Oakville is a prosperous lakeside town on the western shore of Lake Ontario, about 30 km southwest of Toronto. It has a handsome harbour area and a well-preserved historic downtown, and is large enough (population around 210,000) to have a distinct character of its own, separate from the sprawl of the Greater Toronto suburbs nearby.
The town was founded in 1827 as a planned commercial port by William Chisholm, who needed a harbour for shipping grain and timber out of Upper Canada. That origin is still visible in the tight grid of Old Oakville, where Georgian commercial buildings and Victorian houses cluster around Oakville Harbour. The Oakville Museum at Erchless Estate — the Chisholm family home — is the best place to understand how the town came to be.
Modern Oakville is wealthy: one of the higher median incomes of any municipality in Canada, a function of its proximity to Toronto and its concentration of corporate head offices along the QEW corridor. That wealth is most visible in the Old Oakville restaurant strip, where Hexagon holds a Michelin star and the independent shops lean toward the luxury end. The counterpoint is Kerr Village, a more diverse, affordable strip a few blocks west that has considerably more local character.
Outside the downtown, the big draw is the natural landscape. Sixteen Mile Creek runs through a wooded ravine that cuts right across the town, and the trail system along it is excellent. Glen Abbey Golf Course — a Jack Nicklaus design that hosted the Canadian Open for decades — sits along the creek valley and has the Canadian Golf Hall of Fame on its grounds. West of town, Bronte Creek Provincial Park offers camping and swimming within reach of the city.
The GO train from Toronto's Union Station runs to Oakville in about 35 minutes, making it an easy day trip from the city or a quieter base if you want to avoid downtown Toronto prices.