December 6, 2021

Oakville is rich in historic locations and artistic experiences, making it the perfect destination for those looking to dive into local culture. 

Follow along with our two-day itinerary to experience a vacation perfect for history buffs and art enthusiasts alike. 

Note: This itinerary is based on information available in early November 2023. Please contact businesses directly to confirm details.

Day 1: Historic eats, holiday tours and theatrical showcases

Museum Christmas Tour

Start your day with a hot drink and tasty treat from Taste of Colombia in Bronte Village. This café is a mainstay in the neighbourhood, offering authentic Colombian coffee. 

Enjoy your hot drink while walking alongside Lake Ontario and exploring the At Home in Bronte: Winter Edition Muskoka chair display. There are 100 Muskoka chairs painted by Oakville artists scattered throughout the neighbourhood. You can also learn more about Oakville’s fishing history by visiting the Fisherman’s Memorial in Bronte Heritage Waterfront Park. 

Next head to Downtown Oakville, step back in time and learn more about the history of Oakville at the Oakville Museum. Visit the two current exhibits:

  • Freedom, Opportunity, and Family: Oakville’s Black History
  • The Underground Railroad: next Stop, Freedom

Or visit during one of their winter themed events.

Make the quick walk into the heart of Downtown Oakville for dinner at Ce Soir. This building dates back to the 1800s when it housed Anderson Bank. It then transitioned into a local police station in the 1950s.

Wrap up your evening by taking in a live show at the Oakville Centre for the Performing Arts. This local theatre has an incredible lineup through the winter months, including the Oakville Symphony’s Family Holiday Concert, Elvis: A Christmas Special and BurlOak Theatre Groups’ Rapunzel a Holiday Pantomime.

Day 2: Gallery sights, waterfront walks, and create your own art

Cove bronte

Fuel up with breakfast from your hotel or grab a quick bite at Vereda Central Cafe before making your way to Tannery Park. Discover the First Nations history wall depicting a timeline of First Nations settlements in the area and the First Nations Moccasin Identifier gathering circle.

Next, grab lunch at The King’s Arms. In the mid-1970s The King’s Arms was the first pub to be established in Oakville, under the name “The Duke of Bedford. The building which houses The King’s Arms is shown in the 1863 Plan of the Town of Oakville as the property of Captain William Wilson, whose family members were among the first settlers in Oakville. The foundations, basement, and some of the old house still form part of The King’s Arms to this day.  Although there have been many changes over the years, the character and atmosphere of a British Pub has remained.

After your lunch head over to the Oakville Galleries. There are two locations in Oakville. One is in Centennial Square and the other is located in Gairloch Gardens. The Centennial location is presenting the Leisure (Meredith and Carruthers and Susannah Wesley) Having Ideas by handling Materials exhibit and the Gairloch Gardens location is presenting the Elif Saydam Eviction Notice exhibit.

After being inspired at the Oakville galleries head to Pottery and Paint Cafe to create your own piece of art. Bring home a souvenir with their canvas painting experience. Reservations are not needed but are recommended.

Share your experiences with us by tagging @VisitOakville in all of your Oakville adventures.

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