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She finds the sky’s the limit

In high school, Heather Gregory stood out from the crowd. She pierced her nose, wore black combat boots and a studded collar, and spiked her blue hair into a six-inch mohawk. Her former classmates would hardly recognize her now, in a neat white shirt with a dark tie and epaulets, her blond hair tucked under a headset.

Gregory, 24, is a commercial pilot flying out of Thompson, Manitoba with Perimeter Aviation. Last week she returned home to St. Jacobs for a short visit with her family.

Former EDSS student Heather Gregory holds up her pilot’s license. Gregory flies out of Thompson, Manitoba for Perimeter Aviation.
Former EDSS student Heather Gregory holds up her pilot’s license. Gregory flies out of Thompson, Manitoba for Perimeter Aviation.

Gregory has loved flying since she was a little girl going on family trips, but she didn’t always want to be a pilot.

“I wanted to be an archaeologist, computer graphics designer, fashion designer, all kinds of different stuff,” she said. “When you wish for stuff when you blow out your candles, I always wished to fly, but not as a pilot. I didn’t think I could do that. It didn’t dawn on me that you could.”

It was her dad, Ken, who got her thinking about sitting in the pilot’s seat. He had always wanted to be a pilot, and for her 18th birthday he bought her a certificate for a flight at what was then the Waterloo Regional Airport. An instructor handled the takeoff, then let her take the controls. Gregory loved it.

“When you get up there and you’ve got that freedom, it’s just amazing,” she said.

With her dad’s help, she enrolled in flying lessons and washed airplanes to help pay for them. She dyed her hair blond and wore it parted down the middle to hide the shaved sides of her head.

Even though she loved being in the air and toyed with the idea of getting her private license, Gregory still wasn’t thinking of flying as a career. It wasn’t until she was finishing her last semester of classes that she discovered Conestoga College had an aviation program.

Gregory was one of two girls in her class of 20. There aren’t many female pilots, and Gregory said her parents are proud of her for doing something a little different. She credits her parents, especially her dad, with supporting and encouraging her down a solid career path.

“I wasn’t doing badly in school or anything, I just didn’t know where I wanted to go and could have gone a lot of bad directions,” she said. “If it wasn’t for [my dad], I wouldn’t have gotten to do any of it. … Hopefully I can get on with Air Canada and pay him back with flights.”

After graduating, she worked for Adler Aviation, doing everything from dispatch to charter quotes to washing airplanes. The only thing she didn’t do was fly for the company. Disappointed, she quit after six months. On the advice of an Air Canada pilot (a fellow member of Canadian Women in Aviation) she took her dad’s camper van and toured across Ontario, handing out resumes and applying for jobs.

She didn’t have much luck in northern Ontario – most companies do a lot of float landings and she didn’t have her float rating – and finally ended up in Winnipeg.

Former classmates told her not to bother applying at Perimeter, but Gregory didn’t listen and is glad she didn’t.

“I walked in there and I immediately met the chief pilot, got a tour, came back for an interview, and they hired me. [They] told me to go home, get my stuff and come back and they’d put me in whichever department needed me.”

That department ended up being stores, where she was responsible for handing out tools to the mechanics. After a year on the ground, they offered her a spot flying out of Thompson. Gregory jumped at the chance to get up in the air.

Thompson is a small city of 13,000 about 740 kilometres north of Winnipeg. Perimeter serves the scattered First Nations reserves in northern Manitoba, flying people in and out of Thompson and delivering supplies to the reserves.

On the reserve, a four-litre jug of milk costs $18. Because the cost of flights is subsidized by the government, it’s cheaper to fly into Thompson and buy supplies there, and then fly back.

Gregory’s favourite part of flying up north is the terrain; they’re allowed to fly 500 feet above ground, and she’s seen caribou, bears, and what she thought was a wolf.

She’s also had some less captivating experiences; in Lac Brochet, she and another female pilot got stuck in the sand when the turnaround base on the edge of the lake wasn’t properly packed. They had to make the passengers stand along the side of the runway for an hour and a half while they used a tractor to pull the plane out.

Gregory plans to spend another two and a half years in Thompson; she wants to get upgraded to captain and build up hours flying as a captain before moving on to a bigger airline like Jazz or Air Canada. She would like to come back to this area to be closer to her family, but like a good pilot, she’s open to going anywhere.

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