Events happening in Oakville.

Your Oakville event calendar. What’s on this week: festivals, markets, live music, classes, and family days out.

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Sunday, September 20th

9:00AM – 12:00PM

Oakville Terry Fox Run 2026

The annual Terry Fox Run takes place at Coronation Park, honouring Terry's legacy and raising funds for cancer research. Participants are invited to bring friends, family, and community spirit to join together in support of the cause. Registration opens at 10:00 a.m., with the run beginning shortly after.

Coronation Park, Oakville

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Fri, Oct 2 – Sat, Oct 3

Acorn Fest 2026

Acorn Fest 2026 Location: Towne Square, 94 George St., Oakville Time: Friday, October 2 | 5:00 p.m.–10:00 p.m. & Saturday, October 3 | 12:00 p.m.–5:00 p.m. 🍂 Acorn Fest is back! Celebrate all things fall in Downtown Oakville with a movie night, live entertainment, local shopping, fall fun, eats and treats, and more! For more information, contact [email protected] .

Towne Square

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Saturday, September 19th

Oakville Civitan Farmer's Market

Dorval Crossing Civitan Farmer's Market opens May 2 and operates every Saturday from 8:00 a.m. to 1:30 p.m. through the end of November. The Town of Oakville's longest-running farmer's market, it features local vendors and growers. All proceeds from market stall rentals are donated to local Oakville charities.

Dorval Crossing East Plaza

Islamic Calligraphy Painting Worskhop | Naveen Khan Art

MOTW Coffee & Pastries · $75 CAD

Dog Days of Ontario Culture Days: Oakville 2026

Saturday, October 3rd

1:00PM – 5:00PM

Dog Days of Ontario Culture Days: Oakville 2026

Micah Lexier’s Dog Days of Ontario Culture Days is a multi-location experience exploring the ritual and culture of dogs and their humans. Dog Days of Ontario Culture Days consists of a pair of independent yet thematically linked components: Guess Your Dog’s Age or Weight: A performance in which a “carnival guesser” attempts to accurately guess a dog’s age or weight. In exchange for a donation to a local dog charity, dog owners will receive a custom-minted coin as a memento of having participated in the project. A Portrait of The Person Making a Portrait of Your Dog: A live drawing activation where visitors receive a free sketch of their dog by a local sketch artist, while a second artist sketches the first artist at work. Dog owners get to keep their sketch, while Micah Lexier keeps the second sketch, to be included in a subsequent publication. This edition of Dog Days of Ontario Culture Days is produced in partnership with the Town of Oakville. Please note: We oversell these events to make sure that the greatest number of people have an opportunity to attend. Any remaining space will be opened up to those who sign up and are present on site at the event. Pet Portraits are first come, first served. Tickets do not guarantee portraits. – Donations can be made at the event in support of The Farley Foundation, a charity that helps pets across Ontario receive essential veterinary care. -- This program is part of the Ontario Culture Days 2026 Creatives in Residence series, and is curated by Dave Dyment. – Dog Days of Ontario Culture Days is made possible thanks to Tourism Niagara-on-the-Lake, the City of Toronto, the Province of Ontario, the Tourism Partnership of Niagara, and the Ontario Arts Council. We acknowledge the support of the Canada Council for the Arts and producing partners Evergreen Brick Works, Town of Oakville, The Niagara Pumphouse Arts Centre, Temiskaming Art Gallery, Waterfront BIA and Arts Council Windsor & Region. This event is part of the Ontario Culture Days 2026 Oakville Festival Hub. To see all Oakville Hub events from September 18 - October 4, 2026, click here . Registration policy: To help make our events available to as many people as possible, we may accept more registrations than the event’s capacity. Admission is available on a first-come, first-served basis and cannot be guaranteed once capacity is reached. We recommend arriving at least 15 minutes before the event begins.

Oakville Museum · Free

Saturday, October 3rd

1:30PM – 4:00PM

Good to know

Oakville events — frequently asked questions

What events are happening in Oakville this weekend?

This page lists every upcoming event in Oakville, including this weekend. Use the When filter at the top of the calendar to jump to This week, or pick a custom date range to see exactly what's on Friday, Saturday and Sunday: concerts, markets, festivals, theatre and family activities. The calendar is updated daily, so new events appear as soon as they're announced.

What are the best things to do in Oakville?

There's something on year-round: waterfront festivals and live music in summer, farmers' markets, art exhibitions at Oakville Galleries, theatre, fitness and wellness classes, and family days out across downtown Oakville, Bronte and Kerr Village. Browse by category above to find the kind of thing you're in the mood for.

Are there free events in Oakville?

Yes, many Oakville events are free, including outdoor concerts, community markets, library programs and seasonal celebrations. Each listing shows pricing where the organizer has provided it, so the free events are easy to spot as you scroll the calendar.

What family-friendly things to do are there in Oakville?

Plenty. Oakville has family events all year: splash pads and park days in summer, holiday markets and skating in winter, plus story times, workshops and kids' festivals. Filter the calendar by category to see family-friendly events happening soon.

How do I add or submit an event in Oakville?

If you're hosting something in Oakville, use the Submit your event button at the top of the calendar. It's free. Once it's approved, your event appears on this calendar and can be featured in The Oakville Digest newsletter, which reaches thousands of local readers each week.

How often is the Oakville events calendar updated?

Daily. The Oakville Digest adds new concerts, markets, festivals and community events as soon as they're announced and drops them once they've passed, so this calendar stays current. Bookmark the page and check back through the week.

Events happening in Oakville.

Featured.

Oakville Terry Fox Run 2026

Acorn Fest 2026

Oakville Civitan Farmer's Market

Islamic Calligraphy Painting Worskhop | Naveen Khan Art

Dog Days of Ontario Culture Days: Oakville 2026

Shibori Indigo Dye Bandanas

Canadian Art Hop: In Conversation: Ali Cherri’s To Fall, Patiently

In Situ: A Guided Art and Landscape Tour

Adult Drawing and Painting Course

Museum Walking Tour: Oakville and the Underground Railroad

Winter Wonderland Paint and Sip

Islamic Calligraphy Painting Worskhop | Naveen Khan Art

Dog Days of Ontario Culture Days: Oakville 2026

Shibori Indigo Dye Bandanas

Canadian Art Hop: In Conversation: Ali Cherri’s To Fall, Patiently

In Situ: A Guided Art and Landscape Tour

Adult Drawing and Painting Course

Museum Walking Tour: Oakville and the Underground Railroad

Winter Wonderland Paint and Sip

The Sororum Presents: A Sunday Afternoon in Downtown Oakville

Gelli Plate Leaf Impressions

Fall Landscape Paint and Sip

Islamic Calligraphy Painting Worskhop | Naveen Khan Art

Dog Days of Ontario Culture Days: Oakville 2026

Shibori Indigo Dye Bandanas

Canadian Art Hop: In Conversation: Ali Cherri’s To Fall, Patiently

In Situ: A Guided Art and Landscape Tour

Adult Drawing and Painting Course

Museum Walking Tour: Oakville and the Underground Railroad

Winter Wonderland Paint and Sip

Ali Cherri: To Fall, Patiently

Culture Days 2026

World of Threads Festival 2026

Oakville events — frequently asked questions