Finding the lighter side of the Dark Side: Inaugural Dartmouth comedy festival searches for best local comic

Dartmouth’s inaugural City of Laughs comedy festival is bringing shows and events to downtown venues from Thursday to Sunday, including a contest that will send one talented local comic to the Edinburgh Festival Fringe.

“The focus is to give local comics an opportunity to perform and to win a great prize," says John Helmkay, City of Laughs’ producer. He says he wanted 18 comics for the competition but his colleagues thought he might struggle to find them.

“They say there’s only six good comics in Halifax,” Helmkay says. “Well bullsh*t, because I had almost 30 apply to be part of this festival."

Helmkay says almost all of the applicants are Halifax and Dartmouth based with a few coming from New Brunswick.

The winning comic will also receive the Mary Walsh award, named after the actress and comedian from St. John’s, best known for her work on This Hour has 22 Minutes and Codco. Walsh will open the festival finale show where the six City of Laughs finalists will go head-to-head before she presents one of them the award that bears her name.

“She’s been my good luck charm,” Helmkay says. “I don’t think she gets to appear as much in Halifax as she probably should. People want to see her.”

Fellow headliner John Wing, a veteran of The Tonight Show and the Just for Laughs festival, brings his show to the Sanctuary Arts Centre Friday night, and will emcee Sunday’s finale.

Helmkay says diversity has been one of the strengths of his shows since the first time he booked Walsh.

“She had one request,” he says. “Book at least 50 per cent female comics. At that time, like 20 years ago, it was rare.”

His shows have expanded to include other diverse communities since. In Dartmouth, that commitment includes an alcohol-free show at St. James Hall, in partnership with the Freedom Foundation, a recovery home for men.

Helmkay says he wanted to provide a safe space for sober audiences, and anyone who’d rather avoid obnoxious hecklers. He says it’s also an acknowledgement of addiction and mental health crises in comedy.

“It’s not hard to find comedians that have a link to mental health, right?” Helmkay says a lot of comics are quite open about their recovery, so it’s worth giving it space at a comedy festival.

Walsh and other seasoned comics will share the stage with regional up-and-comers looking for a break.

“There are some great comics that have come out of here and we want to see more,” Helmkay says. He expects local comedians will exceed expectations, but he says he also wants to give beginners stage time.

“Comics will all tell you, the only way to become a great standup is to fail on stage,” he says. “I wanted to have a fringe comedy festival feel. I want some people who are just starting, and sure, they may stumble.”

The festival is also a homecoming for Helmkay, who’s been producing the Crackup Comedy Festival in Ottawa and the Arctic Comedy Festival in Canada’s North for more than two decades. He grew up in Dartmouth and he says he wants to prove it’s a funny city and build a comedy pipeline for Canada by sending comics around the country to other festivals he’s created.

“I’m not doing anything with Americans until 2029,” he says. “Because of the way the administration treats Canada and Canadians.”

Helmkay says he doesn’t have time for the comedy culture wars but Canadian comics are having a harder time getting into the United States to work. He says he wants to create an annual festival centred on local comedy that attracts international talent. Dartmouth venues have signed on.

“I don’t know a lot about comedy,” says Imen Sendi, owner of The Beaver’s Den on Portland Street, one of the festival venues. “If it’s something that brings people together, why not?”

The focus is on giving local comics an opportunity to perform, says Helmkay, but they will be paid 25 per cent of door proceeds and there are cash prizes for finalists. Another 25 per cent goes to the festival’s charity partners with the remainder covering costs, but Helmkay says making money isn’t the point.

“It’s pay what you can, right? We’re not asking for a set ticket price.”

Tickets are available online to help with numbers, but Sendi says you can also pay by donation at the door. “You can come in and give whatever you want.”

Helmkay says they’ll accept people at each show until the room is full. The preliminary round begins Thursday night. The audience votes for six finalists over three nights of performances. Judges narrow it down to the final three, and then the audience picks the winner during the finale show Sunday night at the Sanctuary Arts Centre.

“It’s a small community here,” says Sendi. “If we do not support each other, we won’t have a community.”

Helmkay says Sendi might have to apologize to her neighbours.

“The laughter will be so loud the people in the condos will complain.”

Copyright 2026, South Dartmouth Post. All rights reserved.

Jeremy Hull, Local Journalism Initiative Reporter, South Dartmouth Post.