Eastlake is the gateway to Oakville and back in the 1830s Oakville was the gateway to freedom for many African Americans stowed away in grain vessels on ships destined for Oakville harbour. During this time Oakville was also a terminus for the Underground Railroad, and was a beacon of freedom for many African-Americans who fled to Canada. Legend has it that a tunnel ran from the Sixteen Mile Creek to the Herb Merry House on Trafalgar Road, and there is also some evidence to suggest there may have been a tunnel leading under Navy Street from near the Custom House. Many of these freed slaves would then head east to the City of Toronto where they would begin new lives as free men and women. Their story and journey to freedom is on display at the Oakville Museum located at 8 Navy Street.

In the early 1900s Oakville became known as a resort town for wealthy Torontonians looking to build country estates. Jeweller James Ryrie was the first of Toronto’s elite to build a grand estate called Edgemere, on Oakville’s prime waterfront. Edgemere, was known for its elaborate Japanese gardens. Herbert Cox’s estate called Ennisclare, included stables and polo grounds. Department store magnet Timothy Eaton was another early resident. His estate was called Ballymena. With all this opulence Lakeshore Road East became known as “Millionaires’ Row.” These estate homes with their expansive and valuable waterfront property would eventually give way to new home developments. Today, all that remains of these landmark estates are the stone pillars, cast iron gates, and stone walls that accent Lakeshore Road east.