Learn about Oakville’s Historical Past in this Two-Day Itinerary

The Town of Oakville is located on the Treaty Lands and Territory of the Mississaugas of the Credit. With a rich and celebrated history, Oakville has many landmarks and historical buildings that commemorate our diverse history. From being an entry point for many American slaves travelling the Underground Railroad in search of freedom to being a major point of entry for sailors and merchants in the 19th century, Oakville is the ideal location for anyone interested in learning more about Canadian history. This two-day itinerary will take you on a tour of some of Oakville’s must visit historical landmarks and buildings.

Day 1:

Tour Oakville’s Historical Buildings and Memorials

Start your day by exploring the historical buildings in Downtown Oakville. Lakeside Park is home to Erchless Estate, The Coach House, The Thomas House, and The Old Post Office. Built in 1858, Erchless Estate was home to six generations of the Chisholm family for over 130 years including William Chisholm who founded Oakville in 1827.

The Town of Oakville purchased the home in 1977, and it has been open to the public since 1991. It is now the home of the Oakville Museum. Visit the Museum and explore the many exhibits such as Pathway to the Stars: A Centennial Celebration of Oakville’s Contributions to the Royal Canadian Air Force and Freedom, Opportunity and Family: Oakville’s Black History exhibits.

After you have explored the Oakville Museum and surrounding grounds, which have been restored to replicate the original gardens based on photographs taken in the early 1900’s, visit the Oakville Historical Society located in the cottage on the North side of the Erchless Estate grounds. If you are traveling in a group of six to fifteen people you can book a walking tour with the Oakville Historical Society. The Oakville Historical Society currently offers tours of four key locations in Oakville. Visit here to see which tours are offered and to book your tour. Tours must be booked at least two weeks in advance.

Prefer to go at your own pace? There are eleven QR code decals located in Downtown Oakville. Scan a QR code and watch a short video about the historic building or landmark you are near. Visit here for more information.

After your tour of the historical landmarks in Downtown Oakville make your way to the Native Art Gallery in Towne Square. This Art Gallery opened in 1995 and is dedicated to displaying artwork created by Canadian Indigenous artists.  

After you have spent your morning in Downtown Oakville it is time to explore Kerr Village. Start by getting lunch at the Oak Café Gallery. This quaint café not only serves up delicious coffee, sandwiches, and waffles they also display art created by local artists on their walls. Enjoy your lunch while looking at the artwork displayed throughout the café.   

Your next stop after lunch is Tannery Park. Along the way stop at Turner Chapel Antiques and Appraisers. This antique store was originally an African Methodist Episcopalian Church established in 1890. In 2002, Jed Gardner purchased the building and while preserving the structure of the original building he opened Turner Chapel Antiques. The origins of the Church was referenced in the documentary Finding Freedom on the Sixteen which premiered in Oakville at Film.ca in 2024.

After you have explored the antique store continue your adventure to Tannery Park. Tannery Park is a beautiful park with superb views of Lake Ontario and Sixteen Mile Creek. Tannery Park is home to the Rooted in the Land history wall which was created in consultation with the Mississaugas of the Credit First Nations and a Moccasin Identifier installation. Both installations teach about the history of the First Nations, Métis, and Indigenous communities in Oakville and the surrounding areas.

After you have explored Tannery Park head back to Downtown Oakville and visit the Veteran’s Wall memorial at George Square. The Memorial recognizes the brave and heroic Oakville residents who served their country in the First and Second World Wars.

After you have visited the Memorial wall, it is time for dinner.

Visit The King’s Arms in Downtown Oakville. The King’s Arms is said to be the first pub established in Oakville. Originally named the Duke of Bedford, the pub was built in the mid 1970’s. The building which now hosts The King’s Arms was shown in the 1863 Town Plans as the property of Captain William Wilson. Along with The King’s Arms delicious food, they also won Visit Oakville’s Talk of the Town award for best cocktails. Enjoy a cocktail with your dinner or order off their craft beer menu where you will find a wide range of Ontario made beer including local beer made at Oakville’s own Cameron’s Brewing.

Wrap up your evening by watching a performance at the Oakville Centre for the Performing Arts. The Performing Art Centre opened in 1977 and its main theatre sits just under 500 people. Upcoming performances include Fearless by the Oakville Symphony, Vibrant also by the Oakville Symphony, and All the World’s a Stage by the Oakville Wind Orchestra. For a full list of all the upcoming performances, please visit here.

Day 2:

Discover Bronte Village’s Diverse History

Spend your second morning in Oakville in Bronte Village learning about Oakville’s fishing industry and exploring the Moccasin identifier trail.

Bronte was founded in 1834 and was known for exporting wheat, building ships, and it’s thriving commercial fishery and stonehooking industry. In Bronte Heritage Waterfront Park you will find the Fisherman’s Memorial honouring the fishermen who battled the elements to earn a living. In the 1900’s over half of the adult men in Bronte made their living out on the water year-round.

Throughout the Bronte Heritage Waterfront Park, you will also see painted Muskoka chairs. All the Muskoka chairs were painted by residents, local artists and business owners. New chairs are added each year and remain in the park year-round.

Next, take a self-guided tour of the Moccasin Trail alongside Bronte Creek. Throughout the trail you will see thirteen plaques containing Indigenous stories relating to the land, water and sky. This trail starts at the Bronte Marsh and concludes at the Bronte Creek information hut on Rebecca Road and Mississauga Street.

After your tour, it’s time for lunch at Marine Tavern in Bronte. Marine Tavern is a historical building built using stones and Dundas shale from Lake Ontario through the stonehooking process.

After lunch, visit the Howard Iron Works Printing Museum. This museum is home to a variety of different printing presses and specialty equipment dating from the 1830’s to 1950’s. Book a tour with the museum and learn more about the history of printing in Canada. Admission is free to the museum, but they do require that you make advance reservations.   

After you have toured the Printing Museum, visit the It Belongs in a Museum! How and why Museums Collect and Preserve exhibit at the Queen Elizabeth Park Community and Cultural Centre. This exhibit is dedicated to taking you behind the “artifact storage” sign and explains how and why museums acquire and care for their collections.

End your evening in Oakville with dinner at Ce Soir Brasserie and Bar. This French style restaurant was originally the home of a police station in the 1950’s. They have converted what was once a cell room into a wine cellar where one can host parties and intimate events. The exposed brick inside the restaurant is from the original building.

We hope that you have enjoyed visiting some of Oakville’s historical landmarks and were able to learn more about Oakville’s historical past.

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