Trudeau, 47, was already under fire for an ethics lapse and other controversies, so the resurfacing of photos and videos of him engaging in activities he himself termed "racist" dealt a fresh blow to his chances.
"I recognize that it is something absolutely unacceptable to do," Trudeau, who heads the Liberal Party, told a news conference during a campaign stop in Winnipeg.
"Darkening your face, regardless of the context or the circumstances, is always unacceptable because of the racist history of blackface," he said. "I should have understood that then and I never should have done it."
"The fact is that I didn't understand how hurtful this is to people who live with discrimination every single day. I have always acknowledged that I come from a place of privilege, but I now need to acknowledge that comes with a massive blind spot."
"And for that I am deeply sorry, and I apologize."
Canada's Trudeau admits to racist 'brownface' makeup
Earlier, broadcaster Global News released damning images of Trudeau in ripped jeans and a t-shirt, his arms up and wearing blackface makeup, which his campaign confirmed to AFP were taken "in the early 1990s."
This followed Time magazine's publishing on Wednesday of a photograph of him in dark makeup at an "Arabian Nights"-themed party 18 years ago.
The son of former prime minister Pierre Trudeau, who is considered the father of modern Canada, also admitted this week to wearing similar makeup in his teens when he sang Harry Belafonte's 1956 hit "Banana Boat Song (Day-O)" at a high school talent contest.
He acknowledged that these actions were "racist" and that his enthusiasm for costumes - which has also included dressing up as comic book hero Clark Kent/Superman and a "Star Wars" rebel pilot for Halloween - has not always been "appropriate."
Trudeau and the Liberals won a landslide victory in 2015, but are this year in a tight contest against the Conservatives led by Andrew Scheer.
Despite the political furor, Trudeau pressed on Thursday with campaign stops in Winnipeg and Saskatoon, ahead of the October 21 election.
US politicians have been mired in scandal in recent years when found to have worn blackface, which dates back to about 1830 and the tradition of so-called "minstrel shows."
In the shows, white performers caked their faces in greasepaint or shoe polish and drew on exaggerated lips in a caricature of blacks.
Hasan Minhaj 'tries' to convert Justin Trudeau to Islam in a hilarious video
The stereotypes portrayed - that blacks were somehow inferior, ignorant, lazy and even animalistic - cemented racist attitudes for decades. Some of those images still persist today.
Trudeau is a fervent advocate of multiculturalism integral to Canadian identity, and at least six members of his cabinet have Asian or African heritage.
But the scandal is sure to tarnish his golden boy image, already dented by accusations of political meddling in a bribery case against engineering giant SNC-Lavalin.
Green Party leader Elizabeth May called the Trudeau images "shameful" and urged him to "walk the talk" on progressivism, while Maxime Bernier, a former foreign minister who split with the Tories to form an upstart right-wing party, accused Trudeau of hypocrisy.
"He's the master of identity politics," Bernier said in a Twitter message, having "just spent months accusing everyone of being white supremacists."
Jagmeet Singh, an observant Sikh and leader of the third-place New Democrats, said the images showed a pattern of "deeply troubling" behavior by Trudeau.
"People who have faced injury both from physical violence and words, people who haven't been able to get jobs because of the color of their skin are waking up to see the prime minister of this country mock their lived realities," he said, "in not just one but multiple images."
"This is very painful for a lot of people."
Scheer, who has been Trudeau's most ardent critic, hammering him on ethics lapses, used the episode to once again call into question Trudeau's fitness and "moral authority to govern."
Wearing brownface or blackface, he said, "was just as racist in 2001 as it is in 2019."
He acknowledged also that the latest video of Trudeau was provided to the Conservative campaign, which passed it on to Global News.
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