For the first time, there will be six women at the meeting in Niagara-on-the-Lake, Ont., representing about 85 per cent of the country's population. And at the head of the table will be Kathleen Wynne, who was sworn in as Ontario's first woman premier just six months ago.
It's more than a photo op for the history books, she said.
"I was just talking to a grandmother who was saying her granddaughter wants to be the prime minister," Wynne said in an interview.
"The fact is that it's very important that people see themselves represented and that 50 per cent of the population is sitting at the table, better represented. It's a very good thing."
It matters because it signals to the public that women are capable of holding high public office on equal footing with men, said Jane Arscott, a professor at Athabasca University who writes about women in politics.
"We haven't seen that before," she said. "It will shift in our minds our sensibility about who can lead and how they will do it."
But the appearance of gender equality can be deceiving, experts say. Even though six provinces and territories are led by women, female representation hasn't improved in the legislatures, said Christine de Clercy, a politics professor at the University of Western Ontario.
In fact, studies suggest that the gains made over the last 30 years have pretty much stopped, she said. The number of women in legislatures across Canada has reached a glass ceiling, she said.
"This might be a little bit of a historical hiccup we have: an unusual set of circumstances where we have lots of women premiers, but this is not some new harbinger of a better, more equal political environment," she said.
"In fact, it's just a quirk, and it might lead people to overestimate representation of women which ... in Canada, compared to many other countries, is still relatively poor."
Will this surge in female leadership change the dynamics among premiers? For Alberta Premier Alison Redford, it's more about the new faces than the female ones.
"I'm pretty excited about the Council of the Federation, not because we have so many new women leaders, but because we have so many new leaders," she said.
Some, like British Columbia Premier Christy Clark, have been given a new mandate to govern by winning a general election, Redford said.
"I think there's going to be incredible dynamism because we have passionate leaders around the table that have exciting visions for the future," she said.
It's difficult to say whether the new wave of female premiers will shift the tone of the talks, said Arscott.
"I would expect the discussion to be a little bit different in how the meeting is conducted, just because there may be more pauses for people to be able to express their opinions," she said.
Newfoundland and Labrador Premier Kathy Dunderdale said the dynamics have changed since her first meeting several years ago, when she and Nunavut Premier Eva Aariak were the only women in attendance.
"I can tell you that that COF meeting is very different from the COF meetings that we have now," she said. "And I'm sure that's due in large part to the changing players around the table."
Gender codes are still in play, dictating how women leaders are expected to behave, said Arscott.
"The media has a very large role in how that's reported, whether it's described in combative terms or in terms of decorum," she said. "It's not what occurs. It's the interpretation of it."
There simply aren't enough women who've reached the top of the political hierarchy to figure out what the overall effect will be, she said.
"They may be as mediocre as the men, but that's what equality brings us and that's fine," Arscott said. "We shouldn't expect that they have to do better or different in order to have the access to those resources and the benefits of holding those offices."
There may be more women, but there are other groups absent from the premiers' table, said De Clercy. Many pockets of society — including ethnic groups, aboriginal people and the disabled — are "hideously" under-represented in our political system.
"It's totally great that we have Premier Christy Clark, Premier Allison Redford, Premier Kathleen Wynne," she said.
"But when you think about it, these are the premiers of three of the most diverse provinces in the federation. And they're still from ... broadly Anglo-American, white, middle-class backgrounds."
— with files from Sue Bailie in St. John's, Nfld.
Note to readers: This is a corrected story. An earlier version misspelled Alberta Premier Alison Redford's name.