Dark, chilly evenings have a way of turning bright and warm at community gatherings. Downtown Oakville will usher in the festive season in full regalia on November 20th, when locals and visitors don their cozy apparel and head downtown for Light Up The Night.
This long-standing event absolutely dazzles, thanks to the generosity of the businesses of Downtown Oakville. Featuring live music, dancing, and the lighting of a 45-foot holiday tree, โtis the seasonโs most highly anticipated family outing, date night, solo stroll or hangout with friends.
Due to the popularity of Light Up The Night, a street closure will be in place on Lakeshore Road East between Thomas and Dundas Streets to create a pedestrian-friendly area around the event site.
At the centre of it all is, of course, the tree. Maker of memories, bringer of joy, this spectacular specimen sets the tone for a joyous winter by enfolding the community in its green, forest-scented embrace. But how does it happen?
Generous helpings of skill, collaboration, and holiday spirit go into feats of such magnitude. Unlike Santaโs reindeer, this brand of magic doesnโt just dart out of the skyโฆ
GIANT SPRUCE IS COMINโ TO TOWN

In early November, a massive Norway spruce tree will leave Drysdaleโs Tree Farm in Egbert, Ontario. A long truck with trailer will haul the precious cargo southward down Highway 400, and eventually westward toward Halton Region, exiting at Trafalgar. The truck will meander through back roads of Downtown Oakville to its final destination, Towne Square. The Drysdale team, after securing the area for public safety, will use a large crane to hoist the one-ton tree onto a one-ton stand held in place by six discreetly camouflaged, one-ton concrete blocks.

Over the next several days, a magnificent transformation will occur. Once the evergreenโs branches have been eased down by gravity and fluffed back into their original, glorious state, Drysdaleโs tree experts will string up 25,000 lights, carefully wrapping them around individual branches.
At last, the panache! Darlene Janeiro Design, assisted by Oakville Hydro, will bring to life their โSymphony of the Starsโ vision by adorning the tree with musical instruments, stars, as well as bows and baubles galore in blue, white and gold.
MAIN EVENT

At 5:00 pm on Friday, November 20th, Downtown Oakville becomes a winter wonderland. The eveningโs festivities include roaming carollers, all-ages dance lessons, and live entertainment on George Street by classic-contemporary jazz vocal trio The Ault Sisters and their band.
Guests can dine in the areaโs beloved restaurants, while merchants extend their hours for holiday shoppers and gift buyers. Outside, pedestrians are invited to enjoy a cup of hot cocoa from a vintage Airstream trailer, with Santa himself presiding over a picture-perfect evening.
As the big โlight upโ moment approaches, crowds will gather around Towne Square (no need to jostle; thereโs no bad view when the tree is 45 feet high!). All are encouraged to join the loud countdown to 5:30 sharp, when the tree will light up the night and fill Downtown Oakville with cheer.
Itโs time to spread the word and mark calendars. No one should miss this opportunity to bask in communal holiday vibes at Downtown Oakvilleโs premier yuletide event.


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