Kerr Village's Holiday Season Starts on Two Saturdays, Two Weeks Apart

Kerr Village's holiday season begins twice this month. On Saturday, November 14, the Town of Oakville's Santa Claus Parade sets the schedule. Kerr Street becomes part of a route shared with downtown, and the morning is planned around it. Two Saturdays later, on November 28, the Kerr Village business improvement area runs its own afternoon. It holds a tree lighting and holiday market at Westwood Park, at the corner of Kerr and Bond streets, as it has for more than 30 years.

The two days work differently, so they need different plans. One is a short, early, Town-wide procession that closes streets. The other is a long, slow afternoon that ends in the dark, on the neighborhood's own park lawn.

November 14: The Town's Morning on Kerr Street

The Oakville Santa Claus Parade starts at 9:00 a.m. on Saturday, November 14. Visit Oakville expects it to wrap up around 10:30 a.m. and lists its location as "Downtown Oakville and Kerr Village." This year's theme is North Pole sweets and treats. The Kerr Village BIA's events page lists the parade as running from 9 to 11 a.m. The parade marked its 77th anniversary last year, so this is the 78th, and the Town runs it with a council-led parade committee. Last year's committee chair was Ward 7 Councillor Scott Xie, according to the Town's 2025 announcement published in Oakville News.

The parade is over by mid-morning. Visit Oakville warns that people who arrive later in the morning may miss part of it.

The Santa Shuttle

Oakville Transit runs a free Santa Shuttle from Oakville GO Station. It leaves every 5 to 10 minutes, goes straight along Dorval Drive to Trafalgar Park Community Centre with no stops in between, and runs from 8:00 to 11:30 a.m. Return shuttles to the GO station also stop at 11:30. The shuttle's drop-off point is in Kerr Village, so on parade morning more people arrive in the neighborhood than in any other week of the year.

What the Closures Looked Like Last Year

The Town posts its closure list for the November 14 parade on its service-disruption notices page. The 2025 list shows what Kerr Village can expect. Oakville News reported that closures ran from 6:00 a.m. to noon along the route, with no local access through the affected areas. These were the Kerr Village closures on that 2025 list:

• Kerr Street between Lakeshore Road and Stewart Street
• Stewart Street between Kerr Street and Maurice Drive
• Felan Avenue between Stewart Street and Rebecca Street
• Deane Avenue between Maurice Drive and Kerr Street
• Rebecca Street between Dorval and Forsythe Street, as an emergency access route

Last year's detour routes were Chartwell Road, Cornwall Road, Speers Road, Dorval Drive and Fourth Line. In 2025, the closures began three hours before the parade did, so anyone on those blocks needed to move their car before 6:00 a.m. Speers Road, along the north edge of the village, was a detour route rather than part of the parade.

The Rest of the Day Moves to Speers Road

When the parade ends, the day's other Kerr Village event is already underway a few blocks north. Film.Ca Cinemas at 171 Speers Road holds its Christmas Market the same Saturday, from 10:00 a.m. to 4:00 p.m.

The timing works because the market opens an hour after the parade starts and keeps going well past the noon end of last year's closures. Vendors set up only in the cinema's carpeted and tiled lobby, and every vendor spot is sold out. Film.Ca's page lists three things for families coming from the parade:

1. Free movies playing on the morning of November 14.
2. Visits with Santa in the lobby, among the vendors.
3. Free rides on the Cinema Express electric train in the parking lot, from 10:30 a.m. to 3:30 p.m.

That makes November 14 a full day in two parts. The Town's parade fills the morning on the Lakeshore end of Kerr Street, and a neighborhood movie house fills the afternoon at the Speers end.

The Week Downtown Lights Its Tree First

Six days later, downtown holds its tree lighting. Light Up The Night takes place on Friday, November 20, at Towne Square, 94 George Street, from 5:00 to 9:00 p.m. The tree is lit at 6:00 p.m., Santa visits, and participating shops stay open late.

That puts eight days between downtown's tree and Kerr Village's. Kerr Village holds its lighting on the last Saturday of November, in its own park, at its own pace. The parade connects the two business districts for one morning. The tree lightings keep them on separate dates.

November 28: Kerr Village's Own Afternoon at Westwood Park

The 2026 Kerr Village Christmas Tree Lighting & Holiday Market takes place on Saturday, November 28, at Westwood Park, 173 Kerr Street, from 1:00 to 6:00 p.m. The listing notes that Kerr Village has held a Christmas tree lighting for more than 30 years and that the event has grown over that time. Last year's event was billed as the 31st annual, which makes this year's the 32nd.

The parade is done by late morning. The tree lighting runs for five hours and finishes at dusk. Last year's schedule, reported by Oakville News, shows how the afternoon was paced in 2025:

The 2025 event also added a covered stage for the performers and a mobile health team offering free flu shots. Children could drop off letters to Santa.

The Two Traditions That Stay the Same

Two parts of the event have been described as recurring. According to Oakville News, "as in previous years," the local Tim Hortons hands out free coffee, hot chocolate and treats. The event also collects donations for Kerr Street Mission's Christmas Wonders and beyond outreach program. The 2025 event page described the whole afternoon as a free event held in support of Kerr Street Mission, with donations accepted. The charity and the sponsor both come from the same few blocks, and so does the event.

The Two Saturdays Side by Side

On November 14, Kerr Street is part of the Town's parade route for the morning. On November 28, the event happens at the corner of Kerr and Bond, run by the businesses that line that street. To see Kerr Village's own tree lit, be at Westwood Park by 5:30 p.m. on the 28th, the time the ceremony started last year.

The streets that close for the parade and the park that fills two weeks later are part of what living on these Kerr Village blocks means. At Robertson Kadwell, we follow the neighborhood's calendar as closely as its sales. If you would like to know how your home compares in today's Kerr Village market, request your complimentary home valuation, and we will walk you through it before the tree goes up.