On the evening of November 20, the Downtown Oakville BIA will light the holiday tree in Towne Square, in the corner of Lakeshore Road East and George Street, with Santa on hand and participating shops open late. It will look like every other year's ceremony. It will also be the last one held in the square as it stands today. The town's construction schedule for the square's $7.5-million revitalization was built so that this night could go ahead, with a four-month construction pause starting in November.
That pause shapes the downtown calendar through September 2027. Knowing the stage dates tells you which storefronts are fenced this month, why most winter events are moving a few blocks north, and why George Street will act as a substitute square next summer.
The Pause Was Written Around One Evening
Plans to redesign Towne Square go back to 2017. Oakville News reported that the project was shelved when bids came in over budget, then held up by the wider downtown reconstruction and by COVID-19. The last version of the timeline would have started work in January 2026 and finished by November 2026, in time for this year's tree lighting.
Council paused that plan in October 2025. The restaurants around the square, Hexagon among them, said 11 months of noise, fencing and limited access would cost them a full patio season. Much of the schedule is driven by the waterproofing membrane on top of the condo parking garage beneath the square, which has to be replaced. In that same report, Oakville News quoted Ward 3 councillor Janet Haslett-Theall speaking to council:
"We know Towne Square is your Towne Square as well. We ask for your indulgence and patience while we find the optimal solution to support our businesses through another revitalization, and hope to get to a better place soon."
The answer came at a special council meeting on May 26, 2026. Council approved an "Optimal Phasing Plan" along with a cost-sharing agreement with Brosko. Under the plan, staff moved the storefront work so that restaurant patios could stay open through the end of September 2026. The fall work goes one frontage at a time, then stops for the holidays. The schedule's own notes say the over-winter pause is "built in to protect the holiday season."
This Fall Moves One Storefront at a Time
The idea behind the plan is that only one tenant, or a small group, takes the full brunt of active construction at any given time. Here is the fall sequence as the May schedule laid it out:
- Stage 1, September 2 to 23: Soontorn Bahn Thai and Raymond James frontage
- Stage 2, September 24 to October 11: 7Enoteca frontage, east side
- Stage 3, October 13 to 26: Hexagon frontage, south side
- Stage 4, October 27 to 29: Burrows Clothiers frontage, northwest corner
- Stage 5, October 30 to November 9: Towne Square Gallery frontage, west side
- Stage 6, November 2026 to February 2027: over-winter pause, no construction
Treat those dates as the plan, since they were never firm. Staff called the schedule a best case, because no one knows what repairs the garage slab needs until the old waterproofing comes off. The real start date also moved. Oakville News reported in September that work was tentatively set to begin during the week of September 14, roughly two weeks after the September 2 start in the stage table. If every stage slid back by the same amount, the Gallery frontage would wrap up somewhere around November 21 to 27, after the tree lighting. On that slower timeline, November 20 would come before the winter pause begins. The May schedule had the pause starting first.
The town has said that businesses in an active construction zone stay open and accessible. Staging and worker parking were moved off-site to ease congestion downtown. Staff's mitigation plan also keeps the underground garage elevator open 24/7, and extended work hours are limited to when they are needed.
The BIA has two events in the square before the pause. On October 31, Tiny Tots runs from 10 a.m. to noon at participating downtown businesses, and Tails & Treats takes over Towne Square at 1 p.m. On the May schedule, that afternoon falls during the west-side Gallery stage, so expect part of the square's edge to be fenced off while the dogs come through.
November 20 Is the Old Square's Last Big Night
During the pause, the site stays in what the schedule calls a "temporary transition condition," with access to every tenant maintained all winter. The detailed plan says the square will stay open for the holiday season, tree lighting included.
The BIA confirmed it. According to Oakville News, the annual Holiday Tree Lighting stays at Towne Square for 2026, and the BIA plans to hold its other winter events at Centennial Square, 120 Navy Street. The BIA's Light Up The Night page lists 5 p.m. on November 20, with holiday lighting along the downtown streets, a visit from Santa, the tree lighting in Towne Square and late hours at participating shops. More details are still to come.
The split is the practical part. The tree lighting is the one holiday night anchored at Lakeshore and George. For the rest of the season, the downtown's public events move north to Centennial Square on Navy Street, and the BIA's Hometown Holiday page hasn't posted that lineup yet. If the 2027 schedule holds, next year's tree lighting will be in the rebuilt square.
February to September 2027: George Street Becomes the Event Space
The bigger disruption comes after the holidays. Stage 7, the central plaza, is scheduled to run from February 9 to August 2, 2027. All tenants are affected during those six months, four public entrances stay open, and the main construction entrance is off Robinson Street.
That is why George Street matters next year. Oakville News reported that the section of George Street between Lakeshore Road East and Church Street will close from spring 2027 until construction ends in September, so it can host downtown events and activities next summer where possible. The CIBC parking lot and Municipal Lot 3 stay accessible. The May staff report had already named George Street as an alternate event space.
Patios come back before the plaza work is done. The phasing comparison targets April 2027 for patio access, and it notes that construction hoarding will still be up when the patios first reopen. The last stages go back to individual storefronts in late summer, ending with Leela Eco Spa from August 3 to 16 and the Paul Vincent Hair frontage from August 24 to September 16. Leela Eco Spa expects modified hours during its stage.
| Period | What the square is doing |
|---|---|
| Fall 2026 | One frontage fenced at a time, square still in use |
| November 20, 2026 | Tree lighting in the current square |
| Winter 2026 to 2027 | No construction; other BIA winter events at Centennial Square |
| February 9 to August 2, 2027 | Central plaza under construction |
| Spring to September 2027 | George Street closed and used for events |
| April 2027 | Patio access returns, behind hoarding |
| September 2027 | Target completion, best case |
What the Finished Square Adds
According to the town's description, the rebuilt square will have amphitheatre-style seating for gatherings and events, a water feature, raised planters and seating areas, new trees and landscaping, an updated central lawn, decorative lighting and new accessible paving. Amphitheatre seating suits the square's role as the downtown's main event space, which is the same role the schedule is working to protect.
On cost, the May staff report says the extra consultant, phasing, hoarding, event and communications costs fit within the existing $7.5-million capital budget. The phasing-package comparison estimates the Optimal option itself at $7.06 million. Town staff have said they will keep working with local businesses, residents and community partners throughout construction so people stay informed. The slab is the main unknown. Until the waterproofing comes off, staff can't say whether the September 2027 finish will hold.
If you own near Lakeshore and George and want to know how a fenced square this winter and a rebuilt one in 2027 could affect your home's value, Nancy Kohli Haté can walk you through it using current downtown Oakville sales. Request a complimentary home valuation.
