Good morning! This is The Oakville Digest, your trusted guide to everything happening in the beautiful town of Oakville, Ontario.
Here is what to expect in today’s issue:
☀️ Why June in Oakville is packed with fun and excitement
✈️ Stranded local man returns home from the Dominican
📅 Some awesome events to keep you busy this weekend!
Thanks for being part of our growing community. Let us know what you loved in today’s issue by replying to this email, and….
Let’s dive in!
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News
🌈 Celebrate June in Oakville with Free Events and Activities
Oakville is kicking off summer with a full lineup of free events and activities to celebrate National Indigenous History Month, Pride Month, Recreation and Parks Month, and Seniors Month. Residents are invited to learn, connect, and get involved all month long.
Take a walk on the Moccasin Trails, join Pride-themed programs, explore splash pads and parks, or take part in the ParticipACTION Community Challenge. Seniors can enjoy creative workshops, info fairs, and drop-in programs at local centres and libraries. There's something happening for everyone this June.
🎤 Rock the Stage This Canada Day
Ready to steal the show? Oakville is giving residents the chance to sing their hearts out live with Rock Star Live, a high-energy band made up of pros from top Canadian acts. Ten lucky winners will take the stage on July 1 at Bronte Heritage Waterfront Park, performing Canadian rock anthems in front of a cheering crowd.
If you're 10 or older and love to sing, post a 30-second karaoke-style video on the Town’s social media with #OakvilleRockStar by June 10. Lyrics will be on screen, so just bring your energy.
Community Spotlight
✈️ Home at Last After Dominican Detention
David Bennett and Jane Wilcox reunited | Chris Arnold/BurlingtonToday
David R. Bennett is finally home in Burlington after spending 71 tense days stuck in the Dominican Republic. What started as a baggage issue spiraled into phony drug charges, court hearings, and weeks of uncertainty. After the charges were dropped and a flurry of last-minute calls and messages, Bennett boarded a WestJet flight home on May 16 and was reunited with his partner, Jane Wilcox, at Pearson Airport.
Despite one last scare at Punta Cana airport, where he was briefly held up again by customs, Bennett made it onto his flight and landed in Toronto just in time for a beautiful long weekend. Since returning, he’s been catching up on sleep, reconnecting with loved ones, and thinking about future travel, closer to home for now. Reflecting on the experience, he says he holds no resentment toward the Dominican Republic, only a deeper appreciation for home and the people who supported him.
🚤 OMSAR Launches New Rescue Vessel and Marks 70 Years of Service
Ramona Leitao | Oakville News
Oakville Marine Search and Rescue (OMSAR) celebrated a major milestone this weekend with the unveiling of a new high-tech rescue boat, Oakville Rescue, and a tribute to 70 years of volunteer service on Lake Ontario. The event brought together volunteers, local officials, and supporters at OMSAR’s Navy Street headquarters.
The new vessel, equipped with advanced navigation and built for more demanding missions, replaces an aging boat that served for over 20 years. Past Commander Cliff Feehan called the upgrade essential for the group’s evolving operations, saying, “It’s more than just a boat—it’s our future.” With help from the Town of Oakville and a local fundraising effort, OMSAR’s legacy of lifesaving service continues stronger than ever.
Weather
Friday, May 30
🌩️ Mostly cloudy with a chance of late-day thunderstorms.
High: 21°C | Low: 10°C
Saturday, May 31
🌥️ Cooler with a mix of sun and clouds.
High: 14°C | Low: 9°C
Sunday, June 1
⛅ Partly sunny and pleasant.
High: 16°C | Low: 9°C
Events
Adult Book Club – Family Lore by Elizabeth Acevedo 10:00 AM - 11:00 AM | May 31 (more info)
Location: Woodside Branch, 1274 Rebecca Street, Oakville
Description: Monthly book discussion for adults featuring Family Lore by Elizabeth Acevedo. Drop-in format, no registration required. Ages 18+
Coffee & Fashion: Sip in Style 11:00 AM - 2:00 PM | May 31 (more info)
Location: Taste of Colombia, 67 Bronte Road, Oakville
Description: Fashion and networking event featuring shopping, styling tips, and coffee chats with local leaders. Prize for best dressed.
Music in the Park 1:00 PM - 3:00 PM | May 31 (more info)
Location: Bronte Heritage Waterfront Park, 2394 Ontario Street, Oakville
Description: Free bucket drumming workshop hosted by Bandology. Open to all ages and skill levels.
The Way of Tea – The Japanese Tea Ceremony 1:00 PM - 2:00 PM | May 31 (more info)
Location: The Oakville Museum, 8 Navy Street, Oakville
Description: Guided demonstration of the Japanese tea ceremony with Momo Tea, followed by a museum tour.
Oakville Galleries 2025 Summer Exhibitions Opening 2:00 PM - 7:00 PM | May 31 (more info)
Location: Oakville Galleries in Gairloch Gardens, 1306 Lakeshore Road East, Oakville
Description: Launch event for Between Heaven and Earth and The Ship of Tolerance featuring installations, performances, and light refreshments.
Cupcake Decorating Workshop 3:00 PM - 4:00 PM | May 31 (more info)
Location: Touchdown Coworking Space, 2030 Bristol Circle, Oakville
Description: Hands-on decorating session for parent-child pairs to create six themed cupcakes. Includes materials, instruction, and refreshments.
Salsa Night in Oakville 6:00 PM - 11:00 PM | May 31 (more info)
Location: Taste of Colombia, 67 Bronte Road, Oakville
Description: Dance the night away to Afro Cuban rhythms with Salsa, Bachata, Cha Cha Cha, and Merengue. Hosted in a fair trade café setting.
Halton-Peel Gutsy Walk 2025 10:00 AM | June 1 (more info)
Location: Bronte Heritage Waterfront Park, 2340 Ontario Street, Oakville
Description: Community walk supporting Crohn’s and Colitis Canada with fundraising and awareness activities for those affected by inflammatory bowel diseases.
Bronte Legion D Day Parade 10:00 AM | June 1 (more info)
Location: The Bronte Legion, 79 Jones Street, Oakville
Description: Commemorative parade followed by a ceremony at the Cenotaph and post-event refreshments at the Legion.
Oakville Celtic Fiddle Orchestra Spring Concert 2025 2:00 PM - 4:30 PM | June 1 (more info)
Location: Glen Abbey United Church, 1469 Nottinghill Gate, Oakville
Description: Afternoon concert featuring jigs, reels, and live performances with special guests from the Graham School of Irish Dance. Fundraiser event supporting local causes.
TCF Halton – Bake Sale & Youth Celebration 2:00 PM - 5:00 PM | June 1 (more info)
Location: OE Banquet & Conference Centre, 2245 Speers Road, Oakville
Description: Youth-led celebration featuring music, games, and a fundraising bake sale. Supports community efforts from the recent Ramadan Campaign.
Sip & Paint: Matisse Inspired Magic 2:00 PM - 4:00 PM | June 1 (more info)
Location: Joshua Farm Gallery, 1086 Burnhamthorpe Road, Oakville
Description: Instructor-led painting session inspired by Matisse’s use of shape and colour. Includes complimentary wine and all materials provided.
COURTX Oakville Soft Opening 10:00 AM | May 31 (more info)
Location: COURTX Oakville, 226 Wyecroft Road, Oakville
Description: Launch of a 100,000 sq. ft. indoor racquet club featuring 10 padel and 9 pickleball courts, plus fitness, dining, retail, and social amenities.
Monday Coffee and Conversation Oakville 10:00 AM - 11:00 AM | June 2 (more info)
Location: The Women's Centre, 1515 Rebecca Street, Oakville
Description: Weekly drop-in for women to connect over coffee and casual conversation. Great for new participants.
Meditation Mondays 10:00 AM - 11:00 AM | June 2 (more info)
Location: Central Branch, 120 Navy Street, Oakville
Description: Guided meditation and breathwork session focused on chakras and mental clarity.
Monday Night Trivia at The Tipsy Fox 7:30 PM - 9:00 PM | June 2 (more info)
Location: The Tipsy Fox Pub & Grill, 478 Dundas Street West, Oakville
Description: Free weekly visual trivia game hosted by ruby PUB TRIVIA. Bring a device for digital scoring.
Pollinator Garden Stewardship 4:00 PM - 5:30 PM | June 3 (more info)
Location: Kingsford Gardens, 2480 Sherwood Heights Drive, Oakville
Description: Volunteer to help maintain local pollinator patches through weeding, mulching, and planting. Held Tuesdays on rotation.
Lululemon Oakville Lakeshore Run Club 6:30 PM - 7:30 PM | June 3 (more info)
Location: George's Square, Sumner Avenue and Reynolds Street, Oakville
Description: Weekly group run open to all levels, hosted by lululemon Oakville. Free to join; registration required.
Speakers Night: Halton County Court House 7:00 PM - 8:00 PM | June 3 (more info)
Location: Halton County Court House, 2431 Dundas Street West, Oakville
Description: Historical talk with author John McDonald on the 1855 construction and legacy of the Halton County Court House.
Spring Stroller Socials 11:00 AM - 12:00 PM | June 4 (more info)
Location: Towne Square, 94 George Street, Oakville
Description: Guided stroller walk through Downtown Oakville followed by coffee and conversation. Registration required.
LeadTribes Oakville 12:15 PM | June 4 (more info)
Location: Milestones Restaurant, 3051 Vega Boulevard, Mississauga
Description: In-person networking event for entrepreneurs to connect, grow, and lead through supportive relationships.
Dance Essentials Class 6:30 PM - 7:30 PM | June 4 (more info)
Location: Taste of Colombia, 67 Bronte Road, Oakville
Description: A weekly movement class focused on strength, flexibility, and technical form. Designed for both dancers and non-dancers to enhance physical conditioning.
Thank You!
Thank you for reading The Oakville Digest! We hope you found this edition helpful and insightful. We’d love to hear your feedback or any event suggestions you’d like us to feature in future issues. Don’t forget to share with friends and family, and we’ll see you Monday!
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