Cheers Caledon is part of Celebrate Caledon, a weekend of fun, friendship and community in Caledon, Ontario. Cheers Caledon starts things off on Friday night. Saturday morning is Vélocity – a charitable bike ride in support of Caledon seniors. And then at 2:00 p.m. on Saturday Caledon Day begins. Caledon Day is the Town’s largest free, family-focused, fun event of the year, attracting over 13,000 visitors.