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:

  • 🎠 Northeast Oakville Fair returns this weekend

  • 🎙️ Oakville country star makes waves

  • 📅 An exciting, event filled 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

🎈 Hot Air Balloons, Food Trucks, and Family Fun This Weekend

Oakville News

The Northeast Oakville Fair returns this Sunday, May 25, from 11 a.m. to 4 p.m. at Glenashton Park beside Iroquois Ridge Recreation Centre. Now in its sixth year, this free community event promises something for everyone, with bouncy castles, obstacle courses, face painting, live music, and hot air balloon rides.

Food lovers can enjoy tasty options from Arepa Republic, Curbside Food, and GTA Softee, along with free cotton candy and Film.ca popcorn served by volunteers. Sponsored by local businesses and supported by the Town of Oakville, the fair is a proud display of community spirit.

Ward 6 Councillors Tom Adams and Natalia Lishchyna, along with Mayor Rob Burton, are expected to attend and join in the fun. Organizers hope to see thousands enjoy the festivities, and volunteers, including students from Iroquois Ridge High School, will be there to welcome everyone.

🗂️ Shred Documents, Support Crime Prevention

InsideHalton

Oakville residents can protect their personal information while supporting a good cause at the Shred Event Fundraiser happening Saturday, May 24. Hosted by Crime Stoppers of Halton in partnership with Blue-Pencil Information Management, the event runs from 9 a.m. to 3 p.m. at Halton police headquarters.

Participants are invited to bring unwanted personal or business documents to be securely shredded on-site using Blue-Pencil’s mobile shredding trucks. Donations of any amount are welcomed, with all proceeds supporting Crime Stoppers of Halton’s local safety and awareness initiatives.

The fundraiser aims to help residents guard against identity theft and financial fraud through proper document disposal. Whether you’re clearing out files at home or work, this is a simple and effective way to contribute to community safety in Oakville.

Community Spotlight

💛 Community Raises $4,125 for Halton Women’s Place

Oakville News

In just three days, Oakville readers and local businesses raised $4,125 and donated 15 care packages for Halton Women’s Place. The initiative, part of the Cares Spring Match: Sheltering our Communities campaign, was led by Oakville News in partnership with Canadian Tire Fairview Street. Each care package purchased was matched 13 times thanks to generous local sponsors.

Canadian Tire Fairview Street donated the care packages, with support from businesses including She's Got Leggz, QB Sports Bar Grill Games, Royal LePage - Burloak RE Services, and more. If you missed the campaign, you can still support your local shelter by donating directly.

🎤 Paige Rutledge Nominated for Two CMAO Awards

Oakville’s own Paige Rutledge has earned two nominations at the 13th Annual Country Music Association of Ontario (CMAO) Awards. The rising country artist is up for Album of the Year and Breakthrough Artist of the Year, thanks to the success of her EP Break Up Rules, which explores the emotional journey of moving on after a relationship.

“This is my first year being nominated so it is exciting to have not only one nomination but two,” said Rutledge. Inspired by her grandfather’s love of classic country, she grew up listening to legends like Shania Twain and Johnny Cash. The CMAO Awards take place on Sunday, June 1.

Weather

Friday, May 23
🌧️ Periods of rain.
High: 12°C | Low: 8°C

Saturday, May 24
🌥️ Mainly cloudy with a chance of showers.
High: 14°C | Low: 8°C

Sunday, May 25
⛅ Partly cloudy with a chance of afternoon showers.
High: 15°C | Low: 8°C

Events

  • Revelations | Spring Art Show Multiple Times | May 24–August 29 (more info)

    • Location: Queen Elizabeth Park Centre, 2302 Bridge Road, Oakville

    • Description: Group art exhibition exploring personal transformation and insight through diverse works

  • City Dance Corps Open House - Multiple Times | May 24 (more info)

    • Location: City Dance Corps, 2630 Bristol Circle, Oakville

    • Description: Free dance classes in all styles and levels as part of City Dance Corps' 23rd anniversary celebration

  • Smilezone Celebrity Hockey Tournament 9:00 AM - 4:30 PM | May 24 (more info)

    • Location: Joshua’s Creek Arenas, 1663 North Service Road East, Oakville

    • Description: Full-day hockey event with celebrity players, shootouts, food trucks, face painting, balloon artists, live music, and more.

  • Halton Walk for Alzheimer's 10:00 AM - 12:00 PM | May 24 (more info)

    • Location: Bronte Heritage Waterfront Park, 2340 Ontario Street, Oakville

    • Description: Community walk and fundraiser supporting dementia care and services in Halton region

  • Asian Heritage Festival 2025 11:00 AM - 7:00 PM | May 24 (more info)

    • Location: Fowley Park, 106 Fowley Drive, Oakville

    • Description: Day-long celebration featuring Asian food, cultural showcases, and live performances

  • Spin & Sip Coffee Party 11:30 AM | May 24 (more info)

    • Location: Flyspin, 302 Lakeshore Road East, Oakville

    • Description: Join a pre-party spin class followed by a casual coffee social with friends in downtown Oakville

  • Plant Swap with Duran Place for Kids 1:00 PM - 3:00 PM | May 24 (more info)

    • Location: Knox Church, 89 Dunn Street, Oakville

    • Description: Free plant exchange featuring houseplants, seedlings, and garden swaps.

  • South Asian Heritage Month 3:00 PM - 10:00 PM | May 24 (more info)

    • Location: St. Volodymyr Cultural Centre, 1280 Dundas Street West, Oakville

    • Description: Cultural celebration featuring performances, vendor market, and South Asian cuisine.

  • SensoryLIS Art Class 10:00 AM - 12:00 PM | May 24 (more info)

    • Location: Joshua Farm Gallery, 1086 Burnhamthorpe Road East, Oakville

    • Description: Mindfulness-based art workshop exploring sensory experiences and mixed media.

  • Oakville's Spring Clothing Swap 10:30 AM - 2:00 PM | May 24 (more info)

    • Location: Walton Memorial United Church, 2489 Lakeshore Road West, Oakville

    • Description: Clothing swap event promoting sustainable fashion and community connection.

  • Northeast Oakville Fair 11:00 AM - 4:00 PM | May 25 (more info)

    • Location: Northeast Oakville Fair, 1051 Glenashton Drive, Oakville

    • Description: Community fair with inflatables, live music, and a sports zone.

  • Monday Coffee and Conversation Oakville 10:00 AM - 11:00 AM | May 26 (more info)

    • Location: The Women's Centre, 1515 Rebecca Street, Oakville

    • Description: Casual weekly coffee hour for women to connect, chat, and explore programs at the Women's Centre in a relaxed setting.

  • Women's Social Gathering 6:00 PM - 7:30 PM | May 26 (more info)

    • Location: The Women's Centre of Halton, 1515 Rebecca Street, Oakville

    • Description: Casual in-person meet-up with warm drinks, games, and conversation for women in a welcoming community setting.

  • Monday Night Trivia at The Tipsy Fox 7:30 PM - 9:00 PM | May 26 (more info)

    • Location: The Tipsy Fox Pub & Grill, 478 Dundas Street West, Oakville

    • Description: Weekly visual trivia game hosted on venue TVs with digital scoring and prizes. Free to play.

  • Halton Food for Thought Breakfast Bash 7:30 AM - 9:30 AM | May 27 (more info)

    • Location: Oakville Conference Centre, 2515 Wyecroft Road, Oakville

    • Description: Annual fundraiser supporting Halton student nutrition programs, featuring a breakfast marketplace, silent auction, and community celebration.

  • lululemon Oakville Lakeshore Run Club 6:30 PM - 7:30 PM | May 27 (more info)

    • Location: George's Square, Sumner Avenue and Reynolds Street, Oakville

    • Description: Weekly community run welcoming all fitness levels, hosted by lululemon Oakville Lakeshore.

  • Spring Stroller Socials 11:00 AM - 12:00 PM | May 28 (more info)

    • Location: Towne Square, 94 George Street, Oakville

    • Description: Join a guided stroller walk through Downtown Oakville, ending with coffee and social time for parents.

  • LeadTribes Oakville 12:15 PM | May 28 (more info)

    • Location: Milestones Restaurant, 3051 Vega Boulevard, Mississauga

    • Description: Weekly in-person networking event supporting Ontario entrepreneurs through leadership development and community connection.

  • Oakville Speed Dating 7:00 PM - 9:00 PM | May 28 (more info)

    • Location: Paradiso, 125 Lakeshore Road East, Oakville

    • Description: Meet up to 15 new singles in one evening of fast-paced, hosted speed dating.

  • Dance Essentials Class 6:30 PM - 7:30 PM | May 28 (more info)

    • Location: Taste of Colombia, 67 Bronte Road, Oakville

    • Description: Weekly movement class to improve flexibility, strength, and technique through ballet-based and conditioning exercises.

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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