harbourfront Centre at 235 Queens Quay W., Toronto.

North Pole Express | Railway Museum of Eastern Ontario
Step into a world of wonder as you board the North Pole Express at the Railway Museum of Eastern Ontario. This magical train ride features festive decor, carols, and visits from Santa. The museum is located in nearby Kingston, Ontario, but the experience promises to be a highlight of the holiday season. Check their website for specific dates and times.

These holiday train experiences are a fantastic way to celebrate the festive season in Toronto. Whether you're a longtime resident or a digital nomad just passing through, there’s something for everyone. So, bundle up, grab your camera, and get ready for a magical journey!