Perhaps like all Canadian children, in my youth I was a dedicated fan of Winnie the Pooh. Tigger was something of an inspiration to me, so I bounced off the walls, much to the chagrin of my parents and teachers. I learned early on that A.A Milne’s character, “Winnie,” was actually based on a real female black bear named “Winnipeg” (nicknamed “Winnie” for short) who was rescued by a cavalry veterinarian in the First World War.

I think that’s when my fascination with visiting Winnipeg began. I wasn’t necessarily concerned with all the fun things to do in Winnipeg or anything of that nature, but, somewhere in my innocent youthful heart, I thought I might find Tigger.

On a cross-country train trip around the age of 12, we stopped in Winnipeg just for a few hours. Winnie the Pooh was a bit of an afterthought at that point, but that trip was the moment I feel that my travel heart began beating in this life. I didn’t have time to experience all the Winnipeg attractions, or even wander too far away from The Forks, but I remember pulling out of the station and vowing that one day I’d return.

And, nearly twenty years later, that’s exactly what I did.

Winnipeg, as you might imagine, has changed a great deal in that time, as have I. Despite all the anticipation and build-up that I felt in returning after all these years, Winnipeg did not disappoint. I found a lot of pockets and places to visit in Winnipeg that I really jived with, and I thought I ought to share them with you, like any good travel blogger should.

What Are the Best Things to do in Winnipeg When You Visit?

Winnipeg is, in my opinion, regularly underestimated, but let’s not forget that in terms of Canadian cities, only six are bigger than Winnipeg (in order - Toronto, Montreal, Vancouver, Calgary, Edmonton, Ottawa). It is, in a variety of ways, a quintessential cultural hub of the Prairies, central Canada, and the nation at large.

I’ve never been a writer who is comfortable painting an endlessly rosy picture without some counterbalance, so, sure, Winnipeg has had its difficulties in the past, and still has some difficulties in the present. But, too often, not unlike Cleveland, I’ve seen a tendency for people to form their opinions from afar without ever coming here to see for themselves what Winnipeg is all about.

So that’s what this post is about for me. Urging you to come see for yourself what kind of city Winnipeg is, and my gut feeling is that, ideally with the aid of this article, you might just like what you find. I know I did .

Alright, let’s talk about what to do in Winnipeg if you’re headed there!

NOTE: This post may contain some affiliate links. That means, simply, that I may get commissions from some of my recommendations. That being said, my opinions are fully my own.

The Canadian Museum for Human Rights