Old Oakville, Oakville

The town began here: William Chisholm purchased the land at the mouth of Sixteen Mile Creek and developed the harbour and the settlement around it. Erchless Estate at 8 Navy Street, the family home, overlooks the harbour and stayed in the family for six generations; the Town bought it in 1976 and it has housed the Oakville Museum since 1983. The property includes an 1858 Italianate house, an 1856 Customs House and an 1835 brick store, and the Old Oakville Heritage Conservation District, designated in 1981, was the town's first and among the earliest in Ontario.

Housing runs from nineteenth-century homes, many predating 1860 on either side of Trafalgar Road, through late-Victorian and early-twentieth-century houses north of the commercial core, to later infill and low-rise condominium buildings. Streets follow a traditional grid close to the lake, and the heritage district extends south of Robinson Street to the lakefront between Sixteen Mile Creek and Allan Street.

Oakville Harbour sits at the creek mouth, with Lakeside and Dingle parks nearby, and the Sixteen Mile Creek valley adds green space along the western side. Towne Square on Lakeshore Road East provides a small public gathering space within the commercial core.

Lakeshore Road East is the main commercial street, with retail, restaurants and civic uses in storefronts that are often nineteenth-century buildings carrying heritage designation. Trafalgar Road connects the downtown north toward the QEW, and Oakville GO station on the Lakeshore West line lies north of the area.