Events happening in Oakville.

Saturday, August 22nd

⚾ Lead Off Youth Home Run Derby (11U-14U) | Oakville

⚾ 25 Sluggers. 9 Medals. 1 Ring. Spots are limited—don’t miss out!

Palermo Park

Saturday, August 22nd

10:00AM – 4:00PM

Youth Home Run Derby

Lead Off Youth Home Run Derby invites young hitters to step up to the plate and compete in a single-elimination home run competition. Two divisions accommodate different age groups and skill levels: a 200-foot fence for 12U–14U and power-hitting 11U players, and a 125-foot fence for 8U–10U players. All players are welcome, whether from house league or rep teams. Competition format: Round 1 features 10 swings per player, with a minimum of 15 advancing after hitting at least one home run. Round 2 narrows the field to the top 10 with another 10 swings. The Championship Round crowns the winner through a 10-out format, with a 5-swing tie-breaker if needed. Awards include a custom championship ring for first place, silver and bronze medals for second and third place, and finalist medals for 7th–10th place finishers. Registration begins at 9:00 AM, with first pitch at 10:00 AM. Early bird pricing is available until July 2, after which rates increase. Spots are limited.

Palermo Way, Oakville, ON L6M, Canada

Friday, August 28th

6:30PM

Bronte's Dominican Bachata Party 2026

Bachata Nights 💃 at Bronte Market Square A free, 13-week summer celebration for all ages featuring live music and dancing. Tiana Adames leads the event, bringing rhythm and community spirit to the heart of Bronte. Every Friday, June 19 – September 11, 6:30 PM – 9:30 PM at Bronte Market Square.

Bronte Market Square – 2445 Lakeshore Rd W

Saturday, August 29th

10:00AM – 2:00PM

Put your Paws up

Meet the groomer and trainer. Get a professional photo with your best friend, and enjoy treats from Tailblazers.

Saturday, August 29th

3:00PM – 10:00PM

CRAFT Live-Afro Caribbean Canadian Waterfront Fete

This celebration honours the vast contributions and influences of African, Caribbean, and Black Canadians in shaping the community, culture, and economy. The event features live music spanning Soca, Calypso, Reggae, Steelpan, R&B, Afro Beats, Disco, Jazz, Blues, and Funk & Soul, plus a live DJ and vendors. Free and open to all ages.

Bronte Heritage Waterfront Park

Friday, September 11th

3:45PM – 11:00PM

10TH ANNUAL KERRFEST

Kerrfest 🎉 celebrates its 10th anniversary with a two-day street party and outdoor music festival featuring Canadian artists, local food vendors, an artisan market, and family-friendly activities. The event runs September 11–13, 2026, at Westwood Park in Oakville, Ontario, and is presented by the Kerr Village BIA.

Westwood Park · $11.98 – $267.58 CAD

Sunday, September 13th

12:00AM – 12:00AM

Doggie Dip Fest

Doggie Dip Fest 🐕 is a celebration of summer, dogs, and community. Dogs and their humans are invited to splash, play, shop, and enjoy a day filled with connection and fun. The event features a dog pool party, interactive vendor experiences, and plenty of opportunities to explore — a way to wrap up the summer season with your four-legged friend.

Lion's Pool

Sunday, September 13th

10:00AM

Doggie Dip Fest -- Oakville

Doggie Dip Fest 🐶 returns this September for an end-of-summer celebration. Dogs can enjoy 30-minute swim sessions, visit the Barkin' Market (a collaboration with Toronto Dog Moms), meet other dogs, and participate in photo opportunities and vendor activities. Swim sessions are limited and fill up quickly. Registration is $30 per dog and includes one 30-minute swim session. Festival access is open to the public; attendees can visit the Barkin' Market to shop without registering a dog. All proceeds from swim session registrations and Barkin' Market attendance support food, shelter, medical care, and adoption services for animals in need. Lions Pool, Oakville. Sunday, September 13. Register at hsomh.ca/doggiedip.

Lions Pool · $30

Fri, Sep 18 – Sun, Sep 20

Oakville Harvest Vendor Festival & Artisan Showcase

Oakville Harvest features fresh vendors and local crafts in a relaxed, welcoming atmosphere.

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

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

Saturday, September 26th

10:00AM – 4:00PM

Harvest Festival

Experience harvest season as it might have been over 100 years ago at Bronte Creek Provincial Park's historic Spruce Lane Farm. The Friends of Bronte Creek Park are hosting two days of demonstrations and activities. Activities include picking your own pumpkins (by donation), touring the 124-year-old farmhouse, watching apple cider pressing demonstrations, and making a souvenir using a 4-foot-long cross-cut saw. Tractor-drawn wagon rides tour the park, and heritage demonstrations run throughout the event. Seasonal refreshments and food are available for purchase.

Bronte Creek Provincial Park

Saturday, September 26th

10:00AM – 4:00PM

Print Expo & Fair 2026

The Print Expo & Fair is a community event for all ages featuring tours, demonstrations, hands-on printing activities, and workshops. Attendees can explore and purchase work from artists, printers, and book arts enthusiasts. The venue is fully accessible.

Howard Iron Works Printing Museum

Sunday, October 4th

10:00AM – 1:00PM

Labpalooza 2026: Dog Walk and Play

Lab-rescue fundraiser 🐕 near Parking Lot A, featuring pet caricatures, professional photography, dog massage, pup cups, a nutrition centre, games, and a guided dog walk through the park trails. All dog breeds are welcome.

Bronte Creek Provincial Park

Thursday, October 15th

8:00PM – 10:00PM

Sing Pitch Perfect with Deke Sharon & Splush

Sing Pitch Perfect with Deke Sharon & Splüsh 🎤 Deke Sharon, Music Director for the three Pitch Perfect films, will lead attendees in learning and singing "Since U Been Gone" entirely a cappella. Sheet music will be provided for all participants. Splüsh, the SING! Canadian A Cappella 2025 double champions, will perform. Deke will also share behind-the-scenes stories from the movie-making process. Open to all ages and singing levels — non-singers are welcome.

Oakville Centre — AEG Liebherr Auditorium

Sunday, October 18th

10:00AM

Wiggle Waggle Walk 2026

Wiggle Waggle Walk 🐾 The Humane Society of Oakville, Milton & Halton invites the community to participate in the Wiggle Waggle Walk on Sunday, October 18, 2026, at River Oaks Community Centre in Oakville. Participants can walk, run, bike, stroll, or simply join for a day of fun. Proceeds support the organization's work reuniting lost pets with their families, operating the Pet Food Bank, providing humane education and youth programs, and caring for vulnerable animals. Participants are welcome to walk in honour of a beloved pet, in memory of a companion, or simply to support animal welfare. Registration is available at hsomh.ca/wigglewaggle.

River Oaks Community Centre, Room A

Sunday, October 25th

1:00PM

The Velveteen Rabbit

Big Ticket, Family: A Musical Adaptation by Mya Leworthy, Naomi Jijina, and Lucy Ellis. On Christmas Eve, a young boy waits eagerly to discover whether he has received a toy rocket that flies like the real thing. When his grandmother catches him snooping through presents, she offers him a deal: he can stay up later if he listens to her story about a toy called the Velveteen Rabbit.

Oakville Centre — AEG Liebherr Auditorium

Saturday, December 5th

1:00PM

Lady Next Door

Two neighbours share a common courtyard — Huguette, exuberant and free-spirited, and Vana, orderly and organized. Their clashing lifestyles create constant friction: Huguette hangs laundry to loud music, sets up a tent for backyard camping, and practices acrobatic bike tricks, while Vana is most bothered by Huguette's perpetually overflowing garbage cans. Through the chaos, the neighbours gradually learn to communicate and understand each other better. A glimmer of friendship emerges as they discover they may not be so different after all. This female clown duo delivers physical comedy and heart — expect to laugh until you cry.

Oakville Centre — AEG Liebherr Auditorium