Every summer, Kingston comes to life during the festival season. Annual favourites like Skeleton Park Arts Festival, Back to the Farm, Wolfe Island Music Festival and YGK Craft Beer Fest pull in a mix of local and touring artists and fill the city with activity. 

But one festival has been missing from the mix for the last few years.

In 2023, the Downtown Kingston BIA hosted its final Limestone City Blues Festival, closing out its 26-year run. Though there’s been no shortage of music in town since, and Kingston Blues Society has carried on the festival at a smaller scale, the festival's absence has left a void in the scene. 

However, this year, a true successor has arrived.

Different Festival, Different Experience

This September, Downtown Kingston will fill that void with the inaugural RoadTrip Music Festival, a single-day festival featuring live performance stages across Princess Street and Springer Market Square. Details and advance tickets here.

It may sound familiar, but one look at the lineup and you’ll notice something special: The artists span a variety of genres, from pop and rock to R&B and country, pairing local favourites like Kasador and Tiny Horse alongside established artists like Peach Pit and Gabriel Jacoby. It’s a unique lineup, one inspired by careful curation, and that’s no coincidence. 

It’s because Downtown Kingston tapped Kingston's Virginia Clark and Steve Jordan to materialize their vision for an urban music festival unlike any other.

Building Off Local Cred

Steve Jordan has worn many hats over the years in the Canadian music industry. In past lives he’s worked in positions ranging from broadcast radio and small record labels to music management. In 2006, he started the Polaris Music Prize, an annual juried contest awarding $30,000 to a band or artist for Canadian Album of the Year. So when Downtown Kingston was looking for someone who could guide the development of their new festival, Steve was a no-brainer. 

RoadTrip isn’t Steve’s first time working in Kingston. His connection with the city actually goes back many years.

“I grew up in Kingston. I worked at CKLC, a legendary radio station,” Steve explained. “I started working there when I was 15. I was in my last year of high school, dragging my ass to class at 9 after doing the midnight to 6 shift… And I was sort of at the second wave of Kingston bands. The Hip were just starting. A couple of guys at 13 Engines were from Kingston. Sarah Harmer, in her first band The Saddletramps, would come through.”

Even in high school, Steve had an astute ear for talent. He was one of the first to play The Tragically Hip around the time of their self-titled EP. It’s that ear that helped carve his path through the music industry.

“I started as a promo and publicity person, so trying to get songs on the radio for our artists and trying to get media coverage, but really A and R (artist and repertoire) was what I ended up doing by default,” said Steve. “It was just more about finding, developing talent, recording them. In my case, even commissioning music videos as well, too. So I did that for Kinetic and then a job came open at Warner Music for A and R. I ended up getting that, and so I was doing major label A and R for a few years.”

Making the Kingston Connections

Steve’s years of experience in the Canadian music industry, especially working with emerging artists, made him an ideal pick to help build a new music festival in Kingston. That’s where local live music promoter extraordinaire Virginia Clark enters the picture.

The founder of Flying V Productions, Virginia has been a driving force within the Kingston music scene for over two decades. She was working with Downtown Kingston on designing RoadTrip when she gave Steve the call.

“[Virginia] told me that [Downtown Kingston] were thinking of doing this. I was kind of between projects at the time and I said, 'Well, I don't want to step in on your relationship, but I have time on my hands if you want to try and help build something to guide their choices.' So we did a little bit of market research for them just to talk to other festivals about best practices on timing and experience and timeline and curation and all of these things. And I think it was all stuff we kind of already felt and knew, but it's good to have it confirmed by other more successful festivals.”

Designing an Unforgettable Lineup

Before long, Steve and Virginia got to work on curation with a specific goal in mind: variety. 

“[Virginia and I] don't believe (as others in a mass market situation might believe) that people's tastes are narrow. We think they're quite broad, and we think they're quite open to hearing a soul, rap, hip-hop artist like [Gabriel] Jacoby next to a rock-pop artist like Peach Pit next to Katie Tupper, who is basically like this sultry soul presence,” Steve described.

Other acts performing at RoadTrip Music Festival include Toronto pop-R&B duo Absolute Treat, 2026 SOCAN Polaris Song Prize Long Lister Mariel Buckley, and local acts Piner and O Green.

“You do want people to walk away going ‘That was time well spent.’ We have such a fire hose of options to spend our time. We can't handle it all. We need people to curate who might share your taste or your sense of adventure or your sense of curiosity.”

For the full interview, check out the August 2026 episode of the Kingston Live podcast (to be released August 1, 2026). 

The inaugural RoadTrip Music Festival takes place September 12, 2026 throughout Kingston's downtown. Details including the full lineup and schedule and links to purchase advance tickets here.