Events happening in Oakville.

Saturday, September 19th

OCA Trunk Sale and Food Drive - Potential Vendors Register Now Part 2

The OCA Trunk Sale and Food Drive invites attendees to shop for items while supporting a local food drive. Proceed from sales benefit those in need in the community.

Holiday Inn Oakville (Centre) by IHG

Saturday, September 19th

9:00AM – 2:00PM

REmarket Oakville

REmarket Oakville is Oakville's first reuse and recycling market, taking place September 19, 2026 at Bronte Heritage Waterfront Park. Inspired by the long-running St. Lawrence Market REmarket, this free, community-driven event invites residents to recycle hard-to-dispose items, participate in a FreeMarket (give and take items), and connect with local environmental organizations.

Bronte Heritage Waterfront Park

Saturday, September 19th

10:00AM

Adult Book Club:Beneath the Surface

This month's discussion focuses on Beneath the Surface: Poems & Stories by Chief Stacey LaForme. Copies are available on a first-come, first-served basis at the Woodside branch; quantities are limited. Attendees are invited to drop in and share their thoughts at the monthly meet-up. No registration is required. The book club welcomes people of all backgrounds and abilities. Discussions remain focused on the books themselves. Participants are asked to follow the library's Customer Code of Conduct and review the Programming FAQ for guidelines and frequently asked questions.

Woodside Branch

Saturday, September 19th

10:00AM – 2:00PM

Trafalgar-Chartwell Block Party 2026

The Trafalgar-Chartwell Block Party 2026 is a free, family-friendly community event on Saturday, September 19, 2026, from 10:00 a.m. to 2:00 p.m. The event brings residents together to strengthen neighbourhood connections and learn about local programs, services, and volunteer opportunities. Activities include inflatable games, face painting, balloon art, outdoor family activities, food trucks, guided tours of the community centre, and a visit from Oakville Fire Services. Residents can engage with local organizations, discover available programs and services, and explore ways to volunteer and get involved in neighbourhood activities. Open to all residents — newcomers and long-time community members alike.

Reynolds Street Park

Saturday, September 19th

11:00AM – 7:00PM

Asian Heritage Festival 2026

The Halton Asian Heritage Society is hosting a free community celebration at Fowley Park. Attendees can enjoy live performances, food trucks, vendors, games, and cultural booths. The event welcomes families and neighbours of all ages.

Fowley Park

Saturday, September 19th

7:00PM – 10:00PM

Banff Centre Mountain Film Festival

The Banff Centre Mountain Film and Book Festival is one of the world's largest and most prestigious mountain festivals. Each fall, the festival is held in Banff, Alberta. Following the main festival, the Banff Centre Mountain Film Festival World Tour travels to over 600 communities across more than 40 countries. The World Tour showcases award-winners and audience favourites selected from over 400 entries submitted to the Festival competition each year. Films explore remote landscapes, environmental issues, and action sports, offering audiences close encounters with the mountain world. The 2025/2026 World Tour presents a collection of outdoor storytelling and filmmaking from around the globe.

Oakville Centre — AEG Liebherr Auditorium

Sunday, September 20th

Bake & Connect: Sourdough Bread-Making Workshop (and more!)

A hands-on sourdough workshop where participants bake, sample premium olive oil, enjoy coffee and snacks, and connect with fellow attendees. Sept. 20, Oakville.

Taste of Colombia - Fair Trade Coffee & Gift Shop

Sunday, September 20th

9:00AM – 3:00PM

2026 motionball Marathon of Sport

Marathon of Sport Oakville 🏃 is a day of friendly competition, teamwork, and inclusion in support of Special Olympics Canada Foundation. Teams are paired with one or two local Special Olympics athletes to compete together in activities including soccer, basketball, benchball, and more. Participants receive a motionball Under Armour T-shirt and hat, light breakfast, lunch, and refreshments throughout the day, a personal fundraising link with incentive prizes, and a drink at the official after-party. Registration is open. Organizers invite teams to set fundraising goals and prepare for a day alongside Special Olympics athletes.

Appleby College

Sunday, September 20th

9:00AM – 6:00PM

British Car Day 2026

British Car Day is hosted annually by the Toronto Triumph Club on the third Sunday of September. Since its inaugural event in 1984, the gathering has grown to draw more than 1,000 British cars and over 9,000 spectators, making it the largest one-day, all-British car event in North America. Car owners and visitors travel from Ontario, the northeast United States, the Maritime provinces, Quebec, and Manitoba to attend.

Bronte Creek Provincial Park

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

Sunday, September 20th

11:00AM – 4:00PM

The 6th Annual Braden Story Invitational ⛳️

The 6th Annual Braden Story Invitational 🏌️‍♂️ honors a good friend while bringing golfers together. First tee off is at 11:00 AM. Attendees should arrive 30 minutes before their allotted tee time to ensure a smooth flow.

Deerfield Golf Club · $112.62 CAD

Sunday, September 20th

11:00AM – 4:00PM

3rd Annual Oakville Women Expo

The 3rd Annual Oakville Women's Expo 🌸 celebrates women in business with shopping, networking, and community connection. Attendees can discover unique products from local entrepreneurs, meet business owners, connect with community organizations, and support women-owned businesses. Sunday, September 20, 2026, 11:00 AM – 4:00 PM at Hilton Garden Inn Oakville, 2774 South Sheridan Way. Admission is open to the public. The event welcomes shoppers, those seeking to network, people looking for local services, and anyone interested in a community day out with friends and family. RSVP at www.oakvillemarket.info

Hilton Garden Inn Oakville

Tuesday, September 22nd

7:00PM – 9:00PM

Summer Reading: Author Talk with Wiley Wei-Chiun Ho - Fall Salon Evening

An Evening with Wiley Wei-Chiun Ho 📚 Wiley Wei-Chiun Ho, author of The Astronaut Children of Dunbar Street, will discuss her debut memoir at Summer & Grace Gallery. The book follows her family's immigration from Taiwan to Canada in 1979, and the difficult decision her parents made to return overseas for work, leaving twelve-year-old Wiley and her siblings to grow up independently in Vancouver. It is a close, personal story about distance, family, and what gets passed down across generations and borders. Wiley has published short stories and essays in PRISM international, Ricepaper Magazine, River Teeth, and Room, and was a finalist for the 2021 Jim Wong-Chu Award for Emerging Writers. She lives in North Vancouver. Open to individuals and book clubs. Light refreshments will be served. Books will be available for purchase and signing.

· $19.56 CAD

Thursday, September 24th

10:00AM – 11:00AM

Bronte Book Club

This month's book club will discuss Remarkably Bright Creatures by Shelby Van Pelt. Copies are available to borrow at the Woodside Branch on a first-come, first-served basis; quantities are limited. The book club session takes place at Taste of Colombia Café, 67 Bronte Road. Parking: free parking is available behind the café at all times. Street parking is paid. If parked behind the café, use the back entrance. Registration is required. To cancel your spot, log into MyEvents using your library card (or use the reference number from your confirmation email if you registered another way), call your local branch, or email oplreference@oakville.ca. Have ready the program title, program date, and names of registered individuals. For more information, see the Program FAQ.

Community Location

Thursday, September 24th

4:00PM – 5:00PM

Little Artist

Oakville Galleries and the Oakville Public Library are partnering to offer a mini art class paired with a story and literary connection. Held at the Education Centre at Oakville Galleries, the program invites young artists to explore and create a variety of new projects each week through hands-on art-making activities.

Oakville Galleries

Thursday, September 24th

5:00PM – 9:00PM

16th Annual LiONS LAIR Gala

The 16th Annual LiONS LAIR is an annual celebration of entrepreneurship.

Oakville Conference & Banquet Centre · $282.50 – $2260 CAD

Thursday, September 24th

6:00PM – 11:59PM

The PARTY: Dinner in Gairloch Gardens

For the first time since 2019, guests are invited to Gairloch Gardens for an evening under the stars. Set beneath a tent overlooking Lake Ontario, The PARTY: Dinner in Gairloch Gardens brings together art, exceptional dining, and the local community in support of Oakville Galleries. Proceeds support Oakville Galleries' free access to exhibitions and programs, education initiatives, and the artist-in-residence program. Guests may arrive via complimentary valet service courtesy of Mercedes-Benz Oakville. The evening includes dinner by Kerr Street Catering, wines, cocktails by Spring Mill Distillery, and dessert by Tatin Bakehouse. Live music accompanies the elegant lakeside setting throughout the night. A live auction features exclusive experiences and contemporary artworks. The event offers an opportunity to gather with collectors, patrons, and supporters of contemporary art.

Gairloch Gardens

Thu, Sep 24 – Sun, Sep 27

Mean Girls the Musical

Mean Girls The Musical brings the iconic hit film to the stage with sharp comedy, bold music, and all the high school drama of the original. When Cady Heron enters North Shore High for the first time, she discovers that surviving the social jungle of high school may be tougher than life on the African savanna — especially when she meets Regina George and The Plastics. The musical features book by Tina Fey, music by Jeff Richmond, and lyrics by Nell Benjamin. The show includes depictions of bullying, cyberbullying, mature language, sexual innuendo, and teen drinking, as well as Mean Girl commentary on body image. It is recommended for ages 13 and up.

Oakville Centre — AEG Liebherr Auditorium