Oakville, Ontario History: 9 Key Moments That Shaped the Town

Oakville is one of Burlington's closest neighbours, and its story starts at a harbour. The history of Oakville, Ontario runs from thousands of years of Indigenous presence to a founding family, a busy port, and a lakefront that welcomed people travelling the Underground Railroad. This Oakville history timeline walks through 9 key moments that shaped the town, then shows where you can still see that history today.

Early Oakville History: Indigenous Roots and the Founding of the Harbour

1. Long Before 1827: Indigenous Peoples and the Land at Sixteen Mile Creek

Indigenous peoples lived along this shoreline and the creek valleys long before the town was planned. Today, Tannery Park honours that history with a First Nations history wall that depicts a timeline of First Nations settlements in the area, and the Oakville Museum explores Indigenous history alongside the town's later stories.

2. 1827: Colonel William Chisholm Buys 960 Acres

In 1827, Colonel William Chisholm (1788 to 1842) purchased 960 acres of land from the Crown at the mouth of Sixteen Mile Creek and planned out the Town of Oakville and its harbour. Chisholm was an enterprising merchant and shipbuilder, and he is considered Oakville's founder.

3. 1828: The Harbour Is Completed

Chisholm completed work on Oakville's harbour in 1828, giving the new town the port it needed to ship goods and build vessels. The harbour remains the heart of Downtown Oakville today.

4. 1834: Oakville Becomes a Port of Entry, and Bronte Is Established

In 1834, Oakville was declared a Port of Entry into Canada, with William Chisholm serving as customs inspector. That same year, a small fishing settlement was established at the mouth of Twelve Mile Creek, which became Bronte Village. Bronte is now one of Ontario's oldest communities and is still known for its marine heritage.

How Oakville Grew: Post Offices, Lighthouses, and the Chisholm Family

5. 1835: Oakville's First Post Office Opens

Oakville's first post office was built in 1835, and William Chisholm served as the first postmaster. The building still stands today as the Old Post Office.

6. 1837 to 1960: The Old Oakville Lighthouse

The first Oakville lighthouse was built in 1837 to mark the mouth of Sixteen Mile Creek, but a severe storm destroyed it in 1886. The current lighthouse was built in 1889 and served as a navigational aid until 1960. It can be explored near the Oakville Yacht Squadron, a short walk from downtown.

7. 1856: The Custom House and Erchless Estate

Chisholm's son, Robert Kerr Chisholm, built the Custom House in 1856 as an office for the customs service. It was later converted into the Chisholm family home now known as Erchless Estate, which overlooks the harbour and Sixteen Mile Creek. Six generations of the Chisholm family lived at Erchless, and the estate is now home to the Oakville Museum.

Oakville's Black History and the Road to a Museum

8. The Underground Railroad and Oakville's Black History

Oakville's lakefront was an entry point for many people travelling the Underground Railroad. The Oakville Museum tells those stories in two permanent exhibits, "Freedom, Opportunity and Family: Oakville's Black History" and "The Underground Railroad: Next Stop Freedom."

9. 1952: The Old Post Office Becomes Oakville's First Museum

In 1952, through the efforts of William Chisholm's great-granddaughter, Hazel Chisholm Hart Mathews, the Old Post Office was moved to Lakeside Park, where it became Oakville's first museum. Her work helped set the stage for the heritage sites that Oakville preserves today.

Where to Experience Oakville's History Today

Most of Oakville's best heritage sites are within walking distance of Downtown Oakville.

• Oakville Museum at Erchless Estate (8 Navy Street): tour the Chisholm family home, the Custom House exhibits, and the permanent Black history exhibits.

• Old Post Office at Lakeside Park: Oakville's first post office and first museum.

• Old Oakville Lighthouse: a short walk from downtown near the Oakville Yacht Squadron.

• Downtown Oakville's heritage homes: many are marked with plaques naming the original owner, which makes for an easy self-guided walk.

• Bronte Village and Sovereign House: explore the historic harbour village and the heritage house where local artists show their work weekly from late May to the end of October.

• Tannery Park's First Nations history wall: a timeline of First Nations settlements in the area.

Pair a walk through heritage Downtown Oakville with a picnic at the waterfront. Our guide to the best picnic spots in Oakville has ideas, and the Oakville Museum's hours and programs are listed on the Town of Oakville's website.

Oakville History FAQ

Who Founded Oakville, Ontario?

Colonel William Chisholm founded Oakville. In 1827, he purchased 960 acres from the Crown at the mouth of Sixteen Mile Creek and planned out the town and its harbour.

When Was Oakville Founded?

Oakville was planned in 1827, its harbour was completed in 1828, and it was declared a Port of Entry in 1834.

What Is Erchless Estate?

Erchless Estate is the former home of Oakville's founding family, the Chisholms, and is now the Oakville Museum. It sits at 8 Navy Street, overlooking the harbour and Sixteen Mile Creek.

How Old Is the Oakville Lighthouse?

The current lighthouse dates to 1889. The original, built in 1837, was destroyed by a storm in 1886, and the lighthouse served as a navigational aid until 1960.

Is Bronte Part of Oakville?

Yes. Bronte Village was established in 1834 as a fishing settlement at the mouth of Twelve Mile Creek and is now one of Oakville's distinctive waterfront neighbourhoods.

Explore More of Oakville

There is a lot more to see in this lakeside town. Browse more Oakville stories on Burlington 365, and follow along for local history, events, and things to do across Burlington and its neighbours.