2026 Oak Park Fall Fair: A Celebration of Community and Tradition
September 12, 2026 | 11:00 am – 10:00 pm
Oak Park Neighbourhood Centre, 2200 Sawgrass Drive, Windfield Parkette
The Oak Park Fall Fair, a beloved community event in Oakville, returns on September 12, 2026, with a day filled with festivities, fun, and family-friendly activities. Held annually, the Fall Fair is a cherished tradition that brings together residents of all ages to celebrate the vibrant spirit of Oak Park and its surrounding neighbourhoods. This year’s fair promises to be bigger and better than ever, with a lineup of events and attractions that showcase the best of what the community has to offer, including entertainers, tons of family-friendly activities, inflatables, an outdoor movie, a silent auction, a bake sale, and more.
The Oak Park Fall Fair is not just about entertainment; it’s also about fostering a sense of community. The event serves as a gathering place for neighbours to connect, share experiences, and celebrate the diverse and welcoming environment that Oak Park is known for. Local organizations and charities will also be present, offering information about their services and providing opportunities for fairgoers to get involved in community initiatives.
For families, the fair offers a wealth of activities that will keep children entertained and engaged. The Kids’ Zone will feature face painting, a petting zoo, and interactive games, while the main stage will host a series of performances geared towards younger audiences. The fair’s focus on inclusivity and accessibility ensures that all members of the community can participate and enjoy the day’s festivities.
The fair is set to be a memorable event that captures the essence of the community’s spirit and traditions. With its wide range of activities, entertainment, and opportunities for connection, the fair is an event that residents look forward to year after year. Whether you’re a longtime resident or a newcomer to the area, the Oak Park Fall Fair is the perfect way to celebrate the start of the fall season and experience the warmth and camaraderie that make Oak Park such a special place to live.
Don’t miss out on this year’s Oak Park Fall Fair on September 12th—mark your calendars, gather your loved ones, and prepare for a day of fun and festivities you won’t soon forget!

