Check out this listing from Deborah Cooper at Royal Lepage on Allan Street:

Oakville’s Culture Days festival starts this Thursday, September 19, and runs through October 12 with over 150 free events celebrating arts, culture, and community. As an official Festival Hub again this year, the town will host workshops, exhibitions, performances, and hands-on activities at venues across Oakville.

A major highlight is Faces of Culture, a portrait project open to all ages. You can also catch dance shows at OCPA, heritage events at Lions Valley Park, and ongoing programs at local libraries. Oakville was ranked the top mid-size city for Culture Days in 2024, and this year’s festival is shaping up to be just as impressive.

Oakville will mark the National Day for Truth and Reconciliation on September 30 with events that honour Indigenous communities and the children lost to residential schools. All month long, you can visit the Debwewin Truth Project at the Oakville Museum or catch a free concert with Indigenous artists and Sultans of String on September 26 at QEPCCC.

On September 30, Mimi O’Bonsawin will perform at the OCPA at 8pm, with drumming and activities starting at 6:30pm in Centennial Square. You can also walk the Moccasin Trails, visit Tannery Park’s Indigenous history wall, or explore book picks at the Oakville Library. Town Hall will raise the orange flag and light up orange to mark the day.

Downtown Oakville’s Towne Square is getting a $4.3 million upgrade starting January 2026, with a new water feature, oak-shaped benches, added trees, and improved accessibility. The redesign aims to make the space more inviting for events and daily use—and that’s just part of the plan. More features are coming, including updates to the lionhead fountain and the return of the historic clock.

Oakville’s Ryan Sharpe, 22, made his debut on Jeopardy! this past Monday, September 15, showing off his trivia skills on the iconic quiz show. A graduate of Abbey Park High School, Sharpe has been a longtime fan of the show and called it “such an institution.”

He’s no stranger to competition, having placed third in the 2018 Canadian Geographic Challenge and also appearing on the British quiz show University Challenge, which aired the same day. His Jeopardy! episode is now available to stream on Crave.

Lions Pool went to the dogs on Sunday, September 14, as the Oakville and Milton Humane Society hosted its popular annual Doggie Dip. The sold-out event saw dozens of pups of all sizes take turns swimming in 30-minute slots, with smaller dogs diving in first, followed by the big breeds later in the morning.

The event not only gave local dogs a chance to cool off and have fun, but also helped raise funds for the Humane Society’s community programs. With safety top of mind, dogs wore lifejackets and owners stayed poolside to supervise. It was a joyful day of splashes and wagging tails, all for a great cause.

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Wednesday, September 17
☀️ Mostly sunny, nice
High: 23°C | Low: 15°C

Thursday, September 18
☀️ Mostly sunny, very warm
High: 26°C | Low: 15°C

Friday, September 19
🌤️ Mostly sunny, pleasant
High: 22°C | Low: 12°C