Canadian Pacific Holiday Train, Oconomowoc

The Canadian Pacific Holiday Train returns to downtown Oconomowoc this December for a festive free show. This beloved annual tradition brings live music and holiday cheer right to your community, with performer Allen Stone entertaining families at the Silver Lake Street crossing. The show runs for about 30 minutes, so plan to arrive early to claim a good viewing spot. Keep in mind that trains often run behind schedule, so bundle up and come prepared to wait—bring snacks, water, warm drinks, and plenty of winter layers. This is more than just entertainment; it's a chance to support a great cause. The Canadian Pacific Holiday Train raises funds and food donations for local food banks, and the Oconomowoc Area Food Pantry will be collecting donations throughout the event. You'll find volunteers stationed at multiple collection points around the viewing area, plus St. Paul's Church will be selling hot cocoa and cookies. Portable restrooms are available nearby, and if you need help or want a safe meeting spot, the Fire District command station at Silver Lake Plaza is there for families. Best of all, there's no admission cost—just bring your family and your generous spirit.