Downtown Oakville's holiday tree will be lit at 6 p.m. on Friday, Nov. 20, at Towne Square, the centrepiece of Light Up The Night. The evening kicks off the holiday season downtown and runs from 5 to 9 p.m., with Lakeshore Road East between Thomas and Dunn streets turned into a car-free pedestrian street for the night.

Drivers should plan around a much longer window than the party itself. The road closures run from 1 to 11 p.m. that Friday, and George Street between Church Street and Lakeshore Road East closes too. The Town says there will be no local access inside the closed area, so anyone who usually drives through that block will need to go around; the detour uses Thomas, Church and Dunn streets.

The event is put on by the Downtown Oakville BIA, the business improvement area that represents shops and restaurants in the downtown core. This year the tree stays in Towne Square even though the square is in the middle of a makeover. The Town says the BIA's lighting will remain there for the 2026 season.

The redevelopment is being done in phases. The first runs from September to November, and construction is set to pause for the holiday season from November until early 2027. The Town has budgeted $7.5 million in total for the project.

The BIA's schedule starts with DJ Jan at 5 p.m., followed by The Ault Sisters and a live band at 5:30. After the tree goes up in lights at 6, City Dance Corps leads dance lessons at 7 p.m., and the Candy Cane Carollers take over at 7:30.

Organizers also advertise horse-drawn wagon rides leaving from George and Robinson streets, on a first-come, first-served basis. Visit Oakville's listing says participating shops will stay open late.

Downtown's is one of several neighbourhood kickoffs. Bronte Village holds its annual tree lighting the next day, Saturday, Nov. 21, at Market Square, with the tree lit at 5:30 p.m. Kerr Village follows on Saturday, Nov. 28, with its 32nd annual tree lighting and holiday market.

Downtown's own holiday programming continues with Hometown Holiday Cheer, running from 2 to 6 p.m. on Dec. 5, 6, 12, 13, 19 and 20.