Together With

Good morning Oakville. Happy Wednesday!

Before we get started, we have some new things to share.

  1. Monthly Event Guides 🗓️

Many of you took the time to fill out our year-end feedback survey (thank you), and we heard you loud and clear on one specific issue: events further out in advance. To give you time to plan ahead, and to make sure nothing is sold out, we are going to start releasing monthly event guides.

These guides will include all of the most anticipated events for the month ahead, with more detailed descriptions and pricing information. The guide, however, will not include every single event happening. You should continue to reference the newsletter for the smaller, day-to-day events, plus ones that might not have been posted yet.

All the events in the guide will also be included in the normal newsletters as their date approaches. You can expect our February Guide to land in your inbox tomorrow!

  1. We’re trying out a new section ✒️

We are trying out a new “History” section where we do short write ups on the history of Oakville. We will keep these write ups short and interesting, with cool stuff you probably did not know.

This idea is still being ironed out. The section will appear on slower news days instead of “News” or “Community”, and today’s newsletter includes the very first one about how Oakville was named.

We included a poll after the section to hear your feedback and help us decide if this new section is here to stay, please let us know your thoughts - we would really appreciate it.

Ok, without any further ado, here is what to expect in today’s issue:

  • 🛍️ Toronto Premium Outlets plans expansion, and record-breaking snow

  • ⚓️ Why Oakville Is Called Oakville?

  • 📅 Some exciting events to keep you busy!

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

~ Nick

Together with Making Waves Swim School

It all starts here 💦 

Swimming is one of the most important life skills a child can learn, and starting early sets the foundation for confidence, awareness, and lifelong safety in and around the water. At Making Waves Swim School, every swimmer’s journey begins with safety-first instruction that builds comfort and trust before advancing skills.

Our programs are designed to grow with your swimmer, starting with essential water safety fundamentals and progressing through skill development, endurance, and technique. Experienced coaches guide swimmers at every stage, reinforcing safe habits while encouraging confidence and independence.

📌 Parent & Tot (2–30 months)
📌 Little Waves (2–5 years old)
📌 Big Waves (6+ years)

With warm pools, small class sizes, and a structured curriculum, swimmers receive the consistency and support they need to thrive from their very first lesson onward.

We’re Oakville’s largest newsletter with over 14,000 readers.
Let’s work together.

🛍️ Toronto Premium Outlets Plans Big Expansion

Toronto Premium Outlets in Halton Hills is eyeing a major upgrade, proposing a 116,000-square-foot expansion that would add 25 new retail units and a four-storey parking garage. If approved, this would boost the mall’s total retail space by 14.5 per cent and increase its parking capacity to 3,551 spaces. Town staff are currently reviewing the site plan, which was officially submitted in May 2025.

There’s no word yet on which stores might move into the new units, but the outlets remain a go-to destination for shoppers across Halton, including many from Oakville, looking for deals on brand-name items. The proposal suggests construction could begin in late 2026 if approvals go smoothly.

❄️ Toronto Buried in Record Snowfall

Sunday dumped a historic 46 cm of snow at Pearson Airport, officially making it the snowiest day Toronto’s ever seen since records began in 1937. Add some lake-effect magic and certain downtown spots ended up under more than half a metre of powder, all thanks to a rare combo of arctic chill and tropical moisture. The storm hit so hard, it even outdid the previous 1966 record by nearly 10 cm.

And yes, Oakville got snow too. Shovels were working overtime from Bronte to Joshua Creek, and at this point, the piles surrounding the driveway are so high there's nowhere left to toss any more snow.

⚓️ Why Oakville Is Called Oakville?

357 Trafalgar road in 1958. The house has likely the largest, and possibly the oldest, white oak tree in the original village of Oakville. Photo from oakvillehistory.org

At first glance, the name Oakville sounds almost painfully literal. Trees. Oaks. A village. Done.

But the real reason Oakville is called Oakville has far less to do with scenery and far more to do with trade, industry, and one of the most valuable resources in early Canada.

Oak was money

In the early 1800s, the land around present-day Oakville was covered in massive old-growth white oak forests. These were not decorative trees. White oak was essential for making barrel staves, the curved wooden slats used to build barrels.

And barrels were how almost everything moved in the 19th century. Food, alcohol, dry goods, military supplies. If you controlled oak staves, you controlled trade.

A working port, not a quiet village

Before Oakville had streets or neighbourhoods, Sixteen Mile Creek was already busy. Trees were cut inland, shaped by hand, floated down the creek, and stacked along the shoreline. From there, oak staves were loaded onto schooners and shipped across Lake Ontario.

In the 1820s, William Chisholm, a merchant, shipowner, and veteran of the War of 1812, recognized the commercial potential of this location. He purchased land at the mouth of Sixteen Mile Creek and deliberately planned a harbour and settlement around it.

He was not naming a picturesque lakeside town. He was building a working port centred on oak.

The name Oakville was practical. It described what the town produced.

A name that stuck

The oak trade eventually faded. Timber exports declined, wheat took over, and Oakville slowly shifted away from its industrial roots. But the name remained.

Today, Oakville is known for its waterfront, neighbourhoods, and quality of life. Yet the name still carries a reminder of what this place was built on.

Oakville was not named for beauty. It was named because oak was valuable, and this was one of the best places to move it to market.

Historical source: Oakville and the Sixteen, Hazel C. Mathews.

Wednesday, January 28
☁️ Cloudy
High: -11°C | Low: -15°C

Thursday, January 29
☀️ Sunny
High: -12°C | Low: -23°C

Friday, January 30
⛅ Mix of sun and clouds
High: -14°C | Low: -17°C

Oakville Digest is 100% free to read, independently owned, and locally operated (written by me).

Your contributions go directly towards keeping this newsletter going so we can have more fun and build more community.

Thank you for your support!
~ Nick

🖼️ Inhale. Exhale. – Art Exhibition Opening
Thu 1/29 @ 5:30PM-8:30PM
SavvyArt Market

Vision Board Workshop
Wed 1/28 @ 6PM
Figaro Coffee House

🥌 Women’s Winter Classic Bonspiel
Thu 1/29 @ 9AM
Oakville Curling Club

Coffee & Conversation
Thu 1/29 @ 1PM-2PM
1515 Rebecca Street

🎨 Little Artist – Kids Art Class
Thu 1/29 @ 4PM-5PM
Oakville Galleries

🎬 OFFA Pop-Up Shorts – Student Film Showcase
Thu 1/29 @ 5:30PM-7:30PM
Staples Oakville Studio

💘 40+ Singles Mixer
Thu 1/29 @ 7PM
Figaro Coffee

🎸 Duende – Nuevo Flamenco Live
Fri 1/30 @ 8PM
Oakville Centre for the Performing Arts

🎻 Candlelight Concert – Queen vs. ABBA
Fri 1/30 @ 6:30PM
Knox Presbyterian Church

🍝 Pasta Making Class – Chef Enzo
Fri 1/30 @ 6:30PM-9PM
Mercato Sociale

🎤 Stompin’ Tom Turns 90 – Whiskey Jack & Séan Cullen
Fri 1/30 @ 8:30PM
Moonshine Tavern

🎻 Candlelight Concert – Tribute to Adele
Fri 1/30 @ 8:45PM
Knox Presbyterian Church

🧘 Free Intro to Pilates
Sat 1/31 @ 10AM-11AM
300 North Service Rd W

🎉 Stretch Health Oakville Open House
Sat 1/31 @ 1PM-4PM
Greenlight Personal Training

🧘 Breathwork & Sound Bath
Sat 1/31 @ 10:30AM-12:30PM
Divinity Wellness

👨‍👩‍👧 Family Paint Party
Sat 1/31 @ 4PM-6PM
Monaghan’s Sports Pub & Grill

🧘 Yoga Swing Sound Bath
Sat 1/31 @ 7PM-8:30PM
Haven Pilates & Co.

🎤 Masoud Sadeghloo – Persian Pop Concert
Sat 1/31 @ 8PM-11PM
2700 Bristol Cir, Mississauga

❓ Trivia

Thank You!

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NICK POLLOCK
Founder / The Oakville Digest
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