
Together With

Good morning Oakville. Happy Friday! What is everyone doing this weekend? Anyone going to Acorn Fest? Let us know!
Here is what to expect in today’s issue:
🏢 New business in Oakville, art installation, and Poutine
🏃 Terry Fox run recap
📅 Some fun plans for your weekend!
Want to be featured on the Oakville Digest? Submit an event or news story!
Thanks for being part of our growing community, let’s dive in!
~ Nick
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🛌 The Sleeper Opens at Erchless
A haunting new art installation has opened at the Oakville Museum, created by acclaimed artist Shary Boyle for Ontario Culture Days. “The Sleeper,” now on display through November, invites visitors to slip written fears into a life-sized cardboard figure resting in the master bedroom of Erchless Estate. In spring, a Moon Garden will bloom where the sculpture is buried, symbolizing renewal from shared anxieties.
The installation is part of the Creatives in Residence series and ties into the Culture Days theme, “The Shape of Memory.” Locals can contribute answers to “What keeps you up at night?” at the museum or ballot boxes around town. On September 27, Erchless will also host a slate of free workshops from Shibori dyeing to Indigenous beading, turning the grounds into a hands-on celebration of Oakville’s stories.
🏢 Caldwell Securities Expands in Oakville
Caldwell Securities has officially opened a new office at Maple Grove and Cornwall, marking a major step in its Oakville growth. The grand opening welcomed Mayor Rob Burton and MP Stephen Crawford, who joined in celebrating the firm’s expanding presence in the community.
Founded in 1980, Caldwell has served the GTA for decades and spent the last 12 years rooted in Oakville. The new space at 1540 Cornwall Road, Suite 200, offers local clients full access to investment advisory services, retirement planning, and high-net-worth strategies.
🍟 Vote Now for Oakville’s Best Poutine
Visit Oakville has added a delicious new category to its Talk of the Town Awards: best poutine in town. Locals can vote until September 21 by entering the name of their favourite restaurant online, whichever spot gets the most votes wins.
The winner and runners-up will be announced next week and featured in Visit Oakville’s newsletter. A special window decal will also be given to the top pick to show off their title.
📰 More News

🏃♂️ Big Turnout, Bigger Impact at Terry Fox Run

Nearly 2,000 Oakville residents gathered at Coronation Park on Sunday for the 2025 Terry Fox Run, raising over $200,000 for cancer research. Participants chose from 1km, 2km, 5km, or 10km routes, each receiving a race shirt marked with “Finish It” in honour of Terry’s enduring mission.
The annual run once again celebrated the legacy of one of Canada’s most beloved heroes. “He’s Canada’s hero,” said co-chair Nathalie de Caen. “When you say you’re doing something for Terry Fox, people are thrilled to help.”
🔑 On The Market
Check out this listing from Michael Phinney at Royal Lepage on Ennisclare Drive W:
Can you guess the price?
Click here for a reveal.

Friday, September 19
☀️ Some clouds early, then sunshine
High: 20°C | Low: 12°C
Saturday, September 20
🌤️ Breezy & sunny
High: 17°C | Low: 14°C
Sunday, September 21
⛅ Sunny to partly cloudy; chance of afternoon shower
High: 23°C | Low: 18°C

🌰 Acorn Fest
Fri-Sat 9/19-9/20
Towne Square
🍷 Paint & Sip – Golden Ginkgo
Fri 9/19 @ 7PM-10PM
Taste of Colombia
🕯️ Candlelight Tribute to Coldplay
Fri 9/19 @ 8:45PM
Knox Presbyterian Church
💃 Fiesta Fridays – Latin & Ballroom Dancing
Fri 9/19 @ 8:45PM-12AM
Boleo Dance Studio
🚶 Morning Walk & Coffee
Sat 9/20 @ 7:30AM
Oakville Water Works Park
📚 Adult Book Club – A Friend in the Dark
Sat 9/20 @ 10AM-11AM
Woodside Branch Library
🎨 Watercolour Workshop with Barry Coombs
Sat 9/20 @ 10AM-5PM
Joshua Farm Gallery
💃 Salsa Night – Live Latin Dance
Sat 9/20 @ 6PM
Taste of Colombia
🪔 Navli Navratri Cultural Celebration
Sat 9/20 @ 6:30PM-11:45PM
St. Volodymyr Cultural Centre
🎬 Banff Mountain Film Festival World Tour
Sat 9/20 @ 7PM
Oakville Centre for the Performing Arts
🎤 Speakeasy – Live Rock & Soul
Sat 9/20 @ 8:30PM
The Pipes and Taps Pub
🎶 From The Hip – Tragically Hip Tribute
Sat 9/20 @ 8:30PM-11PM
Oakville Pump & Patio
🎸 Rewind – Classic Rock Night
Sat 9/20 @ 9PM
Tin Cup Sports Grill
🏃 Sunday Run Club Fundraiser
Sun 9/21 @ 8AM-11AM
Coronation Park
🚗 British Car Day
Sun 9/21 @ 9AM-4PM
Bronte Creek Provincial Park
🍎 Bronte Farmer’s Market
Sun 9/21 @ 10AM-2PM
Bronte Market Square
🎶 A Night with Ella & Sarah – Dinner & Performance
Sun 9/21 @ 5PM
Oakville Conference & Banquet Centre
🧘 Prenatal Yoga
Sun 9/21 @ 5PM-6:15PM
2525 Old Bronte Rd Unit 105
☕ Coffee & Conversation – Women’s Centre
Mon 9/22 @ 10AM
The Women’s Centre
🧘 Release & Rise – Autumn Equinox Sound Bath
Mon 9/22 @ 7:30PM-8:45PM
Neutral Living Wellness Studio
🏋️ Pelvic Floor Core Restore
Tue 9/23 @ 10AM-10:45AM
2525 Old Bronte Rd Unit 105
👩🦳 My Wisdom Circle – Golden Girls 50+
Tue 9/23 @ 11AM
AXP House, Mississauga
🤝 LeadTribes Oakville Networking
Tue 9/23 @ 1PM
Touchdown Coworking Space
🤝 Oakville Networking Social
Tue 9/23 @ 5PM-8PM
Monaghan's Sports Bar & Grill
🧘 Free Gallery Flow Yoga Class
Tue 9/23 @ 5:30PM-6:30PM
Joshua Farm Gallery
🏃 Lululemon Lakeshore Run Club
Tue 9/23 @ 6:30PM
George’s Square
💘 Speed Dating – Ages 28–39 (Men Sold Out)
Tue 9/23 @ 7PM-9PM
Paradiso
🧘 Restore & Regulate Movement Group
Tue 9/23 @ 7PM-8:15PM
4125 Upper Middle Rd #101, Burlington
👶 Halton Baby-Friendly Initiative – 25th Anniversary
Wed 9/24 @ 10AM-1PM
1151 Bronte Rd
🍂 Seasons Changing – Fall Celebration
Wed 9/24 @ 5PM-6:30PM
Monarch House
💃 Dance Essentials Class
Tue 9/24 @ 6:30PM
Taste of Colombia
Thank You!
Thanks for reading the Oakville Digest today. If you found something useful, share it with someone who you want to have dinner with this weekend.
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