Forty Years on the Island: The Taylor Family Story

For Andrew and Dylan Taylor, the Hillside Festival is a weekend in July that has become a thread connecting their family over three decades. 

Andrew and his wife, Noella, first came to Hillside in 1993. Andrew still has the t-shirt.  

At the time, Andrew and Noella had just moved back to Guelph, and they were looking for a way to reconnect with the community. What they found instead was something harder to define: a place that felt like the world working the way it should.

A few years later, Andrew and Noella’s son Dylan would join the family at the festival. New to the world and wrapped in a blanket on the grass, he was surrounded by his dad’s feet, placed around him to keep him safe. Hillside became a part of Dylan’s life before he could even remember it.  Two years later, Maddy was born and joined the family at Hillside.

Crossing Into Another World

Ask anyone who’s been, and they’ll tell you that the magic of Hillside starts as you turn the corner down the road in Guelph Lake Conservation to see the big “ANTICIPATION” sign. Further down the road, as you walk across the land bridge to Guelph Lake Island, you step into a new world. 

“Crossing onto the island feels like stepping into something slightly surreal, like passing through a quiet threshold where the usual rules don’t apply.” For Dylan, it’s always felt like a “going through the looking glass” moment. 

On the island, things shift. The chaos and busyness of the outside world go quiet. People are more open, more patient, and more willing to help strangers around them. And when the early summer weather calls for rain, festival goers are eager to help strangers push their cars out of the mud.

The Magic Isn’t Perfect, and That’s the Point

Some of the most memorable moments at Hillside are messy.

Rain turns the field grounds into a slip and slide. Power cuts out mid-set. Cars get stuck in parking lots, and shoes are lost in giant puddles of mud. 

And somehow, no one is angry or impatient. Instead, people show up for each other. 

Strangers direct traffic and band together to push cars free. Everyone’s soaked, covered head to toe in mud, and still laughing together. 

The festival is a live demonstration of what community can actually look like when people choose it. 

Music You Didn’t Know You Needed

At most festivals, the lineup is the deciding factor in buying tickets. Hillside offers a different experience: a weekend of discovery. 

Hillside goers trust the music curation and their ears to guide them to a new sound they will love. Often hidden in the schedule lineup is a band you have not yet heard of, one that will stay with you for years to come. 

For Dylan, this musical exploration changed how he thought about music. He discovered his next favourite band, and he watched sets that felt less like performances and more like a shared experience between the band and the audience. He watched artists at a grassroots level, and at 11 years old, something clicked. “I could do that.” That inspiration transformed into a later career in the music industry. 

That kind of discovery is rare now in a world where the algorithm serves you what you already like. Hillside does the opposite; it asks you to listen with curiosity.

A Festival That Grows With You and Stays With You

As a child, Hillside is all about the interactive art and music pieces, trying new foods, wandering, exploring, and making new friends. 

As you grow, Hillside offers something else. A safe place to explore your identity, music to express yourself, and the feeling of independence in a safe community. It becomes a place you long to return to, and you bring your family and friends to share the experience. 

Finding ways to stay connected across generations isn’t easy. Relationships change, life moves fast, and your priorities shift. For father and son, their connection through Hillside gave them something to hold onto. Hillside has been that constant. Something that the two have always shared, looked forward to and bonded over.

No How To Hillside Guide

Despite decades of stories, there’s still no official “How to Hillside.” No checklist for the festival, no perfect plan, and that’s the point. 

If you’re looking for it, there’s a place for you waiting at Hillside. 

An open embrace, a weekend to discover, where people show up for each other, where music feels alive through the beat of drums and feet jumping up and down under the tent of the stage.

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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 these steps 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.