The Downtown Oakville Jazz Festival is an annual summer jazz festival that has taken place every year since 1992.
Past headliners at the Waterfront Festival included Jann Arden, Oakville resident Tom Cochrane, Great Big Sea, Alannah Myles, Blue Rodeo, Susan Aglukark, Michelle Wright, Jacksoul, Colin James, The Philosopher Kings, Jesse Cook, Finger Eleven, Justin Hines, Bedouin Soundclash, Ill Scarlett, Jully Black, David Usher, and Hedley.