What began as a dock party 14 years ago has now become one of the top Canadian music festivals.

Wolfe Island Music Festival (WIMF) has hosted an eclectic mix of great Canadian musicians — from Sam Roberts to Stars and from former Queen’s student Jill Barber to this year’s headliner Joel Plaskett.

Despite a busy festival season for next month’s line up, we chatted with a few performers about outdoor festivals, the Kingston art scene, potential memoirs and the nostalgia of returning to the Limestone City.

Joel Plaskett, frontman of the Emergency, works with his head down.

But while his head has been down, his career has been soaring upwards. He’s headlined shows across the globe and was handpicked to be the opening act for Paul McCartney’s Halifax concert in 2009.

“Every once in a while I look up and go ‘hey, there’s cool stuff happening’ and then I think [about] the fact that we’re able to come and headline a festival like Wolfe Island,” he said.

“[It’s] a testament to the fact that we’ve worked hard as a band.”

As someone very connected to his Canadian roots, Plaskett gets nostalgic when reminiscing about time spent in Kingston.

“I remember sitting on the porch of [WIMF artistic director and co-founder Virginia Clark]’s house singing songs with Jill Barber the last time I was there, on the way back from making my record La Dee Da,” he said. “Now that it’s all coming back to me, I’m picturing myself there.”

Kingston is an audience that is continuously growing and changing, he said. It reminds him of Halifax — though it’s in Ontario, Kingston’s a small slice of his Nova Scotia home.

“I really feel like it’s always been a huge supportive city for us and the band,” Plaskett said. “So we just keep coming back because it sort of has yet to let us down.”

Plaskett said he prefers to take his opportunities as they come, rather than planning for success.

“If you expect one thing to lead you to another, often you run the risk of being disappointed,” he said.

You have to find success in the moment, Plaskett said, and not in a tentative, unsure future.

Part of his great success is his ability to engage the crowd and tell meaningful stories.

It’s not just about expression, but also about entertainment.

“The idea of communicating something to people and getting something back is really important,” Plaskett said. “I like getting up and putting on a show, whether that’s dancing or talking or telling stories or having a laugh.”

Despite being a part of a variety of bands since the ‘90s, Emergency, comprised of Plaskett, Dave Marsh and Tim Brennan, has been the longest standing.

However, he likes to dabble between performing shows with his band, performing solo and a combination of the two. He doesn’t want to be cast as one or the other.

“The transition has always been pretty natural,” he said. “When I’m playing solo, it becomes a little bit more introspective and the story telling becomes a bigger part of the show.”

As an avid storyteller and thoughtful writer, Plaskett joked about one day writing a memoir.

“Maybe when I’m 50 or 60 and have 40 years on the road then I’ll have a few tall tales to tell,” Plaskett said.

He sings about the Cabot Trail in Cape Breton and has a twang in his voice that’s uniquely born from the East Coast. Qualities like these are what have won him countless East Coast Music Awards, Juno nominations and admiration from Canadian music enthusiasts here and abroad.

Wherever he goes, Plaskett said Canadians seem to pop out of the woodwork. As such, he likes to celebrate home with his music.

“I feel a real connection to where I’m from,” he said. “I’ve been here my whole life; I’ve never lived anywhere else.”

Joel Plaskett Emergency will be performing on Aug. 10 at 9:45 p.m.

He’s a full-time Ruffian, occasional solo artist and now a model. Born Ruffians frontman, Luke Lalonde, seems to do it all and more.

Lalonde, who played with the band at WIMF before, said the small size and unique location create the desirable atmosphere that’s bringing them back this year.

“I like playing [outdoor festivals] because it’s different than just showing up [and] playing a show at a club or regular venue,” Lalonde said. “There’s more of an atmosphere.”

The Toronto-based band formed in the early 2000s, joining together Lalonde, Mitch DeRosier, Steve Hamelin and, more recently, Andy Lloyd. They released their first full-length album, Red, Yellow & Blue, in 2008 and two others since then.

With their latest record Birthmarks released earlier this year, it’s easy to notice a slight shift in their sound.

“It’s mostly just changed in [us] becoming more interested in other sounds, listening to other kinds of music that generally shape and create who you are as a person,” he said.

Lalonde said he listened to a lot of electronic when creating Birthmarks. David Bowie, Talking Heads and James Holden were some influences.

The musician has been expanding his craft lately, dabbling in production and even releasing his debut solo album, Rythymnals.

Following his interest in production, Lalonde brought his technical experience to the table with his solo album and the Ruffians’ Birthmarks.

“Technically I’ve gotten more interested in production, like what I want in the studio, and more interested in using the studio as an instrument,” he said.

Lalonde said he completed Rythymnals, released last year, largely by himself.

“I started to accumulate songs that I basically just wanted to finish on my own,” he said.

A musician and a producer, it’s not surprising his resume now also includes modeling. He landed a spot in H&M’s spring catalogue this year. And if that’s not enough, the Ruffians begin their European tour in September.

But first, Lalonde and the band will hit Wolfe Island.

When asked what the audience should expect from the Ruffians at the festival, the multi-talent hesitated a bit.

“I don’t know,” he said. “Music?”

The Born Ruffians will be performing on Aug. 10 at 8:30 p.m.

Perhaps a testament to his prairie upbringing, Gavin Gardiner, lead singer of The Wooden Sky, gives off a sense of sincere humility when it comes to the band’s work.

Beyond the passion and the acknowledgment, Gardiner attributes his love for shows to simply enjoying himself.

“There’s something very conducive about the environment to having a good time,” Gardiner said. “The fact that it’s on an island makes it completely different and really special.”

He grew up in Morden, Manitoba and moved to Toronto to attend Ryerson University After meeting other musicians in the city, Gardiner formed a band which is now made of himself, Andrew Wyatt, Simon Walker, Andrew Kekewich and Edwin Huizinga.

They released their first LP, When Lost at Sea, in 2008 and never looked back.

The group has toured Kingston several times and described Brian’s Record Option and the farmer’s market as some of their local favourites. They’re returning to WIMF this year, after their last island performance in 2011.

When it comes to playing festivals, Gardiner gushed over the special moments that he and the audience get to experience during a show. When the atmosphere is bountiful with different artists, he said cool collaborations occur.

Gardiner recalls a moment at this past Toronto Urban Roots Festival (TURF).

He was in the audience watching Canadian band The Sadies perform when Kurt Vile, an American musician best known for his work with the band The War on Drugs, jumped onstage.

“I know for me, when I’m in the audience, [and] a singer from another band jumps up on stage with my favourite band and just sings along … it creates some kind of a special moment,” he said.

These kinds of happenings, for Gardiner, are what make a show unique, whether he’s performing or just watching.

“It’s easy to forget when you’re playing 200 shows in a year, how special those moments are for the audience,” he said.

Gardiner said he has a newfound appreciation for using music as a form of expression, though it can be cliché.

“I don’t necessarily deal with those emotions and things in my life,” he said. “Music allows me a way to do that.”

The Wooden Sky will be performing on Aug. 10 at 6 p.m.