The Top Restaurants in Charleswood

A Quest for Chow: The Top Restaurants in Charleswood, Winnipeg

As a foodie always on the hunt for our next grub in Winnipeg, I’ve tried pretty much every restaurant in most neighborhoods. If you find yourself in Charleswood, you won’t be disappointed with the selection of amazing food there!

From what I noticed over the years of dining out in this snazzy neighborhood, there are lots of pizza parlors, and they all deserve a spot on our list.

It’s not just pizza, though, there are multitudes of other options too, from tasty Mexican fare and delectable Japanese cuisine to exquisite Italian delicacies and classic bar food–you’ll be spoilt for choice.

I want to save you the trouble of having mediocre food in this ‘hood. So far, here are some of the best restaurants in Charleswood!

1. Taverna Rodos Restaurant & Lounge

Location5114 Roblin Boulevard, Winnipeg, MB R3R 0G9, Canada
Contact Number+1 204-615-2232
Opening HoursMonday to Thursday: 9 AM to 8:30 PM

Friday to Saturday: 9 AM to 9 PM

Sunday: 9 AM to 8 PM

Must-Try ItemsShrimp souvlaki


Reuben sandwich


Price$$$ - Expensive

Authentic Greek food can be a hit or miss for me, but thank goodness it’s all hit after I chanced upon Taverna Rodos. They’re open for all meals of the day, but I usually stop by this place at dinnertime when they have the ribs and souvlaki combo.

I’ve had my fair share of pita, probably too much for just one lifetime, but the gyro at Taverna Rodos is just too good. They do a mix of roasted beef and lamb and slather it in rich tzatziki sauce–my mouth is watering just writing about it!

While this restaurant does serve insanely good Greek fare, I like the fact that they also cater to other palates. There are other food options such as steaks, pasta, burgers, and more!

If you’re here for the non-Greek selection, I highly recommend the Reuben sandwich!

Another thing I like about this place is the big portions. You’ll know I’m not kidding once you try it!

2. Gondola Pizza 

Location4910 Roblin Boulevard, Winnipeg, MB R3R 0G7, Canada
Contact Number+1 204-837-9999
Opening HoursSunday to Tuesday: 4 PM to 10 PM

Wednesday to Thursday: 4 PM to 11 PM

Friday to Saturday: 4 PM to 12 AM

Must-Try ItemsViva La Mexicana

Chicken fajita

Perogy pizza

Price$$ - Average

If you’re a sucker for thin-crust pizza, Gondola is a spot you don’t want to miss. In my book, they’re one of the best thin-crust pizza places in the city!

They’re very consistent, too–they have multiple locations in Winnipeg but the quality remains the same for all branches. No wonder so many people I know keep coming back to Gondola.

While I love a classic pepperoni or Hawaiian pizza, I actually like Gondola for its specialty and premium pizzas.

Viva La Mexicana is one of my go-to’s here; it has a fresh salsa base with green and banana peppers, crushed taco chips, and a cheese blend. I’m a dip person so I always ask for additional sour cream and salsa dips for this!

Another pizza you should try here is the Sweet Chili Thai. I never thought a sweet chili sauce would work on pizza, but it does!

3. TacoTime Roblin

Location5198 Roblin Boulevard, Winnipeg, MB R3R 0G6, Canada
Contact Number+1 204-885-5115
Opening HoursMonday to Sunday: 11 AM to 10 PM
Must-Try ItemsRanch chicken burrito

Mexi-fries deluxe

Price$$ - Average

I love a good burrito or taco when I’m in a hurry or on the go, and I’ve found TacoTime on Roblin to be a good spot for a fix.

I like a contrasting taste whenever I’m having food that’s rich in spices, so I always get the ranch chicken burrito and still request an extra dip! I typically get this along with a black bean and corn quesadilla and a Mexi-fries deluxe.

While this is a great place for a taco fix, I highly suggest coming here at non-peak hours ’cause it can get pretty packed. Just a little tip so you can steer clear of long queues!

4. Signature Pizza And Salads Ltd.

Location5120 Roblin Boulevard, Winnipeg, MB R3R 0G9, Canada
Contact Number+1-204-837-1234
Opening HoursSunday to Wednesday: 4 PM to 10 PM

Thursday to Saturday: 4 PM to 11 PM

Must-Try ItemsGourmet veggie

Chicken Florentine

Price$$$ - Expensive

This pizza place is a challenge to find, but I’m glad I finally did! It’s tucked in the back of the building where Taverna Rodos is.

The crust is amazing and has a good chew to it, and they definitely don’t skimp on the toppings. Plus, their pizza is not covered in grease, and that’s always a good thing.

I’d say their sauce has a sweeter base, so that’s something to consider if you’re coming here. 

I prefer a spicier base but their sauce works just as well! Signature also serves their pizza on a gluten-free crust for a minimal extra fee.

I’ll admit, the price points here are higher than those of a typical pizza chain in the city, but for a place that’s locally owned and serving fresh, quality ingredients, I think it’s well worth the extra dollars.

Last I heard, they get their deli meat from ​​Winnipeg Old Country; locals supporting locals is always a two thumbs up in my book!

5. Iyara Thai Restaurant

Location5606 Roblin Boulevard #8, Winnipeg, MB R3R 0H2, Canada
Contact Number+1 204-219-1269
Opening HoursMonday: Closed

Tuesday to Sunday: 3 PM to 9 PM

Must-Try ItemsMassaman curry

Tom yum soup

Price$$ - Average

The world just got a little better when Iyara Thai opened its doors to Winnipegians. Everything about this place is wonderful, and I can’t recommend it enough!

The Massaman curry here is possibly one of the best I’ve tasted in the city. The portion of rice noodles and plain rice was just right, and it had the perfect amount of heat. 

Their red curry is to die for, too! I’d recommend getting a side of rice as there tends to be more curry than rice when you get this combo. You’d need all that rice for the amazing spice blend!

I personally am a tom yum person, and the broth here is just as tangy and delicious as when I tried a bunch of local eateries in Thailand.

6. Sorrento’s Bar & Pizzeria

Location3900 Grant Avenue, Winnipeg, MB R3R 3C5, Canada
Contact Number+1 204-837-5063
Opening HoursMonday to Saturday: 11 AM to 10 PM

Sunday: 12 PM to 9 PM

Must-Try ItemsFour cheese alfredo

Italian meatball panini

Price$$$ - Expensive

Whenever I get a hankering for Italian food, Sorrento’s is one of my go-to’s. The four cheese alfredo is my favorite pasta to devour here! The chicken mushroom tortellini in tomato cream sauce is a banger option, too.

The restaurant also has lots of pizza options, but coincidentally, I have a soft spot for the namesake Sorrento pizza. It’s a medley of pepperoni, salami, ham, and green peppers with lots of mozzarella and mushrooms.

They have an extensive menu, so I’d recommend this place if you’re craving for more than just pizza! I’d say that their price range is a bit on the higher side, but I think it’s worth it, especially since the servings are huge.

For dessert, I cannot recommend the strawberry cheesecake enough. It’s oozing with champagne mousse, strawberry swirls, and dark chocolate bits!

7. Pappas Greek Food & Steak

— Media credit: kathleeneloise

Location3318 Roblin Boulevard, Winnipeg, MB R3R 0C5, Canada
Contact Number+1 204-889-5504
Opening HoursSunday to Monday: Closed

Tuesday to Friday: 12 PM to 9 PM

Saturday: 4 PM to 9 PM

Must-Try ItemsMoussaka

Lamb chops

Avgolemono soup

Price$$$ - Expensive

There’s not a lot of Greek spots in the city, but another one that I’m happy to recommend is Pappas on Roblin. Their food is on the pricier side, but I can see the appeal in their use of fresh and high-quality ingredients.

I love the traditional horiatiki salad bathing in feta cheese–I never fail to order this whenever I’m here. For the main course, I often switch between the Greek-style lamb chops and the classic moussaka casserole.

If you’re a first-timer at this joint, get the Pappas platter for a taste of their bestsellers: avgolemono (lemon rice) soup, chicken souvlaki, Greek ribs, tzatziki, and a whole lot more. It’s so worth the price tag.

One of the best things about this place is they have a selection of homemade sauces that perfectly complement their menu.