Winnipeg Guides | Tourism Winnipeg

Dan Clapson, best-selling cookbook author and CTV's The Good Stuff's guest expert, on what to experience in The Peg

After visiting Winnipeg for well over a decade, I’m always a bit surprised at just how few Canadians have been to the city. It’s not that Winnipeg needs the validation of outsiders to know it's cool — because it certainly is, but I think it’s a real shame that people in other parts of Canada have no clue what they’re missing.

I try to not take it personally, because generally speaking, Canadians have a pretty bad track record at exploring their own country. This is one of the many reasons why I invited 26 of my closest friends –- from cities including Toronto; Halifax; London, England; Vancouver; Saskatchewan; etc… many of whom had never been here before –- to come celebrate my 40th in Winnipeg last year. The itinerary below is based off that whirlwind of a weekend, where the whole crew gave The Peg rave-reviews.

If you’re a fan of cities that have elements like, oh I don’t know, a booming and dynamic food scene, a thriving art community, a captivating history that goes back long before said city itself, cool architecture and amazing live music (just to name a few), then a weekend trip to Winnipeg sounds like something you might enjoy!

As a self-proclaimed unofficial Winnipegger, allow me to be your 48(ish)-hour tour guide to the Manitoba capital.

Friday

With an ever-growing number of direct flights, getting to Winnipeg has never been easier from within Canada, while there are also direct flights from several US cities including LA, Chicago, Atlanta and parts of Florida.

You’ve arrived, you’re all checked in at one of Winnipeg’s cool hotel properties (The Mere, Fort Garry Hotel and Inn at The Forks are personal favourites of mine), so best snag a coffee from a top-notch spot like Fools & Horses or Thom Bargen and get energized for a fun first day.

Lunch

While a hoagie’s time in the food trend limelight is fading, just know that Hoagie Boyz make this type of sandwich better than most across Canada — and were ahead of the curve to boot. Except no substitutions.

Explore

The Winnipeg Art Gallery (WAG-Qaumajuq) is famous for its striking art installations and rotating exhibitions, but the focal point of a visit here is the multi-level collection of Inuit stone carvings. It is absolutely incredible, the artistry and history is truly palpable when viewing.

Dinner

Winnipeg has no shortage of nationally recognized eateries, so for night one in the Manitoba capital I say set the tone with a place that’s especially acclaimed such as Mandel Hitzer’s deer + almond (the folks behind RAW: almond) or chef Emily Butcher’s Nola. Her European-Chinese fusion dishes are well worth enjoying.

Drinks

The funky, lower-level Sous Sol is also a reliable dinner recommendation, but I especially love this unconventional spot for casual late-night bites that segue into one-too-many dirty martinis. Are you in a dungeon or a grandma’s dining room? Questions to ask yourself while sipping.

For drinks, also check out Darling Bar in The Exchange. The lighting is *chef’s kiss* for a first date.

Saturday

Coffee and doughnuts

As mentioned, Winnipeg has plenty of top-notch coffee shops, but the one that started it all (or was at the beginning of the craft coffee shop movement) is Parlour. Pop in here for a cup of serious coffee before strolling down Main Street, hook a right and head to Oh Doughnuts. The imaginative doughnut shop is famous locally for their seasonal creations and signature treats, but it now offers breakfast dishes too, so savoury and sweet tooths can be equally satisfied.

Explore

Both an architectural stunner and a profound destination to absorb our country’s sorted past, the Canadian Museum for Human Rights needs to be experienced at least once (or twice) by every visitor. It’s hard to captivate a person with injustice exhibit after exhibit, but CMHR does it so beautifully and emotionally. It’s impossible to leave here not feeling affected.

Lunch

Get a taste of Winnipeg’s robust Vietnamese food scene at what I consider to be one of the city’s tastiest spots, Viva Restaurant. If you want to venture beyond pho (tasty), spring rolls (also very good) et al. then I would suggest ordering banh xeo here. It’s a fairly uncommon dish to find on a menu in the Prairies and here you’ll get a generous portion of it filled with prawns, pork and bean sprouts, so you shan’t leave here hungry.

If you’re craving a supremely indulgent burger then head to Dairi-Whip or VJ’s Drive-Inn to try a Fat Boy. This Winnipeg-style burger shares some similarities with a Toronto banquet burger, but ups the ante with meat sauce and thick spears of pickles. This burger is a sure-fire hangover cure, should you require such treatment!

Afternoon brewery tour

Winnipeg has one of the smallest craft beer scenes in the country, but it is small and mighty. Nonsuch Brewing boasts one of the most gorgeous taprooms in Canada, with quality brews to match, then there’s the queer-owned Good Neighbour Brewing (a rarity in the beer world) that has a welcoming charm all its own, and last, but not least, the ever-creative Low Life Barrel House continually churns out funky beers, ciders, and wines made with organic Ontario grapes. Who said  Winnipeg-made wine can’t be tasty?

Or take a break

Upon entry, the Scandinavian-style spa Thermea will transport you to a world away. The outdoor pools, the saunas, the aromatics… Being away from your cell phone has never felt so good.

Dinner

One would be foolish to not swing by  Canada’s oldest steakhouse when in Winnipeg. Rae & Jerry’s is a throwback like no other, complete with red leather lounge chairs and a side of tomato juice with, well, most things you order off the menu. Classic cocktails, classic table service, classic prawn cocktails…what more could you want from Canada’s O.G. steakhouse?

Drinks / live music

Times Changed is what I consider to be one of Canada’s only true honky tonks (take that, Alberta). You’ll always find amazing talent on the stage here, and even after the music dwindles, you’re still guaranteed an eclectic crowd and fun times until last call.

Sunday

Brunch

Getting to Clementine as early as possible is absolutely essential. Not only to minimize your wait time — yes, it does get that busy that early — but also to finally know what true brunch culinary bliss feels like. The restaurant is famous for many dishes, but if you see a burger on the menu, consider whatever iteration it may be a must-order. Then there’s the fried chicken, Turkish eggs (healthy-ish at its best!), and the yogurt panna cotta is not to be missed. A sneaky, sweet treat to wrap up a meal here.

Lunch

It’s almost time to head to the airport, so let’s do better than two-birds-with-one-stone and head to The Common/The Forks Market where there’s a plethora if interesting food vendors at your disposable, plus a satellite location of independent bookstore McNally Robinson, and much, much more. BASTA! Is easily a standout in this ever-buzzing food hall (Canada’s first contemporary food hall to be exact) for its playful take on classic Filipino dishes.

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If you have only one day, here's what Dan recommends, via CTV's The Good Stuff with Mary Berg. 

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Dan Clapson is the co-founder and creative director of Eat North and the Prairies food critic for The Globe and Mail. His work can be found in publications including Out Magazine, Air Canada enRoute, Eater, Vice, Calgary Herald, Xtra and more. Clapson’s debut cookbook Prairie was released in 2023 via Appetite by Random House.