It is 1900, and 14-year-old Bertie McCross is a newspaper boy in downtown Toronto. Bertie's family has fallen on hard times and can use every penny he brings home from hawking newspapers on the frigid streets. However, in order to do that Bertie has to keep out of the clutches of the Kelly Gang, a family of slightly older Cabbagetown toughs who are shaking down "newsies."

On Christmas Eve, Bertie is almost cornered by the Kellys but is saved by Tommy Fry and Milwaukee Ed, who introduce Bertie to the thrills of iceboat racing on Lake Ontario. Soon Bertie is swept up in the fast and dangerous sport and meets a whole crew of new friends, including Isobel, a girl from a wealthy family with a mansion on Jarvis Street. The continued pursuit by the Kelly Gang, a plunge into freezing harbour water, and the clash of classes all lead up to a spine-tingling race to end all races.