Events happening in Oakville.

Friday, August 21st

9:30AM – 5:00PM

SENIOR ACTIVITIES - INDEPENDENCE DAY CRUISE - 70TH PARISH CELEBRATION

Boat Cruise on the Grand River 🚤 Join a day-long cruise on Friday, August 21st. The boat features an enclosed dining room, a promenade deck with seating, and wheelchair-accessible washroom facilities. All guests receive a full meal service with live Blazing Fiddle Show entertainment. The menu includes complimentary refreshments upon arrival (coffee, tea, selection of muffins), home-baked bread, garden salad with choice of dressing, and a choice of main courses: slow-cooked roast beef and gravy, baked boneless chicken breast with potatoes and vegetables, or Moroccan vegetable bean soup with vegetable samosa and rice (vegan). Dessert options are Apple Crumble Pie, Classic Cheesecake, or Gluten-Free Brownie. Tea, coffee, and soft drinks are included. Meals are pre-plated and served to your table. Gluten-free and vegan options are available but must be pre-ordered. Bar service offering beer, wine, and basic mixed drinks is available on board. Payment options: cash, credit, or debit. No outside food or drink is permitted. Meet at the church at 9:45 AM; departure is at 10 AM.

· Free

Friday, August 21st

11:00AM – 12:00PM

A Large Slow River: Janet Cardiff’s Audio Walk in Gairloch Gardens

Oakville Galleries invites visitors to experience Janet Cardiff's immersive outdoor audio walk, A Large Slow River, at Gairloch Gardens. Commissioned in 1999 and recorded live on-site, the work responds directly to the landscape, creating a sensory experience that encourages visitors to slow down, observe, and listen closely. The walk is drop-in; no registration required. MP3s are provided. Headphones and audio equipment are available to borrow from the front desk, or visitors may bring their own (Bluetooth compatible). After the walk, visitors are welcome to linger in the gardens, purchase light refreshments and bites from local vendor Chuchos Churros, and visit the current exhibition Ali Cherri: To Fall Patiently. Accessibility: The outdoor audio walk includes outdoor pathways, garden terrain, and stairs, and may not be fully accessible for all visitors. Those with mobility concerns are encouraged to contact Oakville Galleries in advance to discuss possible accommodations.

Oakville Galleries in Gairloch Gardens · Free

Friday, August 21st

6:30PM

Bronte's Dominican Bachata Party 2026

Bachata Nights 💃 at Bronte Market Square runs for 13 weeks this summer, offering free dance celebrations for all ages. Tiana Adames leads the sessions, bringing rhythm and community spirit to the heart of Bronte. Attendees are invited to dance along.

Bronte Market Square – 2445 Lakeshore Rd W

Friday, August 21st

7:00PM

Friday Night Jazz

Live jazz every Friday from 7:00 p.m. to 9:00 p.m., starting June 5th. 🎶 John Canham and friends perform throughout the summer.

Towne Square

Friday, August 21st

7:30PM – 9:00PM

el cuadro flamenco 💃🏾

el cuadro F l a m e n c o Date: August 21, 2026, 7:30 - 9:00 p.m. Location: Taste of Colombia. 67 Bronte Road, Oakville Four global artists unite in the percussive and vibrant art of Flamenco. The 4 components of Flamenco ( song, guitar, dance and rhythm ) traditionally form a conversation, with each artist listening and responding, letting the soulful music lead them to the breaks and phrases of complicated and rhythmic time signatures. A style that takes you back in time to the traditions of small gathering and jam sessions in the Flamenco barrios of Andalusia. More info .

Taste of Colombia - Fair Trade Coffee & Gift Shop · $35.00 + hst

Friday, August 21st

8:00PM – 9:30PM

Kill Tony Kansei Yasuda Live Comedy at Oakville August 21 @Moonshine cafe

Kansei Yasuda, a Kill Tony Golden Ticket winner, delivers a 40–45 minute stand-up set of slow-burn comedy, absurd jokes, and sharp punchlines. Known for his calm, deadpan delivery and unexpected perspective, Kansei blends awkward honesty with observations that sneak up on audiences. Originally from Tokyo and now based in Toronto, he has performed across North America and opened for Adam Ray. The show opens with a few comedian friends performing before Kansei takes the stage. Follow Kansei on Instagram @kanseicomedy and watch his Kill Tony appearances on YouTube at https://www.youtube.com/@kanseicomedy

The Moonshine Cafe · $25 CAD

Saturday, August 22nd

8:30AM – 4:30PM

Steps 4 Hope Walk Donor Drive 4 Dorothy

Donor Drive 4 Dorothy (DD4D) is a Black-led Canadian charity growing the stem cell registry and supporting blood cancer patients. Steps4Hope 5K Walk takes place Saturday, July 18 at Bronte Heritage Waterfront Park in Oakville. The event is pet-friendly and family-friendly, welcoming walkers of all ages and abilities. Proceeds support stem cell donor registration and blood cancer patient support.

Bronte Heritage Waterfront Park

Saturday, August 22nd

9:00AM

Summer Sweat

Summer Sweat brings outdoor fitness classes to Downtown Oakville every Saturday morning at 9 AM in Towne Square, led by local fitness businesses. Classes range from hot yoga and pilates flows to high-energy spin sessions. Scheduled classes: August 15: Hot Yoga & Pilates August 22: D Studios (sessions at 9 AM, 10 AM, and 11 AM) August 29: Two Sisters Pilates (sessions at 9 AM and 10 AM) Registration is required for each class. Additional dates and instructors will be announced.

Towne Square

Saturday, August 22nd

10:00AM – 1:30PM

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

Lead Off Youth Home Run Derby 🏟️ Young hitters ages 14 and under (born 2012 or later) compete in a three-round home run derby at Palermo Park South Diamond in Oakville. Players from house league and rep teams are welcome. The event features two fence distances: 200 feet for 11U–12U players and 225 feet for 13U–14U players. Round 1 consists of 10 swings; hitters who hit at least one home run advance (minimum 10 players advance). The medal round gives the top finishers 10 swings each, with the top 5 advancing to the championship round. The championship round crowns the winner. If a player hits a home run on their final swing in Round 2 or 3, they continue swinging until they do not homer. Ties are broken with 5 swings. Prizes: Champion receives a custom championship ring; 2nd and 3rd place earn silver and bronze medals; 4th–10th place receive finalist medals. Registration begins at 9:00 AM; first pitch is 10:00 AM on Saturday, August 22, 2026. Pricing: Super Early Bird $35 (limited); Early Bird $39 (until July 1); Regular $45 (after July 1). The event is limited to 25 hitters and is now full; a waitlist is open.

Palermo Park · $35 – $45 CAD

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

Saturday, August 22nd

12:00PM – 8:00PM

Pre Festival Vendors Exhibition

The Pre Festival Vendors Exhibition, hosted by HCCA, showcases handcrafted products and artworks from talented vendors. Attendees will find a diverse range of unique items, including handmade jewelry, paintings, and other creative work. August 22, 2026, at 12:00 PM 1280 Dundas Street West, Oakville

St. Volodymyr Event Centre - SV Event Centre · Free

Saturday, August 22nd

1:00PM – 4:30PM

The Secret Language of Trees: Learn to Communicate with Nature

This half-day session invites participants to explore communication with nature and deepen their connection to the natural world. The session is designed for anyone who feels a deep bond with nature or wishes to reconnect. Participants will learn to communicate with trees and other beings of the Earth, discovering how they can serve as teachers, guides, and protectors. The focus is on slowing down, quieting mental noise, and accessing intuition in a natural setting. Participants will walk away with a renewed connection to nature, a stronger relationship with their own intuition, and practical understanding of how to communicate with trees.

Bronte Creek Provincial Park (camping area) · $108.47 CAD

Saturday, August 22nd

1:30PM – 2:30PM

⚾ Lead Off Future Stars Home Run Derby (8U–10U) | Oakville

Lead Off Future Stars Home Run Derby 🏟️ Young hitters ages 10 and under (born 2016 or later) are invited to step up to the plate in this home run derby competition. All players are welcome — house league and rep players alike. Participants will compete at a 115-foot fence, ideal for 8U–10U players. Round 1 requires hitters to hit one home run within 10 swings to advance. The championship round gives each finalist 10 swings to hit as many home runs as possible; if a player homers on their final swing, they continue until they fail to homer. Ties are broken with 5 additional swings. The champion receives a custom championship medal. Saturday, August 22 at Palermo Park South Diamond in Oakville. Registration begins at 12:30 PM; first pitch is at 1:30 PM. Early bird registration (until July 22): $19. Regular registration: $24. Spots are limited to 15 participants — register before the price increase.

Palermo Park · $19 – $24 CAD

Saturday, August 22nd

3:00PM

TD Summer Music Series

TD Summer Music Series 🎶 Live music returns to Downtown Oakville all summer long. Attendees can enjoy performances while shopping, dining on patios, and exploring the area. Strolling musicians perform on Lakeshore Road East from 3 PM to 5 PM. Main performances take place at Towne Square from 5 PM to 7 PM. July 4: Rock Classics with Wildbloom Music July 11: Yacht Rock with Get Yachty July 25: R&B and Soulful Sounds with Bourbon and Co Aug 1: Top 40 Through the Years with The Motive Aug 8: Country Favorites with Jade Hilton Aug 15: Funk & Disco with Disco Fever Aug 22: Interactive Playlist with Great Canadian Dueling Pianos Aug 29: Classic Sounds from Oakville Symphony Bring a chair and enjoy the evening with friends and family.

Downtown Oakville

Sunday, August 23rd

Arya Samaj Burlington - Annual Picnic

Arya Samaj Burlington's Annual Picnic brings together friends and family for an afternoon of food, games, and outdoor activities. Attendees can enjoy good food, exciting activities, and a relaxed outdoor setting designed for connecting and unwinding together.

Coronation Park

Sunday, August 23rd

1:30PM – 2:30PM

Grand Illusion & Magic Show at Dave & Buster's Oakville

Grand Illusion & Magic Show by Edllusion Entertainment features dazzling grand illusions, sleight-of-hand mastery, and interactive moments. The high-energy performance combines mystery and wonder with moments designed to engage audiences of all ages. The show includes grand illusions, close-up sleight-of-hand, and interactive segments that invite audience participation. Individual admission is $20. A Family 4 Pack is available for $99.99 (listed value $120). Power Cards and drink ticket add-ons are available for purchase. Arrive at any time on the day of the show to enjoy arcade gameplay at Dave & Buster's before the performance. Check in at the front desk upon arrival. All children must be accompanied by an adult. All adults require a ticket for entry. Children under 2 do not need a ticket but will not receive a Power Card. Once purchased, all tickets are non-refundable and non-transferable. Restrictions may apply; see the store for details. Questions: Contact Paige Moyce at 289-807-0356 or paige.moyce@daveandbusters.com.

Dave & Buster's Oakville · $22.90 – $108.46 CAD

Sunday, August 23rd

2:30PM – 4:30PM

Taller para mamás: Hábitos Anti-inflamatorios

A workshop for mothers seeking to reduce inflammation and recover energy through natural eating habits, including hands-on cooking. Many women live with fatigue, inflammation, chronic pain, allergies, digestive issues, or anxiety, believing these are simply part of motherhood or aging. This workshop invites participants to listen to their bodies instead. It is not a trendy diet class, a technical lecture, or prescriptive meal planning — it is an experience designed to help understand body signals, discover habits that may fuel inflammation, and make simple, real, sustainable changes. The workshop is for anyone who wants to understand their body better and care for it from a different perspective. No diagnosis is required. Astrid González, a Health Coach and founder of Astrid Natural Life, will share her personal story: living with asthma and allergic rhinitis from childhood, she discovered that many normalized symptoms were linked to inflammation and unexamined habits. The discussion will cover food and lifestyle's influence on energy, wellbeing, and health — without creating a list of forbidden foods. Participants will leave understanding why their body may be sending certain signals and what first steps can truly make a difference. After the talk, there will be an open space to share questions, discuss individual situations, and hear from other women facing similar challenges. The workshop aims to build a safe, judgment-free community where participants learn from one another. The session will conclude with preparing simple, quick, delicious recipes together using natural ingredients that fit easily into daily routines, even with young children. Participants will taste the food and discuss making anti-inflammatory eating practical for busy family life. Welcoming mothers with babies up to 12 months old. Prelaunch pricing available until Sunday, August 9. Follow @astridnaturallife on Instagram.

Taste of Colombia - Fair Trade Coffee & Gift Shop · $43.23 CAD

Sunday, August 23rd

5:00PM – 9:00PM

West End Jazz Presents: A Tribute to Peggy Lee

The West End Jazz series presents a dinner theatre production. Attendees may choose to enjoy dinner, attend the show only, or both. Doors open at 4:00 PM, dinner is served at 5:00 PM, and the show begins at 6:00 PM. Peggy Lee was an iconic jazz singer and actress, celebrated for her signature sultry vocal style. Her best-known hits include "Fever," "Mañana," and "Is That All There Is?" Shannon Butcher delivers Peggy Lee's songs with remarkable authenticity — closing your eyes, you may feel as though Peggy Lee herself is on stage.

Oakville Conference Centre