Events happening in Oakville.

Friday, September 11th

6:30PM – 9:00PM

Taste & Paint: An Evening of Wine and Art Recurring Event

Taste & Paint: An Evening of Wine and Art is a Paint & Sip experience at Oakville Galleries. Guests will create their own acrylic artwork while enjoying premium Niagara wines and locally crafted charcuterie in an inspiring gallery setting. The evening features a tasting of two premium Niagara wines — a white and a red — led by Louise Wilson Cormier, Master of Wine, of Wilco Fine Beverage. As one of only nine Masters of Wine in Canada, Cormier will guide guests through each wine's distinctive character, origin, and flavour profile, and share insights into the Niagara wine region and the art of wine appreciation. Locally crafted charcuterie and light refreshments complement the wine pairings. Guests will leave with their finished painting and a deeper appreciation for Niagara wines. Ages 19+.

The Studio at Oakville Galleries in Gairloch Gardens · $95

Friday, September 11th

8:00PM

ORGANEK

Ørganek, one of Poland's most acclaimed alternative rock bands, will perform with Canadian soul and R&B artist Sean Jones as the opening act. Ørganek was founded in 2013 by singer, guitarist, songwriter, and composer Tomasz Organek in Toruń, Poland. The band is known for its energetic rock sound, thoughtful lyrics, and powerful live performances. The current lineup includes Tomasz Organek (vocals and guitar), Adam Staszewski (bass guitar), Robert Markiewicz (drums), and Tomasz Lewandowski (keyboards). The band gained widespread popularity with albums including Głupi, Czarna Madonna, and Ocali nas miłość, with best-known songs such as "Mississippi w ogniu," "Kate Moss," "Wiosna," and "Niemiłość." Ørganek has received numerous Fryderyk Awards and is highly regarded for its contribution to modern Polish rock music. Sean Jones, a Juno Award-winning Canadian singer, songwriter, and performer, is renowned for his soulful voice and captivating stage presence. He has shared the stage with Stevie Wonder, Beyoncé, Usher, and David Foster, and is celebrated for his Soul in the City concert series at Casa Loma. Early bird pricing is available until August 1, 2026.

Oakville Centre — AEG Liebherr Auditorium

Saturday, September 12th

6:30AM – 3:00PM

Bronte Classic

The 2026 Bronte Classic, hosted by the Halton Region Salmon & Trout Association, is the organization's flagship event of the year. The tournament has sold out in recent years and is capped at 51 boats, so spots are expected to fill quickly. The event draws both competitive teams pursuing prize money and recreational anglers. Entry registration is now open.

Bronte Harbour

Sat, Sep 12 – Sun, Sep 13

Warsztaty Cichych Ustawień Systemowych

Bert Hellinger's Systemic Constellations Workshop in Oakville, September 12–13, 2026, led by Karol Stępnia, a certified systemic constellations therapist, psychobiologist, physiotherapist, and Sivananda yoga teacher. This workshop is for anyone experiencing stagnation, health challenges, relationship difficulties, parenting concerns, family conflict, inheritance issues, financial blocks, or professional obstacles — or who feels fear, doubt, or resistance about moving forward in life. Participants work through their own constellations to gain new perspective on these areas. Schedule — Saturday, September 12, starting 9:00 AM: opening and meditation (9:00), pair exercises (9:30), individual constellations (10:00), lunch break (2:00 PM), meditation (3:30 PM), constellations (4:00 PM), breathwork and visualization session (6:00 PM), closing (7:00 PM). Sunday, September 13, starting 9:00 AM: opening and meditation (9:00), pair exercises (10:30), constellations (11:00), lunch break (2:00 PM), constellations (3:30 PM), breathwork and visualization (5:00 PM), closing (6:00 PM). Pricing: $490 for two-day individual constellation; $280 for one-day individual constellation; $210 for observer participation (no personal constellation). A $150 deposit is required to reserve a place. Spaces are limited. Bring a change of shoes or warm socks and a blanket — each day closes with deep meditation, breathwork, and visualization. Lunch breaks are approximately one hour. Private constellations are also available Friday, September 11, 9:00 AM–4:00 PM (limited spots). A free information session for interested participants is held Friday, September 11 at 7:00 PM. Location: Neutral Living Wellness Center, 1312 Speers Road, Oakville. To register or for more information, call (905) 616-2010 or email info@birdsnestcenter.com. ❤️

Oakville, Ontario

Saturday, September 12th

12:00PM – 3:00PM

Art in My Garden

Art in My Garden is a free outdoor art exhibit showcasing 65+ local artists across 35 beautiful gardens in Old Oakville, along Lake Ontario. Visitors can stroll through the picturesque neighbourhood, meet the artists, and celebrate creativity immersed in art and nature. Attendees are invited to participate in the Hanging in Harmony project, creating their own artwork to be displayed at Erchless Estate on the event day. Pre-event painting activities are available at Knox Church on August 22nd, 23rd, 29th, and 30th. This is the 6th year of Art in My Garden, which has welcomed over 1,500 visitors in previous years.

Around participating gardens in Old Oakville.

Saturday, September 12th

12:00PM – 3:00PM

Art In my Garden Sept. 6, 2025 walk around to find me

Art in My Garden is an outside walk-about tour featuring 70+ artists. The tour takes place in downtown Oakville by the lake.

St Andrew's Roman Catholic Church Oakville

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

Tuesday, September 15th

7:00PM

Adult Book Club

This month's book club will discuss *First Lie Wins* by Ashley Elston. Copies are available on a first-come, first-served basis at the Glen Abbey branch; quantities are limited. Drop in with no registration required. Participants will develop critical thinking, collaboration, social skills, and communication through group discussion. The Oakville Public Library welcomes people of all backgrounds and abilities. Discussions should remain focused on the book itself. All attendees are expected to follow the library's Customer Code of Conduct, which prohibits hateful or targeting language. For full guidelines and frequently asked questions, see the Programming FAQ.

Glen Abbey Branch

Wednesday, September 16th

Paint a Patagonia Volcano with Watercolour Brush Pens at Staples Store 4

Participants will create a colourful volcano landscape inspired by Patagonia's mountains while learning beginner-friendly watercolour techniques. This hands-on session covers foundational skills including wet-on-wet painting, layering, and colour blending — all applied to a scenic mountain composition.

Staples Oakville

Wednesday, September 16th

Paint a Patagonia Volcano with Watercolour Brush Pens at Staples Store 78

Participants will create a colourful volcano landscape inspired by Patagonia's mountains while learning beginner-friendly watercolour techniques. This hands-on session covers foundational skills including wet-on-wet painting, layering, and colour blending — all applied to a scenic mountain composition.

Staples

Wednesday, September 16th

CrowdPicks Film Fest: Oakville 2026 PRE-SALE

Oakville based film festival that platforms young and emerging filmmakers!

Cineplex Cinemas Oakville and VIP

Wednesday, September 16th

7:00PM – 8:00PM

Cookbook Club

Explore and discuss food culture from around the world. Each session will focus on a specific theme centered on food. Participants can read a fiction or non-fiction book from a curated list. Feel free to try out recipe or two and discuss your experiences in this interactive new book club This month's theme is ________. Registration is required. Please review the guidelines and frequently asked questions on our Program FAQ Skills Learned: Social Skills, Communication Need to cancel? Please let us know. If you have to cancel your spot for any reason, you can do so by: 1. Logging into MyEvents using your library card. If you did not register with your library card, you will need the reference number you received in your confirmation email. 2. Phone your local branch , or email oplreference@oakville.ca. Please have ready the program title, program date, and names of registered individuals. Access to facilities and programs may be impacted by evolving health and safety protocols related to COVID-19. The town will follow all requirements and recommendations issued by Halton Public Health and any applicable provincial regulations. The Town may use discretion to impose its own requirements. You will be notified if your registration is impacted by any changes.

Iroquois Ridge Branch

Thursday, September 17th

7:00PM – 8:00PM

In Conversation With Liane Moriarty

Big Ticket, In Conversation From the #1 New York Times bestselling author of Big Little Lies , the runaway phenomenon that inspired the megahit HBO series. In this highly anticipated sequel, Liane Moriarty examines the complexities of modern women’s lives, shining light on family dynamics and long-hidden truths with wit and compassion. Whether you’ve read Big Little Lies or not, this is the perfect novel for longtime fans and new readers alike. The last time we saw the women of Big Little Lies —Madeline, Celeste, Jane, Renata, and Bonnie—their children were five years old. If someone wasn’t invited to a birthday party, feelings were hurt. But ten years have passed and the kids are in high school, navigating all of the drama that accompanies teendom (goodbye playdates, hello drugs, sex, and alcohol). When the high school principal receives a threatening package in the mail, word quickly spreads throughout the community and parents are in an uproar. But Madeline, Celeste, Jane, Renata, and Bonnie have other things to worry about. Celeste’s mother-in-law, Mary Louise, is behaving oddly—is it old-age forgetfulness and bluntness or something more sinister? Madeline is facing perhaps the biggest challenge of her life, Jane is at a dangerous fork in her marriage, Bonnie has realized there’s only so much solace in yoga. And Renata? Renata is living her best life—revenge is sweet. When a stranger begins lurking around the school asking supposedly innocent questions, this tightly connected group of women must finally face the full repercussions of the big little truths they have and haven’t shared with their kids. Because the stakes are now much higher than not being invited to an ice-skating party—and the ice has never been thinner for any of them.

Oakville Centre — AEG Liebherr Auditorium

Fri, Sep 18 – Sun, Sep 20

Oak Fall Market & Food Festival

Oak Fall Market & Food Festival features food vendors, craft stalls, and activities throughout the day.

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.

Fri, Sep 18 – Fri, Oct 16

Introduction to Painting with Wayne Moore

This introductory painting course builds foundation skills in rendering subjects with paint. The curriculum covers understanding value, the properties of paint, colour mixing and methods of application, and developing form and volume through line, tone, texture, and colour. Students will choose their own subject matter and complete a value painting and a limited colour painting. For the first class, bring any acrylic painting supplies you already have. All supplies and tools will be discussed in the opening session. Also bring a colour photograph and a black and white copy of the same subject matter you may be interested in painting, along with a small sketchbook and an HB pencil.

Joshua Farm Gallery

Fri, Sep 18 – Sun, Sep 20

God of Carnage

Back by popular demand, God of Carnage is a play by Yasmina Reza, translated by Christopher Hampton and directed by Yo Mustafa. Originally written in French as Le Dieu du carnage and first published in 2008, the play follows two sets of parents who meet to discuss a playground incident in which one couple's son has hurt the other couple's son. What begins as a civilized conversation gradually devolves into chaos as the parents become increasingly childish and their composure unravels.

Oakville Centre — Studio Theatre - Lower Level