Trunk Sale Event
In the years following COVID-19, small businesses and local entrepreneurs faced a shared problem: the audiences they'd built were hard to reach, trust was fragile, and the energy that comes from real, in-person community had been lost. Connectify Media partnered with Markham CommunityLink to create something that could bring it back.
The Trunk Sale Event was born from a simple idea — open up a parking lot, invite families to set up from their car trunks, bring in local sponsors, and let the community do what it does best: connect.
Each Trunk Sale brings together over 200 family booths where parents and children set up alongside each other to sell items, crafts, baked goods, and more. It's equal parts marketplace, community fair, and teaching moment — children get hands-on experience with commerce, pricing, selling, and customer interaction in a safe, fun environment.
Over 50+ local business sponsors participate in each event, gaining direct access to an engaged, family-oriented crowd that is genuinely receptive. It's the kind of community visibility that no digital ad can replicate — face-to-face, in the same neighbourhood, building real relationships.
Connectify Media handles the full event production lifecycle: venue logistics, sponsor coordination, vendor onboarding, on-site management, and post-event digital content to extend the reach of each edition.
Eight editions in, the Trunk Sale has become a staple of the Markham community calendar. Families return year after year. Sponsors report strong brand recall and genuine leads. And children who have participated for multiple years are growing up with a real, practical understanding of entrepreneurship.
The event has also served a larger purpose: since its first edition, the Trunk Sale has been a fundraiser for SickKids Hospital, raising over $9,000 across eight years — a testament to the generosity of the Markham community and the power of gathering people together for a shared cause.
Over 8 years, the Trunk Sale community has raised $9,000+ for the SickKids Foundation — one family, one booth, and one donation at a time.
View Thank You LetterA look inside the Trunk Sale experience.
We've done it 8 times. We know how to build events that people remember — and keep coming back to. Let's talk.
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