Lakeshore Road East between Thomas Street and Dunn Street will be closed to cars on Friday, Nov. 20, for Light Up The Night, the downtown holiday kickoff. The Downtown Oakville BIA, the business improvement area that represents shops and restaurants in the downtown core, runs the event from 5 to 9 p.m. and is turning that stretch into a pedestrian street for the evening, the BIA says.
The centrepiece is the annual tree lighting in Towne Square at 6 p.m. The Ault Sisters and a live band take the stage at 5:30 p.m., with dance lessons at 7 p.m. and carolling at 7:30 p.m. Participating shops will stay open late and Santa will visit, according to Visit Oakville, the town's tourism site.
Horse-drawn wagon rides leave from George and Robinson streets on a first-come, first-served basis. Strolling carollers and hot chocolate round out the night.
Drivers should plan around a longer window than the party itself. The Town's road closure runs from 1 to 11 p.m. that Friday and also takes in George Street between Church Street and Lakeshore Road East, the Town says. Local access inside the closed area will not be maintained, and traffic is detoured along Thomas, Church and Dunn streets.
Gift shoppers can stay downtown for the weekend. The Oakville Art Society holds its Art of Giving show and sale at 260 Lakeshore Road E on Saturday, Nov. 21, from noon to 5 p.m. and Sunday, Nov. 22, from 11 a.m. to 5 p.m. Work by local artists will be on display and for sale at accessible prices, with refreshments for visitors.
The society runs the sale in partnership with Zezza Collia Realty Group and takes a 20% commission on each sale of art and cards.
West of downtown, Bronte Village holds its own annual tree lighting on Saturday. At Home in Bronte for the Holidays runs from 3 to 7 p.m. in Bronte's Market Square, with the tree lit at 5:30 p.m., Visit Oakville says.
Kerr Village is next, with a tree lighting and holiday market on Saturday, Nov. 28, from 1 to 6 p.m., a tradition Visit Oakville says goes back more than 30 years. Then Holiday Lights by the Lake fills Coronation Park with lights from Friday, Dec. 4, into February 2027.
| Event | Date | Time | Where |
|---|---|---|---|
| Light Up The Night | Friday, Nov. 20 | 5 to 9 p.m. | Lakeshore Road East, Thomas to Dunn |
| Art of Giving show and sale | Saturday, Nov. 21 | Noon to 5 p.m. | 260 Lakeshore Road E |
| Art of Giving show and sale | Sunday, Nov. 22 | 11 a.m. to 5 p.m. | 260 Lakeshore Road E |
| At Home in Bronte for the Holidays | Saturday, Nov. 21 | 3 to 7 p.m. | Market Square, Bronte |
| Kerr Village Tree Lighting and Holiday Market | Saturday, Nov. 28 | 1 to 6 p.m. | Kerr Village |
| Holiday Lights by the Lake | Dec. 4 to February 2027 | Coronation Park |






