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6 ways to experience Downtown Oakville's rich history and charm

Updated: Jun 13, 2021





Just east of Toronto sits Downtown Oakville, a growing city with a 'small town' feel. Once a Port of Entry, Oakville's harbour proved to be the drawing factor in William Chisholm's decision to purchase a spectacular amount of land in this vicinity. Although the pier is no longer used for commercial purposes, Oakville has seen the development of a variety of businesses from that first initial seedling.


From big-name retailers to family-owned shops and restaurants in Downtown Oakville, our town truly has it all. Join us as we explore the top 5 things to do in Downtown Oakville's rich history and charm like never before.


1. Experience history

Don't miss the opportunity to experience the historic Erchless Estate. Once home to Oakville's founding family, the buildings are now the setting for Oakville's community museum. Colonel William Chisholm, an enterprising merchant, and shipbuilder founded the town and built Erchless overlooking his new harbour and Lake Ontario.

Today, visitors can still enjoy the view and explore the beautiful buildings, grounds, and gardens of Erchless. The Oakville Museum normally offers guided tours of the Chisholm family home, changing exhibitions, special events, and programs that tell the fascinating stories of our town. Due to current COVID-19 restrictions, the Oakville Museum is currently closed to in-person visits but is open for virtual tours.


2. Escape Lakeside

Colonel William Chisholm's great dream of building a privately owned harbour for Upper Canada was quickly realized in 1834, when Oakville was declared a Port of Entry into Canada. Today, visitors can explore the Oakville Harbour and travel through maintained trails and three different parks adjacent to Sixteen Mile Creek.


The Oakville Yacht Squadron (OYS) is also situated near Sixteen Mile Creek's west side. OYS offers a wide range of family-friendly activities such as sailing lessons and club cruises.


3. Indulge in retail therapy


Skip the shopping mall and enjoy a day exploring the extensive retail mix in Oakville's downtown core. Downtown Oakville is home to trendy stores like Mendocino, Lemonwood, and Burrows Too. Experience personal service and quality close to home while also supporting local retailers in your community.


4. Discover recreational trails and walkways


If you're in the mood for some exercise, you can stroll, bike, or roll through one of the many trails near the Downtown core. Check out Larry Cain trail, a signed dedicated stretch of property along the waterfront, commemorating the achievements and training site for one of Oakville's Olympians.

Breathe in the fresh lakeside air while enjoying a self-guided Navy Street tour, courtesy of the Oakville Historical Society. You'll also find some great local park options, like Dingle Park or Lakeside Park.


With its blend of history, heritage, and modern development, it's no surprise that Oakville was ranked Canada's Best Place to Live in 2018. As the town continues to grow, there's something for everyone to experience and enjoy, especially Downtown.


5. Satisfy your hunger


Downtown Oakville is brimming with options to safely share drinks, food, and conversation. As summer rolls in, take advantage of the many patios and outdoor dining areas along Lakeshore, where you can relax, sip, nibble and people-watch. Besides a range of restaurants, Downtown Oakville also offers specialty bakeries and coffee shops to satisfy your cravings.


6. Discover recreational trails and walkways


If you're in the mood for some exercise, you can stroll, bike, or roll through one of the many trails near the Downtown core. Check out Larry Cain trail, a signed dedicated stretch of property along the waterfront, commemorating the achievements and training site for one of Oakville's Olympians.

Breathe in the fresh lakeside air while enjoying a self-guided Navy Street tour, courtesy of the Oakville Historical Society. You'll also find some great local park options, like Dingle Park or Lakeside Park.


With its blend of history, heritage, and modern development, it's no surprise that Oakville was ranked Canada's Best Place to Live in 2018 and as this little town continues to grow, there's something for everyone to experience and enjoy, especially Downtown.





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