Things to do in Oakville in May

📸 Mother's Day Photo Pop-Up
Pop by the Boler Photobooth Van in Towne Square for free photo prints — a fun way to capture the day with the people you love.
🎟️ Free
📅 Sun, May 10 | 12PM–3PM
📍 Downtown Oakville, Towne Square

⛵ The Ship of Tolerance: 2026 Relaunch
Watch the 60-foot anti-war sculpture by Ilya & Emilia Kabakov set sail for the season — featuring new sails painted by 900 local schoolchildren and remarks from Mayor Burton and Ontario's Minister of Tourism.
🎟️ Free
📅 Fri, May 22 | 12PM–5:30PM
📍 Oakville Galleries in Gairloch Gardens

🏎️ Miles for Smiles
30–35 Lamborghinis assemble at Grand Touring Oakville, then drive as a group to Kelso Conservation Area for a family BBQ with kids from Starlight Children's Foundation — followed by a police-escorted parade to a huge Cars & Coffee at Hagerty Garage & Social.
🎟️ Free
📅 Sat, May 23 | 9AM–4PM
📍 Grand Touring Automobiles Oakville, 1311 North Service Road West

🎡 Northeast Oakville Fair
The 7th annual NE Oakville Fair returns with a day of activities, great vibes, and serious community spirit.
🎟️ Free
📅 Sun, May 24 | 11AM–4PM
📍 Glenashton Park, 1051 Glenashton Dr

🚚 Community Living Oakville's Food Truck Friday
A vibrant Towne Square gathering hosted by Community Living Oakville for Community Living Month — two local food trucks, live energy, and a celebration of diversity and inclusion.
🎟️ Free
📅 Fri, May 29 | 12PM
📍 Towne Square, Downtown Oakville

🥕 Oakville Civitan Farmers Market
Oakville's longest-running farmers market kicks off its season — wander the stalls, grab fresh local goods, and know that proceeds support local charities.
🎟️ Free
📅 Every Saturday, May 2 – Nov 28 | 8AM–1:30PM
📍 240 North Service Rd W

🌷 Artisan Pop-Up Market: Mother's Day Edition
Discover handcrafted gifts and unique finds from local makers — perfect for picking up something thoughtful for Mom (or yourself).
🎟️ Free
📅 Sat, May 2 | 10AM–5PM
📍 Taste of Colombia, 67 Bronte Road

🧒 Oakville Youth Market
Shop from young entrepreneurs aged 11–17 showcasing their businesses — support the next generation of Oakville makers.
🎟️ Free
📅 Fri, May 2 | 12PM–4PM
📍 Queen Elizabeth Park Community & Cultural Centre

🏷️ Safetynet Charities Garage Sale
Fill a bag for $20 with clothing, housewares, and toys — every dollar supports Safetynet's free wrap-around services for families in need.
🎟️ $20 per bag
📅 Sat, May 9 | 8:30AM–2PM
📍 166 South Service Rd East

🌾 Gluten-Free Bazaar 2026
Over 30 vendors offering gluten-free baked goods, specialty foods, and lifestyle brands — a full day of sampling, shopping, and community for the GF crowd.
🎟️ Free
📅 Sat, May 9 | 10AM–5PM
📍 Oakville Place, 240 Leighland Ave

🌙 Oakville Eid Bazaar
A vibrant day of shopping, delicious food, and family fun — celebrating Eid with the whole community.
🎟️ Free
📅 Sun, May 24 | 2PM–11PM
📍 St. Volodymyr Cultural Centre, 1280 Dundas St W

🌸 Spring Fling Market
Celebrate the season at this charming farm market — local makers, original art, and one-of-a-kind handmade finds in a beautiful setting.
🎟️ Free
📅 Sat, May 30 | 11AM–3PM
📍 Joshua Farm Gallery, 1086 Burnhamthorpe Rd E

🌸 Mom & Me Bouquet Workshop
Craft a stunning crepe paper bouquet alongside Mom in a cozy downtown coffee shop — a handmade keepsake that'll never wilt.
🎟️ $40–$55
📅 Thu, May 7 | 6:30PM–9:30PM
📍 Figaro Coffee House, 350 Lakeshore Rd E

🍰 Mother's Day High Tea & Live Music
A refined Persian high tea at Narenj — savoury bites, handcrafted sweets, refillable teapots, and live music from Sina to set the mood.
🎟️ $85 per person
📅 Sat, May 9 | 4PM–6PM
📍 Narenj Oakville, 131 Kerr St

🍝 Mother's Day Pasta Making with Chef Enzo Campisi
Learn to handcraft tortelloni and cavatelli from scratch, then sit down to a full meal — pizza tasting, salad, your homemade pasta, and torta della nonna. Wine included.
🎟️ $155 per person
📅 Sat, May 9 | 6:30PM–9PM
📍 Mercato Sociale, 257 Lakeshore Rd E

🍪 Mother's Day Parent & Me Cookie Decorating
A hands-on cookie decorating class designed for kids 4+ and their grown-ups — piping techniques, colourful icing, and sweet memories.
🎟️ $50 per pair
📅 Sun, May 10 | 11:30AM–1PM
📍 TaDa Treats, 2030 Bristol Circle

🍷 Mother's Day Cookie Decorating with Wine
Decorate themed cookies while sipping champagne in a relaxed, judgment-free workshop — perfect for moms, partners, friends, or solo flyers.
🎟️ $65 per person
📅 Sun, May 10 | 2PM–4PM
📍 TaDa Treats, 2030 Bristol Circle

🎷 Mother's Day Chef's Tasting & Jazz Night
A tapas-style chef's tasting menu with wine or cocktail pairings, plated dessert by Chef Dustin Sze, and live jazz from Dyanne Dumas and her band.
🎟️ $110 per person
📅 Sun, May 10 | 6PM–8PM
📍 Narenj Oakville, 131 Kerr St

🎤 Halfway2Summer: Afrobeats Show at Fratelli's
Part of the Championship tour — catch YBAfrmdaJane, Valintino, Swish and more for a high-energy Afrobeats night.
🎟️ From $15
📅 Fri–Sat, May 1–2 | 9PM–2AM
📍 Fratelli's, 316 Kerr Street

🎶 Symphonies of Bollywood
A live concert from the Bollywood Karaoke Club — sing your heart out to Bollywood hits with five headline performers and fellow fans.
🎟️ $22 per ticket
📅 Sun, May 3 | 2PM–6PM
📍 Forestview Church Without Walls, 3175 Dundas St W

🎵 The Circle Game: Oakville Youth Choir Spring Concert
The Oakville Choir's spring concert is inspired by Joni Mitchell's iconic song — a narrative journey through childhood, growth, and the seasons of growing up.
🎟️ From $22.63
📅 Wed, May 6 | 6:30PM  •  Sat, May 9 | 3PM
📍 St. John's United Church, 262 Randall St

📷 Memories of Old Grumpy Vlad: Photography Exhibition
Experience a lifetime of moments through the lens of award-winning photographer Vladimir Kabelik — this exhibition marks the end of his career, with archival prints exclusively available.
🎟️ Free
📅 Thu, May 7 | 5:30PM–8:30PM
📍 Savvy Art, 33 Shepherd Rd, Unit 100

🎭 Tarweeda
A captivating theatrical performance celebrating Palestinian women through song, movement, and storytelling — rooted in folk traditions that carried joy, longing, and defiance across generations.
🎟️ $18 (kids 12 & under) / $34 (regular seating)
📅 Sun, May 10 | 6:30PM
📍 Oakville Centre for the Performing Arts, 130 Navy St

🎤 Funny at Figaro: Comedy Open Mic
Drop in to catch local comics trying out new material on the second Tuesday of every month. Come for the comedy, stay for the food and drinks.
🎟️ Free
📅 Tue, May 12 | 8PM
📍 Figaro Coffee House, 350 Lakeshore Rd E

🎨 Landscape Botanicals Paint & Sip
An adults-only creative evening at Gairloch Gardens — learn painterly techniques to capture botanical scenes with guidance from instructor Emma. All materials provided, no experience necessary.
🎟️ $55.25 members / $65 non-members
📅 Thu, May 21 | 6:30PM–8:30PM
📍 Oakville Galleries in Gairloch Gardens

🎻 OMEF Charity Music Night
An evening of professional music featuring Chinese instruments, vocals, and dance — plus a silent auction. All proceeds benefit Oakville Trafalgar Memorial Hospital.
🎟️ From $12
📅 Sat, May 23 | 7PM–9PM
📍 Glen Abbey United Church, 1469 Nottinghill Gate

🎙️ Apne: Volume 2
After a sold-out debut, Apne returns with headliners SEHER and Zeeshan Ali — soulful vocals, raw talent, and high energy in an intimate setting.
🎟️ From $15.41
📅 Fri, May 29 | 7PM–10PM
📍 Fratelli's, 316 Kerr Street

🍸 Shots of History: Stories with Spirit
A spirited finale to Museum Month — wander through historical vignettes, sip bespoke cocktails crafted by Majestic Wine Cellars, and explore a companion exhibit on the history of alcohol in Oakville.
🎟️ $95.77
📅 Fri, May 29 | 7PM–9PM
📍 Oakville Museum, 8 Navy St

🎹 An Evening of Calming and Reflective Solo Piano Music
Composer/pianist Robert Bruce performs an intimate evening of calming, reflective solo piano in a beautiful church setting.
🎟️ $25
📅 Fri, May 29 | 7:30PM–9PM
📍 St. Jude's Anglican Church, 160 William St

🎼 Carmina Burana by Carl Orff & Works by Brahms
A monumental community collaboration — Masterworks of Oakville Chorus & Orchestra joins forces with Bach Elgar Choir, Georgetown Bach Chorale, and the Oakville Choir for Children & Youth.
🎟️ Free under 30 years old, $38 general admission
📅 Sat, May 30 | 8PM  •  Sun, May 31 | 3PM
📍 St. Matthew Catholic Church, 1150 Monks Passage

🃏 Oakville Pokémon & TCG Card Show
A chill, in-person day for trading, battling, and hunting down rares — meet fellow hobbyists, discover cool cards, and dive into your favourite TCG scene.
🎟️ Free (entry & parking)
📅 Sun, May 3 | 10AM–4PM
📍 Era Event Venue, 2496 Bristol Circle

🎆 Victoria Day Fireworks at Crusaders Rugby Club
The Crusaders' annual Victoria Day fireworks display — bring family and friends for an afternoon and evening of food, drinks, face painting, and a knockout fireworks show.
🎟️ $5/person or $20/car (up to 5 people)
📅 Sun, May 17 | 4PM
📍 Crusaders Rugby Club, 2214 Ninth Line

🏃‍♀️ Shoppers Drug Mart® Run for Women
1K, 5K, and 10K distances at Bronte Creek Provincial Park supporting women and girls' mental health programming at Halton Healthcare. Entry includes a day pass for the park.
🎟️ From $65
📅 Sat, May 23 | 9:45AM
📍 Bronte Creek Provincial Park, 1219 Burloak Drive

🎨 Art on the Bluffs
A bi-weekly showcase of local Bronte artists at historic Sovereign House — featuring oil, watercolour, sculpture, fabric arts and more, with artists often on site to chat about their work.
🎟️ Free
📅 Opens Sun, May 23
📍 Sovereign House, 7 West River Street

🔮 Oakville Psychic & Crystal Fair
A weekend of psychics, mediums, runes, palmistry, crystals, and handmade jewelry — connect with practitioners and explore intuitive arts.
🎟️ $13.54 weekend pass (12 & under free)
📅 Fri, May 29 – Sun, May 31 | Doors 12:45PM
📍 Galaxy 707 Club, 475 North Service Road East

🃏 Card Yard Trading Card Tournament
A buy/sell/trade event for collectibles — TCGs, sports cards, sports memorabilia, comics, and toys. If you collect it, someone here has it.
🎟️ From $60
📅 Sat, May 30 – Sun, May 31 | 11AM–6PM
📍 OE Banquet & Conference Centre, 2245 Speers Road

🎖️ Bronte Legion D-Day Parade
A solemn parade and ceremony honouring the bravery of those who served on D-Day. Refreshments at the Bronte Legion follow the ceremony — everyone welcome.
🎟️ Free
📅 Sun, May 31 | 10:30AM parade  •  11AM ceremony
📍 The Bronte Legion

🎎 Asian Heritage Festival
A day of food, drinks, snacks, captivating performances, and demonstrations celebrating Oakville's vibrant Asian communities — a carnival of culture, dance, and tradition.
🎟️ Free
📅 Sat, May 31 | 11AM–7PM
📍 Fowley Park

👶 Stroller Socials
A caregiver-friendly start to the day — meet other parents for a scenic walk through Downtown Oakville, followed by a guided stretch hosted by Via Pilates.
🎟️ Free (registration required)
📅 Every Thursday, May 14 – June 4 | 8:30AM–9:10AM
📍 Via Pilates, 109 Dunn Street

🚶 Golden Morning Walks
A senior-friendly stroll through Downtown Oakville, followed by a visit to Trafalgar Lodge — perfect for connecting with neighbours and getting moving.
🎟️ Free (registration required)
📅 Every Tuesday, May 12 – June 2 | 9AM–9:40AM
📍 Amenida Trafalgar Lodge, 299 Randall Street

🌟 National Youth Week
A week of free, interactive activities for teens (ages 13–17), capped off by the Oakville Youth Awards on May 7 at the Oakville Centre.
🎟️ Free
📅 May 1 – 7
📍 Various locations across Oakville

📚 Asian Heritage Month: Author Meet & Greet
Storytimes, picture books, and a hands-on craft session with authors Catherine Little, Sunshine Punzalan, and Evelyn Sue Wong — celebrating Asian voices and traditions.
🎟️ Free
📅 Fri, May 2 | 1PM–3PM
📍 Oakville Public Library – Iroquois Ridge Branch, 1051 Glenashton Drive

🌱 Fresh Finds: Spring Cooking Workshop
Explore light, garden-inspired recipes from the Oakville Museum archives with Chef Laura Strath — a hands-on talk, demo, and tasting (ages 12+).
🎟️ $56.84
📅 Sat, May 2 | 1:30PM–4PM
📍 Oakville Museum Coach House, 8 Navy Street

✨ Spring Radiance Holistic Healing Fair
A heart-centered marketplace featuring readers, makers, healers, crystals, natural products, and free workshops — plus swag bags for the first 30 attendees.
🎟️ Free (donations welcomed)
📅 Sun, May 3 | 10AM–4PM
📍 Galaxy 707 Club, 475 North Service Road East

💆 Oakville Beauty, Health & Wellness Expo
The 1st Annual edition of this premier shopping event — discover clean beauty, holistic health, and self-care essentials from local vendors and premium brands.
🎟️ Free
📅 Sun, May 3 | 11AM–4PM
📍 Hilton Garden Inn, 2774 South Sheridan Way

🌸 Women's Circle for Expression & Expansion
A grounding gathering for women to share, reflect, and connect through guided practices in a supportive setting.
🎟️ $33
📅 Sun, May 3 | 4PM
📍 Oakville

🌮 Tacos, Tequila & Wine Glass Painting
Sip, snack, and get creative — paint your own wine glass while enjoying tacos and tequila in a fun, social setting.
🎟️ $33.28
📅 Mon, May 5 | 6PM
📍 STACK BBQ Smokehouse, Oakville

🎨 SensoryLis Art Class
A mindfulness-based art class with instructor Lisaura Lobo — prepare body and mind, learn artistic skills, and tap into creative self-expression.
🎟️ $50 + HST
📅 Sat, May 9  •  Sat, May 23 | 10AM–12:30PM
📍 Joshua Farm Gallery, 1086 Burnhamthorpe Road East

🫖 Hidden Treasures Tea & Tour
A guided tour of Erchless Estate highlighting rarely-seen artifacts, followed by a tea experience and curator presentation in the Coach House.
🎟️ $35
📅 Sat, May 9 | 11:30AM  •  2:30PM
📍 Oakville Museum, 8 Navy Street

🐑 Spring Time on the Farm
Celebrate the arrival of spring like a Victorian — sheep shearing demos, farm activities, and Victorian Tea services courtesy of Friends of Bronte Creek.
🎟️ Free with park admission
📅 Sat, May 16 | 10AM–4PM
📍 Bronte Creek Provincial Park, 1219 Burloak Drive

🍝 Pasta Making with Chef Enzo Campisi
A hands-on Italian evening at Mercato Sociale — learn to make fresh pasta from scratch with Chef Enzo, then enjoy a family-style dinner with wine and dessert.
🎟️ $155
📅 Fri, May 22 | 6:30PM–9PM
📍 Mercato Sociale, 257 Lakeshore Road East

🌷 Tots n' Pots
A drop-off gardening program for ages 3–5 — craft, plant seeds, and explore the historic gardens at Erchless Estate.
🎟️ $50.36 (Oakville resident) / $60.36 (non-resident)
📅 Fri, May 22  •  Fri, May 29 | 9:45AM–11:45AM
📍 Oakville Museum, 8 Navy Street

🍞 Bake & Connect: Sourdough Bread-Making Workshop
Learn the secrets to making your own sourdough loaf from scratch — take home a starter, recipe, and your mixed dough to bake.
🎟️ $125
📅 Sun, May 24 | 2PM
📍 Taste of Colombia, 67 Bronte Road