What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com
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Our Canadian Adventure: What to eat in Calgary, Regina, and Winnipeg

The best places to eat and drink in Calgary, Regina, and Winnipeg

We’re driving across Canada and you can too, sort of – follow along as we go to Banff, the Canadian Badlands, and now Calgary, Regina, and Winnipeg!

In Canada, the cities in between Vancouver and Toronto don’t tend to get a lot of love. They don’t have the cool factor of Chicago, Austin, or SLC. Heck, they aren’t even seen to be as cool as Omaha. Omaha is cool. If you’ve ever talked to a Canadian, you’ve probably heard “Calgary? Just wishes it were as cool as Omaha”.

But these cities should not sell themselves short. They are pretty damn cool, and on a long road trip such as ours, a welcome respite from cold wet tents, bears, and a very obvious lack of laundry services.

Plus, cities have steak. And mixed drinks*.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

Since there is only one highway in Canada (basically) it hits up pretty much every major city except Saskatoon. We’re visiting everything on the way, and if you drive across Canada, you will probably end up making these exact same stops. We drove from Vancouver straight to Banff, and from there, we’ve paused at Calgary, Regina, and Winnipeg so far, plus a handful of small towns like Canmore and Moose Jaw that we stopped at to get coffee, because Steph is addicted to coffee.

Calgary was our first major stop. For me, Calgary was mainly the host city for the 1993 movie Cool Runnings starring John Candy. But it turns out, Calgary is far more than that, if you can believe that anything can outshine Cool Runnings.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

The entire province of Alberta is cattle country. It’s gorgeous and grassy and big sky’ed, and one day I dream of us owning an architectually inappropriate for the area modern wood and glass ranch house overlooking acres and acres of plains. So, suitably, our first stop in Calgary was Modern Steak. They do the know-your-farmer thing so much that they have their own cows situated at local farms which they assured us were very happy cows. Steph was excited to go because they had a Tomahawk steak, because even though she is tiny and eats accordingly, she thinks she is capable of finishing half of a 48oz+ steak. Spoiler alert: she wasn’t.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

The photo is outdoors because all steakhouses are dark as hell, and while the waiter was good natured about us taking a steak outdoors to photograph it, he insisted on carrying it because he thought she would drop it. The steak was perfect – beefy, texturally interesting (it had fatty parts, beefy parts, and sinewy parts to keep you interested) and it was humongous. Unfortunately, it comes with a price to match. I’m not sure I’d ever order it again, but I’m glad we tried it and there is something definitely fun about knowing that there is more high dollar steak on the table than you can conceivably eat.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

In the early days of our relationship, Steph would plan and plot our vacations out weeks in advance. Somehow these days that duty has gone to me and that means googling something like “Eater Heatmap for X” the night before we arrive. That tactic doesn’t work so well when you’re camping far away from LTE, and it certainly doesn’t work for cities that Eater doesn’t know of.

We ended up in Regina with nothing more than a hotel reservation and loads of daylight. I came across something called Regina style pizza so we decided to try it. Non-hyperbolically speaking, we were totally, absolutely blown away. It’s indescribable, it looks terrible, and I would drive the almost-exactly 1000 miles from the west coast again to get another slice. There is no photo because it would ruin the experience.

Imagine Chicago style deep dish pizza but instead of sauce, it was all your meaty and mushroomy toppings of choice. A pizza shaped lasagna with layers of toppings. It’s not really possible for me to describe this in an appealing way, though I’m sure Steph could, but it was bomb. The pizza place we went to (named best pizza in Canada by Food Network) is ironically named Houston Pizza. Why? No idea. They should have called it “Italians ain’t got nothing on this Pizza”.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

We found some pro tips online on how to get the best Regina pizza experience: order the all dressed – aka deluxe – and keep it under 10” or you won’t be able to pick it up. It said nothing about portion sizes so we ordered two smalls. The dude over the phone told me it came to about $30, which I thought was oddly high for a small town in Saskatchewan. That is until we picked up the boxes and realized we had ordered about 5lbs worth of pizza. Regina pizza is dense, and the two small 8 inchers were enough to feed us that night and all the next day.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

Known as the Peg, the last city on our list punches above its weight on everything from food to music. Winnipeg is the cultural heavy hitter of the three. Neil Young came from there. Crash Test Dummies came from there. Food-wise, we went to Deer + Almond and had some fantastic inspired food that would compete right up there with LA and NYC, served on local pottery that was made across the street. How awesome is that? We also went to no fewer than 3 breweries during our short stay there.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

On beer: Before IPAs were cool, you could only get Bud Light with Lime (which, granted, I love) between the coasts. Now that IPAs are ubiquitous, most beer geeks are looking for something different, like sours and goses. Just like with IPAs about 10 years ago, you won’t find anything outside of the big cool cities. Unless that is, you are in Winnipeg, where everyone is making gose-saisons and other weird beer geek blends. Winnipeg is a good place to be if you like drinking.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

On coffee: remember that coffee addiction thing? In every city we go to Steph insists on coffee, so in Winnipeg we ended up at a really cool third wave place called Fools and Horses, where along with awesome coffee they also serve beer! and doughnuts! This led to a doughnut discussion between me and Steph. You would think having been married for as long as we have that there would be nothing new to talk about, but it could not be further from the truth – Steph did not know that I used to be a donut addict and that my favorite donut flavor was unglazed. In fact, she did not know that you could get a donut unglazed.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

We discovered that these particularly great doughnuts came from a place down the street called Oh Doughnuts and decided to drive right on over there. They were sold out at only 1pm in the afternoon, so we resolved to go visit the next morning as soon as we woke up and it did not disappoint. Not only did they have the flavor she wanted: everything bagel, but donut – which should have been called all-dressed in keeping with the Canadian theme – but they also had unglazed! I think I made Steph a believer, because as we *all* know, there is no better donut than a fresh, hot, unglazed.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

 

Places I’d come back to:

Modern Steak
Houston Pizza
Deer + Almond
Oh Doughnuts
Fools & Horses Coffee
One Great City Brewing Co.
Peg Beer Co.

And Calgary, Regina, and Winnipeg.

-Mike

* Side note, cities aren’t the only places to get cocktails on our trips: Steph makes really awesome bottle aged old fashioneds before we go camping.

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com

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9 Comments

  1. Terry says:

    It reminds me of my own trip when I moved from the West to the East! Alas, because I had time constrains, my trip was rushed and couldn’t enjoy it the same way you did.

    One major note that hurts me, though: You are giving no love to Edmonton! I understand it would be a major detour from Calgary but, giving credit to where it is due, Edmonton is the fifth largest city (by population) in Canada!

    1. Mike says:

      Steph is actually from Edmonton so we’ve been there a bunch of times. She said the same thing to me when reading the part about every major city except Saskatoon… “What about Edmonton?!” Any recs?

  2. Samantha says:

    Interesting pick for Calgary! We’ve got much better restaurants than Modern Steak!

    1. Mike says:

      We went to Pigeonhole too, but only for drinks, it didn’t seem fair to include it

  3. Melissa says:

    There are really some hidden gems in Winnipeg, despite what the majority of Ontarians would say! Also, please share the recipe for the Old Fashioned!

    1. Mike says:

      Winnipeg was pretty awesome. I would come back for sure.

  4. Missy says:

    I LOVE this guide. I STILL have not made my way up to Canada and it is definitely on my short list. I will definitely reference all of this when it comes time :) I love your guide style, I too write a food and travel blog ( http://www.behindtheplates.com) and have found that these guides help provide inspiration for those (food loving) travellers out there like us. Keep up the awesome work!

  5. JC says:

    Glad you made time out to visit our little city, Winnipeg! There’s so much to explore in Winnipeg. :) Oh Doughnuts is def the best; I like their Everything Bagel too. Maybe next time you guys are back in town, do give Stella’s, Clementine, Segovia’s, Peasant Cookery a visit.

  6. Shannyn says:

    Would LOVE that bottle-aged old fashioned recipe!

What to eat in Calgary, Regina, and Winnipeg - www.iamafoodblog.com