Things to do in Oakville this September

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🎸 Kerrfest
Kerr Street's music festival turns 10 this year, with Colin James and the Jim Cuddy Band headlining at Westwood Park. Gates open 3:45PM Friday and 11:45AM Saturday.
🎟️ $12 - $30+
📅 Fri, Sep 11 – Sun, Sep 13
📍 Westwood Park

🎪 Oak Park Fall Fair
The 29th annual fair draws over 4,000 people for entertainers, inflatables, an outdoor movie, a silent auction and a bake sale. It has won Oakville's Platinum Readers' Choice for Best Festival.
🎟️ Free
📅 Sat, Sep 12 | 11AM–10PM
📍 Oak Park Neighbourhood Centre

🥟 Asian Heritage Festival
The Halton Asian Heritage Society fills Fowley Park with live performances, food trucks, vendors, games and cultural booths. Free and open to all ages.
🎟️ Free
📅 Sat, Sep 19 | 11AM–7PM
📍 Fowley Park

🏃 Oakville Terry Fox Run
Coronation Park hosts the annual run for cancer research. Registration opens at 9AM with the run starting shortly after, so bring family and friends.
📅 Sun, Sep 20 | Registration 9AM
📍 Coronation Park

☘️ Fall Celtic Festival
Two outdoor days celebrating Irish, Scottish, Welsh, Cornish, Breton, Manx and Celtic Iberian culture, with live performances, demonstrations, exhibits and hands-on workshops.
🎟️ Free
📅 Sat, Sep 26 – Sun, Sep 27 | 9AM–6PM
📍 Toronto Rock Athletic Centre

🐶 Doggie Dip Fest
The sixth annual end-of-summer fundraiser for the Humane Society of Oakville Milton & Halton. Dogs get 30-minute swim sessions at Lions Pool, with the Barkin' Market, vendors and photo ops alongside. Sessions fill quickly.
🎟️ $30 per registration
📅 Sun, Sep 13 | From 10AM
📍 Lions Pool

🎭 Culture Days
The national arts celebration runs across Oakville for two and a half weeks, with free hands-on and behind-the-scenes programming at venues around town.
🎟️ Free events
📅 Fri, Sep 18 – Sun, Oct 4
📍 Various locations across Oakville

🎊 Trafalgar-Chartwell Block Party
Reynolds Street Park hosts a free neighbourhood afternoon with inflatable games, plus a chance to learn what local programs, services and volunteer openings are around.
🎟️ Free
📅 Sat, Sep 19 | 10AM–2PM
📍 Reynolds Street Park

🚗 British Car Day
Over 1,000 British cars and 9,000 spectators fill Bronte Creek for the largest one-day all-British car show in North America, hosted by the Toronto Triumph Club since 1984.
📅 Sun, Sep 20 | 9AM–4PM
📍 Bronte Creek Provincial Park

🧵 World of Threads Festival
Contemporary fibre and textile art from 192 artists across 22 countries opens at QEPCCC and runs through the winter. The festival is free.
🎟️ Free
📅 Sep 23 - Jan 17
📍 Queen Elizabeth Park Community and Cultural Centre

🎃 Harvest Festival
Spruce Lane Farm turns the clock back a century for two days of demonstrations, apple cider pressing, tours of the 124-year-old farmhouse and pick-your-own pumpkins by donation.
📅 Sat, Sep 26 – Sun, Sep 27 | From 10AM
📍 Bronte Creek Provincial Park

🖨️ Print Expo & Fair
Howard Iron Works opens its printing museum for tours, live demonstrations, hands-on printing and the Canadian Letterpress Alliance gallery.
📅 Sat, Sep 26 | 10AM–4PM
📍 Howard Iron Works Printing Museum

🖼️ Ali Cherri: To Fall, Patiently
Films, sculptures and watercolours spread across both Oakville Galleries spaces and the grounds at Gairloch Gardens, from an artist shaped by the postwar Beirut art scene of the 1990s.
🎟️ Free
📅 Now – Sat, Oct 3
📍 Gairloch Gardens

🎵 Bronte Lake Notes
The last night of the summer series at the Sails Stage, free live music by the harbour with room to dance.
🎟️ Free
📅 Thu, Sep 3 | 7PM–9PM
📍 Bronte Heritage Waterfront Park, Sails Stage

💃 Bronte's Dominican Bachata Party
Two Fridays left in the 13-week run at Bronte Market Square, free all-ages dancing led by Tiana Adames.
🎟️ Free
📅 Fri, Sep 4 & Fri, Sep 11 | 6:30PM
📍 Bronte Market Square, 2445 Lakeshore Rd W

📖 The Literary Hub Poetry Reading
Five poets read at the Central Branch: John Oughton, Josie Di Sciascio-Andrews, Paul Edward Costa, Irina Moga and Susan Ksiezopolski.
🎟️ Free
📅 Wed, Sep 2 | 6PM–7:30PM
📍 Oakville Public Library, Central Branch

🎨 Nyikos, Flaherty & Mondock Group Show
Summer & Grace Gallery opens a three-artist exhibition with a reception on Church Street. Come meet the artists.
🎟️ Free
📅 Thu, Sep 10 | 5PM–7PM
📍 323 Church Street

🎸 ØRGANEK
One of Poland's best-known alternative rock bands plays the Oakville Centre, with Juno-winning Canadian soul and R&B artist Sean Jones opening.
🎟️ $79
📅 Fri, Sep 11 | 8PM
📍 Oakville Centre, AEG Liebherr Auditorium

🌷 Art in My Garden
Over 65 local artists set up across 35 private gardens in Old Oakville for a free outdoor exhibit near the lake. Wander, meet the artists, and take your time.
🎟️ Free
📅 Sat, Sep 12 | 12PM–3PM
📍 Gardens around Old Oakville

🎻 Umm Kulthum 2
The Music Without Borders Ensemble for Arabic Music returns with new arrangements of the Star of the East's best-loved works.
🎟️ $39–$56
📅 Sun, Sep 13 | 7PM
📍 Oakville Centre, AEG Liebherr Auditorium

📚 In Conversation With Liane Moriarty
The author behind Big Little Lies talks about her new sequel and the family dynamics running through her work.
🎟️ $15, or $50 with a copy of the book
📅 Thu, Sep 17 | 7PM
📍 Oakville Centre for the Performing Arts

🎭 God of Carnage
Yasmina Reza's play about two sets of parents meeting over a playground fight, back by popular demand in the Studio Theatre under director Yo Mustafa. Evening and matinee performances.
🎟️ $32
📅 Fri, Sep 18 – Sun, Sep 20
📍 Oakville Centre, Studio Theatre

⛰️ Banff Centre Mountain Film Festival
The world tour of one of the biggest mountain festivals anywhere stops at the Oakville Centre for a night of adventure film.
🎟️ $25
📅 Sat, Sep 19 | 7PM
📍 Oakville Centre for the Performing Arts

✍️ Author Talk with Wiley Wei-Chiun Ho
The first salon of the fall season at Summer & Grace, a conversation with the author of the debut memoir The Astronaut Children of Dunbar Street.
🎟️ $20
📅 Tue, Sep 22 | 7PM–9PM
📍 323 Church Street

💅 Mean Girls the Musical
BurlOak Theatre brings the film to the stage with sharp comedy, big musical numbers and all of North Shore High's social politics intact. Evening and matinee performances, best suited to ages 13+.
🎟️ $44
📅 Thu, Sep 24 – Sun, Sep 27
📍 Oakville Centre, AEG Liebherr Auditorium

🕯️ Candlelight: Vivaldi's Four Seasons
A string quartet plays all four concertos plus "La Follia" by candlelight at Knox Presbyterian. The programme runs 60 minutes.
🎟️ From $39
📅 Fri, Sep 25
📍 Knox Presbyterian Church, 89 Dunn Street

🕯️ Candlelight: Queen vs. ABBA
Same church, same candles, different setlist. String-quartet arrangements of "Dancing Queen," "Mamma Mia," "Waterloo" and more.
🎟️ From $39
📅 Fri, Sep 25
📍 Knox Presbyterian Church, 89 Dunn Street

🥁 Veronica Johnny & The Johnnys
The Centre's Truth and Reconciliation programme. Veronica Johnny is an Indigi-Queer Cree-Dene singer, songwriter and hand drummer, opening solo before the full band takes over after intermission.
🎟️ Free, complimentary tickets available
📅 Wed, Sep 30 | 7PM
📍 Oakville Centre for the Performing Arts

🥕 Oakville Civitan Farmer's Market
Oakville's longest-running farmers market keeps going every Saturday at Dorval Crossing. Stall rental proceeds go to local charities.
🎟️ Free
📅 Sep 5, 12, 19, 26 | 8AM–1:30PM
📍 Dorval Crossing

🃏 Card Yard
A one-day collectibles convention for trading card games, sports cards and comics, with vendors on hand to buy, sell and trade.
🎟️ Free
📅 Sat, Sep 5 | 11AM–5PM
📍 OE Banquet & Conference Centre

🥫 OCA Trunk Sale and Food Drive
The Oakville Community Association runs a trunk sale at the Holiday Inn. Shop the trunks and bring something for the food drive while you're there.
📅 Sat, Sep 19 | 9AM–2PM
📍 Holiday Inn Oakville Centre, 590 Argus Road

♻️ REmarket Oakville
Oakville's first reuse and recycling market, where you can recycle hard-to-dispose items and take part in a FreeMarket give-and-take. Parking at the park is free.
🎟️ Free
📅 Sat, Sep 19 | 9AM–2PM
📍 Bronte Heritage Waterfront Park

🌸 Oakville Women Expo
The third annual expo brings together women-owned local businesses for shopping, networking and community connection. Vendor spots are full, but admission is free.
🎟️ Free
📅 Sun, Sep 20 | 11AM–4PM
📍 Hilton Garden Inn Oakville

🛍️ Fall Shop The Street
Downtown Oakville's shops move out onto the sidewalk for the weekend. Stroll the neighbourhood and see what the local retailers put out.
📅 Sat, Sep 26 – Sun, Sep 27
📍 Downtown Oakville

🧶 Artisan Bazaar Fall Craft Show
A curated handmade market making its Oakville debut, with small-batch goods and one-off pieces from Ontario artisans.
📅 Sat, Sep 26 | 10AM–4PM
📍 St. Volodymyr Event Centre

🖌️ Paint Nite at Dave & Buster's
Arpitha R walks the room through a lakeside sunset painting step by step. Supplies included, no experience needed, ages 13 and up.
🎟️ $47
📅 Thu, Sep 3 | 7PM–9PM
📍 Dave & Buster's Oakville

☕ Brew Lab: Discover Specialty Coffee
Ninety minutes of guided tasting with Poets & Prose Coffee Roasters, covering where coffee is grown and how it is processed. Built for beginners and curious drinkers.
🎟️ $23–$40
📅 Sat, Sep 5 | 9AM–10:30AM
📍 2140 Winston Park Drive

🔔 Sound Bath & Energy Activation
Two hours of guided meditation, breathwork, gentle movement and sound at INYE Yoga, co-facilitated by two certified practitioners.
🎟️ $82
📅 Sun, Sep 6 | 2:30PM–4:30PM
📍 INYE Yoga

💛 Halton Memory Café
A relaxed monthly gathering for people living with dementia and their care partners, with conversation and light activities. Space is limited, so register ahead.
🎟️ Free
📅 Wed, Sep 9 | 10AM–11:30AM
📍 Glen Abbey United Church

🍷 Taste & Paint: An Evening of Wine and Art
Make an acrylic painting at Oakville Galleries while tasting two premium Niagara wines, one white and one red, with local charcuterie alongside.
📅 Fri, Sep 11 | 6:30PM–9PM
📍 The Studio at Oakville Galleries

🚶 STRONG Oakville Community Walk
An evening walk on the Lions Valley trails, built around moving and meeting people rather than pace. Free, but register so they know who's coming.
🎟️ Free
📅 Sun, Sep 13 | 5PM
📍 Lions Valley Park

👜 DIY Collage Tote Bag Workshop
She's So Bookish hosts a books-and-coffee themed evening of tote decorating at MOTW. Tote, supplies and one drink are included.
🎟️ $33
📅 Mon, Sep 14 | 6:30PM–8:30PM
📍 MOTW Coffee & Pastries, 335 Kerr Street

🎨 Introduction to Painting with Wayne Moore
A five-week beginner course covering value, colour mixing, paint properties and building form. Students pick their own subject and finish a piece.
🎟️ $180
📅 Fridays · Sep 18 – Oct 16 | 1PM–4PM
📍 Joshua Farm Gallery

🍞 Bake & Connect: Sourdough Workshop
Hands-on sourdough baking at Taste of Colombia, with coffee, premium olive oil tasting and snacks built into the afternoon.
🎟️ $125
📅 Sun, Sep 20 | 2PM–5PM
📍 Taste of Colombia, 67 Bronte Road

🏁 Oakville Cruze Night Classic Car Shows
The Lions Club's weekly cruise wraps for the season on Sep 16, with classic cars, live music, door prizes and a 50/50 draw. Weather dependent.
🎟️ Free
📅 Wednesdays · Sep 2, 9, 16 | 6PM
📍 Oakville Place parking lot

🚶 Walk & Talk History
Historian Maryanne Mason leads a guided tour of Bronte Village and the people behind it. Walks leave from Sovereign House and you need to register by email in advance.
📅 Sep 9 & 23 | 1:30PM
📍 Meet at Sovereign House

🎲 Games Night at the Cafe
The Halton Down Syndrome Association takes over BU Cafe for an evening of board games, new faces and coffee.
📅 Fri, Sep 4 | 6PM–8PM
📍 BU Cafe & Market

🤝 Punjabi Chamber West GTA Launch Social
The Punjabi Chamber of Commerce marks its extension into Oakville with an evening of food and new connections at Milestones.
📅 Thu, Sep 10 | 6PM–8:30PM
📍 Milestones

🎣 Bronte Classic
The Halton Region Salmon & Trout Association's flagship tournament, capped at 51 boats and sold out in recent years. Competitive teams and recreational anglers both enter.
📅 Sat, Sep 12 | 5:30AM–2PM
📍 Bronte Harbour

🍛 Cookbook Club
The library's food-themed book club takes on Indian vegetarian cooking this month. Read something from the list, try a recipe, come talk about it.
🎟️ Free
📅 Wed, Sep 16 | 7PM–8PM
📍 Iroquois Ridge Branch

🏛️ Speaker Night: What Our Buildings Say About Us
Shannon Kyles looks at how waves of settlement across Ontario show up in the architecture, and what that says about the economics and values of each era.
📅 Wed, Sep 16 | 7:30PM–9:30PM
📍 The Coach House

💜 Take Back the Night
SAVIS of Halton's 37th annual gathering stands with survivors of gender-based and sexual violence, with an outdoor community marketplace of local services beforehand.
📅 Thu, Sep 17 | 6PM–9PM
📍 Film.Ca Cinemas

🥣 Saturday Morning All-You-Can-Eat Cereal Cartoon Party
Film.Ca and V!VA Oakville put on cereal and cartoons, screening Tom & Jerry: Forbidden Compass. Bring your own bowl if you can.
📅 Sat, Sep 19 | Doors 9:30AM, movie 10AM
📍 Film.Ca Cinemas

🏅 motionball Marathon of Sport
Teams pair up with local Special Olympics athletes for a day of soccer, basketball, benchball and more at Appleby College, raising money for the Special Olympics Canada Foundation.
🎟️ $50 to register
📅 Sun, Sep 20 | 9AM–3PM
📍 Appleby College

🐾 Barkday Social
Dogs and their people take over Town Square for an afternoon of treats and mingling.
🎟️ Free
📅 Sun, Sep 20 | 11AM–2PM
📍 Oakville Town Square

🍽️ The PARTY: Dinner in Gairloch Gardens
Back for the first time since 2019, a tented dinner overlooking Lake Ontario supporting free access programming at Oakville Galleries. Seating is limited and it has sold out in past years.
📅 Thu, Sep 24 | 6PM–midnight
📍 Gairloch Gardens

👒 The Sororum: A Sunday Afternoon in Downtown Oakville
An afternoon starting at Erchless Estate, following the stories of remarkable local women and Oakville's connections to the Underground Railroad. Museum admission and lunch at Paradiso are included.
🎟️ $55
📅 Sun, Sep 27 | 12PM–3PM
📍 Oakville Museum at Erchless Estate, 8 Navy Street

🔮 Beyond The Veil: Live Psychic and Mediumship Readings
Medium Barbara Quinton does live audience readings over 90 minutes at STACK BBQ. Dinner service opens at 5:30PM for ticket holders.
🎟️ $55
📅 Tue, Sep 29 | 7PM–8:30PM
📍 STACK BBQ Smokehouse