Good morning Oakville. Happy Wednesday!

Here is what to expect in today’s issue:

  • 🗳️ Oakville elects Jeff Knoll to be new Mayor, trick-or-treating for tots on Kerr, and Grammy-nominated Laila Biali returns to Oakville

  • 🎃 Orsett Street has the spookiest house in town, children’s book from local publisher a finalist for a national award

  • 🗓️ Some exciting events to keep you busy!

Thanks for being part of our growing community, let’s dive in!

~ Nick

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Jeff Knoll Is Oakville’s New Mayor 🗳️

Town of Oakville

The results of Monday’s election are in, and Oakville has officially chosen Jeff Knoll to serve as the town’s new mayor. Having represented Ward 5 as a Town Councillor since 2000, Knoll was one of the longest tenured members of council, and he believes this level of experience is what made him so appealing to voters. “What I offered this community is change without a learning curve” he told the Oakville News. 

During his victory speech Knoll highlighted some of the actions he will prioritize as mayor, which include seeking to cancel the Minister’s Zoning Orders imposed by the Province to facilitate the controversial midtown development plan; establishing a lobbyist registry and citizen advisory committees; and keeping Oakville safe.

As the founder of Oakville’s local independent movie theatre and the Chair of both the Halton Police Services Board and the Oakville Public Library, Knoll has already established a strong presence within the community, and now he’ll have the chance to further lead and shape the future of Oakville as Mayor.

Little Tots Trick-Or-Treating On Kerr Street 👻

The businesses of Kerr Village are participating in a special event designed for little ones to enjoy all of the treats and none of the tricks of Halloween. On Friday, October 30th the annual “Little Tots Trick Or Treat” will take place between 11am and 2pm, providing a chance for younger children to dress up in their costumes and collect some candy without worrying about scary things like the dark, or doorbells they’re too small to reach. 

Around 18 local businesses will take part in the event, easily identified by the official ghost graphics that will be on display in their windows. Expect a fun afternoon of strolling through the shops and filling up a treat bucket with your tiny witch/black cat/Spiderman without having to worry about bedtime!

Grammy Nominee & Former Oakville Resident Laila Biali Comes To The Oakville Centre 🎶

Laila Biali, credit Chris Nicholls

When accomplished Canadian jazz singer and pianist Laila Biali plays at The Oakville Centre on Friday, October 30th it won’t be just another stop on tour for the 2026 Best Traditional Pop Vocal Album Grammy Nominee, but something more like a homecoming. 

Before moving to New York, Laila lived in Oakville for several years, and she still speaks warmly and vividly of her time here, remembering the colours that canopy Sixteen Mile Creek in the fall and the strolls her family used to take along the waterfront and around the harbour. She even rates her old favourite pizza from Il Fornello up there with anything that can be found in New York City! 

Laila’s upcoming performance is titled “Joni Mitchell & the Canadian Songbook Reimagined”, and will feature her signature jazz-pop interpretations of Joni classics as well as her take on songs from other Canadian legends like Neil Young and Sarah McLachlan. The show is a testament to all the talent this country has produced, both past and present, and a tribute to a musical tradition we should all take pride in. Oakville is certainly proud to celebrate Laila’s place in that tradition and to welcome her back to the place she once called home!

Spooky Things Are Happening On Orsett Street 🎃

The Oakville Digest

Right in the middle of an otherwise perfectly pleasant and classically suburban Oakville neighbourhood a house of horrors has popped up, as it does every October, much to the frightful delight of neighbours near and far. This is “Orsett After Dark”, the elaborate Halloween experience that has become an annual tradition on Orsett Street. 

“Enter if you dare” reads the archway that leads to a yard full of horror-inspired mannequins and animatronics that are both impressively creative and genuinely creepy. Think zombies, spiders, clowns, and anything else known to inspire phobias. The spooky scene is also haunted by a spirit of generosity, as visitors to the free walk-through are encouraged to leave donations that will go to the Sick Kids Foundation.

(Not for young children or the faint of heart.)

Book From Oakville Publisher Shortlisted For National Award 💖

Akemi’s Song, the moving children’s book written by Joanne Kwok, illustrated by Yiting Hui, and published by Oakville’s own Plumleaf Press, was a finalist for the Richard Allen Chase Memorial Award from the Canadian Children’s Book Centre. The award honours outstanding works of children’s literature that deal with big themes like kindness, inclusivity, and our relationship with the planet.

Akemi’s Song certainly fits those criteria. Kwok describes her picture book as “my love letter to Taiwan’s breathtaking natural landscapes and vibrant wildlife”, a backdrop she uses to tell the story of one flamecrest bird discovering herself and finding her song. Illustrated with care and detail, the book is already loved by readers, and its place on the shortlist for such a prestigious award was well earned!

🌹 Royal Canadian Legion Poppy Sales
Tue-Tue 10/27-11/10
Oakville Place

👻 Boos & Brews
Tue-Wed 10/27-10/28 @ 7:15PM
Downtown Oakville

📚 Bronte Book Club
Thu 10/29 @ 10AM-11AM
Taste of Colombia Café, 67 Bronte Road

🍳 Cooking Class at Paradiso
Thu 10/29 @ 6:30PM
Paradiso Oakville

🎨 Adult Drawing and Painting Course
Thu 10/29 @ 6:30PM-8:30PM
Oakville Galleries in Gairloch Gardens

👻 Haunted Happenings: Candlelight Tour
Thu 10/29, Fri 10/30 @ 7PM
Oakville Museum

🎬 Rocky Horror Picture Show 2026
Fri-Sun 10/30-11/1
Film.Ca Cinemas

🎃 Little Tot Trick or Treating
Fri 10/30 @ 11AM-2PM
Participating Stores in Kerr Village

🕯️ Candlelight: A Haunted Evening of Halloween Classics
Fri 10/30 @ 6:30PM
Knox Presbyterian Church

🎹 Laila Biali: Joni Mitchell & the Canadian Songbook Reimagined
Fri 10/30 @ 8PM-10PM
Oakville Centre for the Performing Arts

🎃 Tiny Tots 2026
Sat 10/31 @ 10AM-12PM
Downtown Oakville

🎃 Tails & Treats
Sat 10/31 @ 1PM
Downtown Oakville

🏒 U17 World Challenge
Sun-Sat 11/1-11/7
Sixteen Mile Sports Complex

🪔 Oakville Swasthyam Diwali
Sun 11/1 @ 12PM-9PM
Volodymyr Cultural Centre

🎃 Pumpkin Parade
Sun 11/1 @ 5PM-7PM
Oakville Museum

Wednesday, October 28
⛅ A mix of sun and cloud
High: 16°C | Low: 7°C

Thursday, October 29
🌦️ Chance of showers
High: 19°C | Low: 7°C

Friday, October 30
☀️ Sunny
High: 16°C | Low: 3°C

WEDNESDAY
8PM · Moonshine Cafe · Shjaane Glover

THURSDAY
1PM · Moonshine Cafe · Open Ukulele Session
8PM · Moonshine Cafe · Timber Trio

FRIDAY
8PM · BLK Swan · Mike and Marco
8PM · Lionheart Pub · Gordon DeSoza Band
8PM · The Gingerman · Caribou Band
8PM · Moonshine Cafe · Accidental Paradise

SATURDAY
2:30PM · Moonshine Cafe · Mike Branton & Friends
6PM · The Pipes and Taps Pub · Halloween Live
8PM · Moonshine Cafe · The Weber Brothers
8PM · Easy on Fourth · Live Music Saturdays
8PM · Lionheart Pub · Time Machine
8PM · The Gingerman · Fiddlestix Halloween Dance
8:30PM · The Oakville Pump & Patio · Radio Sonics: Halloween Bash

SUNDAY
2:30PM · Bronte Legion · Live Music on the Patio

  • Wednesday Night at BLK Swan Kitchen Hub

  • Wednesday at Kelsey's Burloak

  • Wednesday at Lionheart British Pub

  • Wednesday at The Oakville Pump

  • Thursday at The Bronte Legion, 79 Jones St

Thanks for reading the Oakville Digest today. If you know someone who’d like to visit a haunted house before Halloween, please share this with them!

~ Nick

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