Your Guide to the City’s Must-See Entertainment.
March 27, 2026 | Community members will gather in Oakville for an inspiring night of entertainment and philanthropy at the Bloom with Hope Gala. Hosted by the Lighthouse for Grieving Children & Families, the event takes place on March 27, 2026, from 6:00 pm to...
July 1, 2026 | Canada Day along the waterfront is always a memorable experience, and the Town of Oakville offers one of the region’s most picturesque celebrations. On July 1, 2026, residents and visitors are invited to gather at Bronte Heritage Waterfront Park from 5:00...
April 15, 22, 23, 25, and 26, 2026 | The Just for Laughs Road Tour 2026 is set to turn April into a month of unstoppable laughter across Ontario. As an extension of the world-renowned Just for Laughs brand, this touring showcase brings together a...
June 21, 2026 | The inaugural Bronte Harbour Classic 5K Race is set to take place on Sunday, June 21, 2026, offering runners and families a unique Father’s Day experience at Bronte Harbour Park in Oakville, Ontario. Hosted by the Bronte Runners Club, this professionally...
August 3, 2026 | The annual Art in the Park festival returns to Bronte Heritage Waterfront Park on Monday, August 3, 2026, from 10:00 AM to 5:00 PM, offering a vibrant day of artistic exploration, live entertainment, and community engagement. Situated at the scenic corner of Bronte...
January 29 - December 17, 2026 | Oakville Galleries’ Little Artists programme invites families to explore art and creativity together through monthly workshops that blend hands‑on art‑making with literary elements from the Oakville Public Library. Designed to engage young minds alongside their caregivers, Little Artists...
January 8-9, 11, 17, 23 and May 24, 2026 | Ballet Jörgen, Canada’s fifth-largest ballet company, is poised to unveil a spellbinding new production: a Canadian-inspired adaptation of Shakespeare’s A Midsummer Night’s Dream, set to Mendelssohn’s lyrical music and infused with the magic of the...
November 1, 2025 – May 3, 2026 | The Oakville Symphony proudly unveils its 2025–2026 season—a rich, diverse program designed to inspire, delight, and unite the community through the transformative power of music. Under the dynamic leadership of Music Director Lorenzo Guggenheim, the upcoming season...
October 4 - March 21, 2026 | The Oakville Chamber Orchestra (OCO) has joyously announced its highly anticipated 2025–2026 season, promising both musical familiarity and festive delight for audiences across Oakville, Burlington, and Mississauga. Now in its 35th season, the OCO continues to fulfil its...
October 3, 2025 - May 9, 2026 | The Classic Albums Live Series is a concert series that features performances of iconic albums by well-known artists. The series is known for its dedication to reproducing classic albums with a high degree of accuracy, aiming to...
