Forty Years on the Island: The John Leacock Family Story

Hillside Festival is the sum of the people who are committed to making it happen. It’s this piece that has allowed Hillside to grow and evolve to what it is today, much like the people who have helped shape Hillside have grown over generations.

From a Food Booth to the Boardroom

John Leacock first came to Hillside in 1994 as a food vendor, running a Caribbean booth with his friends, serving curry chicken, mango juice, and flavours rooted in Trinidad and Tobago. 

This quickly transformed into nearly a decade of involvement and dedication to the festival. In 1998, John was working with the radio at the University of Guelph’s campus station, helping promote music and build relationships that fed directly into the festival’s growth. He had joined the festival’s board of directors at a time when the young festival was struggling financially, carrying debt and facing an uncertain future. Despite this, John believed strongly in the future of the festival, in the artists, the community, and the idea that a festival like Hillside could exist and succeed.

Growing the Festival Without Losing It

By the early 2000s, Hillside had momentum, but growth came with pressure. How would they grow the festival without it losing its true values? How do you sustain a non-profit without handing it over to corporate influence?

The answer for Hillside was moving with intention and dedication to its values. Local and international artists would share the same stage. Jam sessions and collaborations were encouraged over big polished performances. A willingness to introduce audiences to music they didn’t already know. 

John’s own background helped shape that direction, bringing Caribbean influences and global perspectives to the festival through artists, programming, and cultural exchange. 

By the mid-2000s, Hillside was selling out. It never became a “Mega Festival,” and that was what made it so unique. 

A Life Built Around the Festival

Hillside is woven into the fabric of John’s life in many ways. His kids grew up there. Running through the festival grounds, covered in mud. Moving freely between spaces and people in a way that always felt safe and familiar. 

It reminded him of home. Growing up in the Caribbean, the community was something you could trust. It was a place where people helped and looked out for each other, and where music and arts were an important part of the culture and community. 

His children grew up and went from exploring the festival to performing in it. John remembers his son, at just nine years old, carrying a big Djembe drum onto the bus alone, making the trip to the main stage where he would open up the festival. 

Later, his son would go on to play drums professionally. The festival shaped their childhood and stayed with them for years to come.

Taking Hillside Beyond Guelph

Inspired by the festival model, John helped bring those same values to Tobago by launching the Tobago Jazz Festival, a festival rooted in the same principles of community, collaboration and cultural exchange. From island to island, the same values and spirit ring true, proving that what Hillside stands for lives wherever people choose to create it. 

The Moment That Stays With Him

For all of John’s years with the festival, the roles, the milestones, the headliners, what stands out most for him is the moment when the festival opens every year.

He recalls standing in the crowd on Friday at the Indigenous circle for the acknowledgement and lighting of the fire. Thousands of people around, all coming from different backgrounds and lives, in the same place for the same reason. 

The music, the food, the people, the atmosphere, it all comes together at once and then, just as quickly as it came together, it’s gone. That’s the piece John describes that stays with him, the moments shared. 

Why Choose Hillside

John has seen Hillside from every angle: a vendor, a volunteer, a board member, and a parent. 

Through all of it, one thing that hasn’t changed is what the festival gives back to its people. 

A place where kids grow up surrounded by culture and creativity, somewhere to explore and try new things, a place where community isn’t a buzzword but the heart of what makes Hillside so special. 

In our current time, where everything feels faster, more commercial, louder and bigger. Hillside offers something rare. It gives you something back. A feeling you forgot you were missing, and that’s why people keep choosing it. Places like this don’t survive by accident; they survive because people decide they matter.

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Share Your Hillside Story

For over four decades, Hillside has been shaped by the people who return year after year – families, friends, volunteers, artists, and music lovers who have made Hillside part of their story.

Now we want to hear yours.

To celebration the launch of our #MyHillsideStory community campaign, we’re giving on lucky winner 2 weekend passes to Hillside Festival!

Entering is easy – just follow the step on your preferred platform:

Whether it’s your first festival memory or a tradition decades in the making, we can’t wait to celebrate the stories that make Hillside feel like home.