Canyon's publicist, Anya Wilson, says the singer was dropped off with his tour manager in Lloydminster on Saturday for a performance of "The Huron Carole" in the city that evening.
The pilot then took off for High River, south of Calgary, but the Cessna 210 slammed into the ground shortly after takeoff and slid into a house.
A person who was in the house wasn't hurt, but the pilot was killed.
Wilson says Canyon learned of the tragedy at about dinner time, not long before the show.
Transport Canada is investigating the cause of the crash.
"I have just lost a dear friend who was not just an aviation buddy, we shared an interest in sports and often played hockey together," Canyon, who lives in High River, said in a statement released Sunday.
"He and I have flown many times all over the place. I am devastated with the news and my prayers and thoughts are all with his family and friends."
RCMP have not released the pilot's name but say his family have been notified. Police and an official with the Transportation Safety Board both say the aircraft belonged to J.W.L. Engineering.
Wilson said the performance in Lloydminster went ahead on Saturday.
"It would have been very tough," she said.
She said he wasn't talking much on Sunday.
The Huron Carole is a concert series that supports organizations that work with the homeless and hungry in Canada.
Canyon will be performing "The Huron Carole" again in Calgary on Tuesday.
RCMP have said weather conditions at the time of the crash were poor.
Transportation Safety Board spokesman John Lee cautioned that different conditions could affect pilots and planes in different ways, and might not necessarily contribute to a crash.
Lee noted, however, that there was light and drifting snow at the time and visibility was about a kilometre and a half, with a cloud ceiling of 600 metres. Winds were 25 to 35 kilometres per hour and the temperature was —19 C, he said.
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