Lt. Harry Colebourn, a Canadian veterinarian and soldier with the Royal Canadian Army Veterinary Corps, came across the orphaned female bear cub on Aug. 24, 1914.
"It's such a fascinating story to me that something from such a different, ancient time and far away is so directly connected to this city of ours," said Mary Anne Appleby, a Winnipeg author who penned the 2011 biography Winnie the Bear.
As the story goes, when Colebourn's troop train stopped in White River, Ont., he met a hunter who had shot and killed the bear cub's mother, without whom the cub was almost certain to die.
Colebourn offered the hunter $20 for the cub, whom he named Winnipeg Bear to commemorate the city where he had lived before the war. The name was soon shortened to Winnie.
Winnie accompanied Colebourn to England, where the cub played with Canadian soldiers during their off-hours in their encampment on the Salisbury Plains.
Colebourn later donated Winnie to the London Zoo, where the bear inspired the creation of A.A. Milne's famous children's book character. Winnie died at the zoo in 1934.
The Winnie the Pooh story endures a century later. A survey in the United Kingdom named Milne's book the most beloved children's book of the past 150 years, while the "silly old bear" came in second to Anne of Green Gables' Anne Shirley in CBC Books' Great Canadian Character Showdown.
Appleby, whose father was a close friend of Colebourn's son, says this weekend is a time to celebrate a wee bear that has become a household name.
"I just want to try and get this story out there as much as I can because I think, you know, in Winnipeg we're quite familiar with it. The rest of Canada doesn't know it as well," she said.
Appleby said in conducting her research, she came across a rare short video of Winnie eating an orange at the London Zoo.
Winnipeg's Assiniboine Park is home to the Pooh Gallery, which houses a permanent collection of Winnie the Pooh artifacts and memorabilia.
Featured prominently in the gallery is the painting Winnie the Pooh and the Honey Pot by E.H. Shepard, the original illustrator of Milne's series.
Prince Charles and his wife Camilla, the Duchess of Cornwall, viewed the painting during their visit to Winnipeg in May.
A bronze statue of Colebourn and Winnie is located at the park's Nature Playground.