Oakville Holiday Events in November 2026: Parades, Tree Lightings and Markets

The holiday calendar in Oakville starts well before December. Visit Oakville has pulled together what is on this month, and there is something nearly every weekend from here to the end of November.

The Oakville Santa Claus Parade steps off at 9 a.m. on Saturday, November 14 through downtown Oakville and Kerr Village. Oakville Transit runs a free Santa Shuttle from Oakville GO to the Trafalgar Park Community Centre lot every 10 minutes starting at 8 a.m. The same day, Film.ca Cinemas holds its annual Christmas Market at 171 Speers Road, 10 a.m. to 4 p.m.

Light Up the Night takes over downtown on Friday, November 20 from 5 to 9 p.m., with carollers, horse drawn carriage rides, hot chocolate and the Towne Square tree lighting at 6 p.m. Bronte follows on November 21 with At Home in Bronte for the Holidays at Market Square, where the tree goes on at 5:30 p.m., and Kerr Village lights its own tree at 5:30 p.m. on November 28.

The markets keep coming. The Bronte Historical Society's Christmas Art Show is at Sovereign House on November 21, Local Love sets up at Verace on November 25, and November 28 brings the Appleby College Holiday Market, where there is skating as well as vendors, so bring your own skates and helmet and leave the sticks at home. The Oakville Art Society holds its art market that weekend too, and 41 vendors fill the Holiday Inn Oakville Centre on November 28 and 29.

The Oakville Museum has two of its own: a Christmas craft and guided tour on November 27, and a Santa visit on November 28 that starts with a letter at Oakville's First Post Office and ends in his sitting room at Erchless Estate. Times and addresses for everything are on Visit Oakville.