Winnipeg

Winnipeg

Jenna Rae Cakes

Class of note: Airport Food/Bakery
Name: Jenna Rae Cakes
Recommendation: Recommend
Date visited: 2026
Location: Winnipeg Richardson International Airport, Level 2, after security at Gate 9, serving domestic and international departures.
Note: Amazing macarons. If you’re looking to bring something home, this is the place.

Delta Hotel Winnipeg

Class of note: Hotel
Name: Delta Hotel Winnipeg
Recommendation: Highly Recommend
Date visited: Not specified
Note: The ‘IT hotel’ and best hotel in Winnipeg, but prices are getting out of control, sometimes reaching around $600 per night. You will run into other IT vendors staying here. It’s right next door to the conference center for events like the WCISC. Visiting NHL hockey teams also stay here when in town.

Elephant & Castle

Class of note: Restaurant
Name: Elephant & Castle
Recommendation: Recommend
Date visited: Not specified
Note: Located in the Delta. Great food.

529 Wellington

Class of note: Restaurant
Name: 529 Wellington
Recommendation: Highly Recommend
Date visited: Not specified
Note: Amazing. Get a private room. Amazing food, drinks and desserts. The Japanese A5 Wagyu is like candy in your mouth. Highly recommend.

529 Uptown

Class of note: Restaurant
Name: 529 Uptown
Recommendation: Do Not Recommend. Avoid.
Date visited: Not specified
Note: It’s in a hotel lobby, which is super odd, and the food is nothing like the 529 Willington. Do NOT recommend.

La Brasserie Nonsuch Brewing Co.

Class of note: Restaurant/Brewery
Name: La Brasserie Nonsuch Brewing Co.
Recommendation: Recommend
Date visited: 2025
Address: 125 Pacific Ave, Winnipeg, MB R3B 0M1
Note: They claim to make the best burger in the world, and it’s pretty damn good. Great for a beer, a meal or a work event.

Derran Guinan
Field CTO · Americas

Field CTO for the Americas at Veeam. 30+ years in IT and cybersecurity. I write about data protection, security architecture, and AI from the field — honest takes for practitioners, not press releases.

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