Oakville Community Events May 2026: Food Truck Friday & More

As we wrap up an incredible May, the community spirit in Oakville is reaching a high point. This week features some of the most anticipated events of the season, blending food, culture, and charity.

1. Food Truck Friday (May 29th)

One of our favorite local traditions returns this Friday! Community Living Oakville is hosting Food Truck Friday from 12 PM to 2 PM in the heart of Oakville Towne Square.

The Cause: This event celebrates Community Living Month, promoting diversity and inclusion.

The Food: Expect a variety of local favorites—it’s the perfect excuse to step out for a long lunch and support a fantastic non-profit that has served our region for over 70 years.

2. Oakville Psychic & Crystal Fair (May 29–31)

Looking for something a little more unique? The Psychic & Crystal Fair is happening at 475 North Service Road East all weekend. It’s a great way to explore the more eclectic side of our local community and perhaps find a unique piece of home decor.

3. Looking Ahead to June

The momentum doesn't stop here. With the Taste of Oakville Grand Tasting coming up in June and "Shop the Street" events on the horizon, the transition from spring to summer is the busiest time for our local BIAs.

Community Living in Oakville

A strong community is built on involvement. Whether you’re attending a fundraiser or just enjoying a meal in the Square, these moments are what make Oakville more than just a place to live—it's a place to belong.