Festivals and Events

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: 2231 Nursery Road, Springwater (Midhurst). American Authors and Tyler Shaw are expected on this part of the tour. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Monday, November 30, 2026, 12:30 PM to 12:55 PM.

Downtown Regina kicks off the holidays with tree lightings in Victoria Park (6:00 PM) and at City Hall (6:30 PM), visits with Santa and the Grinch, live local performances, a holiday farmers' market in the City Hall cafeteria, horse drawn wagon rides between hubs and free hot chocolate. Thursday, November 19, 2026, from 5:00 PM to 8:00 PM. The City of Regina calls it a free, family friendly event.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: CPKC railway crossing on Nashville Road, near the old grain elevator, Vaughan. American Authors and Tyler Shaw are expected on this part of the tour. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Monday, November 30, 2026, 10:15 AM to 10:45 AM.

Winnipeg's big Santa Claus Parade rolls through downtown along Portage Avenue, with block parties along the route beforehand. Saturday, November 14, 2026: block parties from 4:00 PM, parade at 5:00 PM. It is a public parade on city streets, so anyone can watch for free; check the parade's website for the route and road closures.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: CPKC yard office parking lot, 750 Runnymede Road, Toronto. American Authors and Tyler Shaw perform. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 8:30 PM to 9:00 PM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: 680 Laval Drive, behind Walmart, Oshawa. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 3:15 PM to 3:45 PM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: Scugog Road and Wellington Street, Bowmanville. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 2:00 PM to 2:30 PM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: East of the railway crossing on Prince Edward Street, Brighton. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 11:45 AM to 12:15 PM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: RCAF Road railway crossing, Trenton. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 10:45 AM to 11:15 AM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: West of the storage facility on Keegan Parkway, Belleville. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Sunday, November 29, 2026, 9:30 AM to 10:00 AM.

Free outdoor holiday concert on a stage built into the lit up CPKC Holiday Train. Where: Wilson Street railway crossing, Perth. American Authors and Tyler Shaw are expected on this weekend's stops. Bring non perishable food or a money donation for the local food bank if you can. Arrive early: the show lasts about 30 minutes. Saturday, November 28, 2026, 8:00 PM to 8:30 PM.

Western's salsa band Los Gansitos plays its fall concert at The Spoke cafe in the UCC building. Tuesday, December 8, 2026, 8:00 PM to 9:00 PM, at University Community Centre (UCC), Western University. Western lists it as free, with no cover charge.