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Best Comfort Food Restaurants in Headingley

Price

$$
$$$
$$$$

Cuisine

AmericanItalianFusion / EclecticBarbecueComfort FoodCanadian

Regions

Winnipeg

Neighborhoods

Birchwood/Silver HeightsExchange DistrictLittle Italy/Corydon VillageRichmond WestSouthwest WinnipegWinnipeg

Top Rated

CharmingGood for business mealsGood for groupsGood for special occasionsGreat for fine winesHot spot

Dining Options

All dining options

Delivery only

Takeout only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

10 restaurants available nearby

A photo of Silver Heights Restaurant & The Heights Lounge restaurant

1. Silver Heights Restaurant & The Heights Lounge

4.4

Awesome(32)

$$$$Price: Moderate

• Canadian • Richmond West

The Silver Heights Restaurant opened its doors at 2169 Portage Avenue in June, 1957. Former cabbie Anthony Siwicki Sr. had no idea it would still be going strong today! His operating philosophy was simple: “Provide your guests with quick and friendly service, and to serve fresh, delicious quality food at a reasonable price”…and to keep it that way. The restaurant is now in its third generation going forward.Silver Heights Restaurant was slowly transformed from a coffee shop into a lounge and dining room and bar. The adjoining hardware store on the East side became the dining room. In 1964 Tony bought out his three partners and his three sons Jim, Dave and Allan have grown the business.

A photo of Underdogs restaurant

2. Underdogs

4.4

Awesome(133)

$$$$Price: Moderate

• American • Birchwood/Silver Heights

Booked 3 times today

Underdogs is a new local restaurant with creative comfort FOOD and a tasty BOOZE selection. We’re your home to enjoy the game or RALLY with your friends!

A photo of Kevin's Bistro restaurant

3. Kevin's Bistro

4.6

Exceptional(436)

$$$$Price: Moderate

• Comfort Food • Exchange District

Booked 17 times today

Steak chimichurri, fresh mussels, garlic butter shrimp, Mac & Cheese and much much more! Located in Winnipeg's Exchange District, Kevin's Bistro is cosy and comfortable with great cocktails and live music on the weekends!

A photo of The Rec Room - Winnipeg Seasons of Tuxedo restaurant

4. The Rec Room - Winnipeg Seasons of Tuxedo

4.1

Excellent(366)

$$$$Price: Moderate

• Contemporary Canadian • Southwest Winnipeg

Booked 6 times today

The Rec Room redefines the meaning of fun with exciting arcade games, attractions, mouth-watering eats and live entertainment all packed under one roof. We’re Canada’s premier “eats & entertainment” hot spot!For reservations of parties of 13 guests or more, please call the venue directly. We kindly request our guests refrain from making multiple reservations for a single large party. While we will do our best to accommodate large groups, we cannot guarantee multiple reservations will be seated together.

A photo of James Avenue Pumphouse restaurant

5. James Avenue Pumphouse

4.6

Exceptional(821)

$$$$Price: Moderate

• International • Winnipeg

Booked 17 times today

Welcome to James Avenue PumphouseAwarded Best New Restaurant 2021 by Ciao! Magazine!Come visit us and experience a diverse menu offering from our very own Executive Chef, Mark Merano.Complimenting the historical setting and relaxed ambiance is a menu that draws both on Manitoba culinary traditions and globally inspired comfort food. Pair it with our smart cocktail list, and your night is complete!

A photo of Cafe Carlo restaurant

6. Cafe Carlo

4.8

Exceptional(2606)

$$$$Price: Expensive

• Italian • Little Italy/Corydon Village

Booked 11 times today

One of Winnipeg’s most loved and consistent neighbourhood restaurants, Cafe Carlo’s warm, unpretentious atmosphere has been a staple since 1989. Cafe Carlo’s food and drinks are a big hello to the full flavours of the world with a flirtatious wink to Italy. Created to be craved with delicious dishes like Fett Chile, sometimes classic, sometimes modern and always fresh. Cafe Carlo’s sharing plates, pastas, seafood and daily specials offer something to be savoured with a big glass of wine or a cocktail.Join us for a satisfying experience as you run in to friends or make new ones.

A photo of Peasant Cookery restaurant

7. Peasant Cookery

4.5

Awesome(1613)

$$$$Price: Expensive

• Contemporary European • Exchange District

Booked 8 times today

Peasant Cookery is located in the heart of Winnipeg's Exchange District. Made from scratch, European inspired dishes are prepared daily and served with care and attention to detail. Pair your dish with cocktails, local craft beers, or wine and enjoy in the dining room, lounge, or on the patio, and always with your favourite people.

A photo of Next Door restaurant

8. Next Door

4.5

Awesome(48)

$$$$Price: Moderate

• Pub • Winnipeg

Booked 38 times today

Led by Good Neighbour Brewing Co, Next Door is a restaurant and neighbourhood gathering space – located right next to the brewery on Sherbrook Street – made for good beer, good eats, and good times!Our friends Stefan, Nyk, and Jesse (from Kosmo's Food Cantina and Hoagie Boyz) are powering the food menu with fun new takes on everyday food done really well and, of course, made to have you reaching for your pint of beer.Interested in hosting an event with us? Give us a shout at hello@nextdoorwpg.com and we can chat about what the event could look like including custom menus, signature cocktails, or maybe even a brewery tour.

A photo of Montana's BBQ & Bar - Winnipeg - Sterling Lyon restaurant

9. Montana's BBQ & Bar - Winnipeg - Sterling Lyon

4.0

Excellent(0)

$$$$Price: Moderate

• Unspecified • Winnipeg

Montana's BBQ & BAR is a Canadian comfort food restaurant and sports bar that is famous for barbecue cuisine. Enjoy in-house smoked pork ribs, beef brisket, grilled steaks and juicy burgers which are paired perfectly with catching the game. Montana's Winnipeg celebrates fun-to-eat, finger-licking smoked and barbecued comfort food that breaks the 'proper' rules. Located near Eric Coy Arena & Assiniboine Park Zoo in the Southern end of Winnpeg. Experience the fun, casual and unpretentious vibe, where you can laugh heartily, cheer on the game and enjoy your friends and family. We can't wait to serve you.

A photo of Montana's BBQ & Bar - Winnipeg - Polo Park restaurant

10. Montana's BBQ & Bar - Winnipeg - Polo Park

4.0

Excellent(13)

$$$$Price: Moderate

• Unspecified • Winnipeg

Booked 1 time today

Montana's BBQ & BAR is a Canadian comfort food restaurant and sports bar that is famous for barbecue cuisine. Enjoy in-house smoked pork ribs, beef brisket, grilled steaks and juicy burgers which are paired perfectly with catching the game. Montana's Winnipeg celebrates fun-to-eat, finger-licking smoked and barbecued comfort food that breaks the 'proper' rules. Located near Scotiabank Theatre & Sargent Park in the heart of Polo Park. Experience the fun, casual and unpretentious vibe, where you can laugh heartily, cheer on the game and enjoy your friends and family. We can't wait to serve you.

See what locals rave about

From verified diners like you

From verified diners like you

N
Nicolle
Winnipeg / Manitoba •1 review
5.0
Dined 1 day ago
Good food in a comfortable setting. Owners and staff make you feel welcome. Not a large menu but what ever you choose for dinner will be great.
More info
Silver Heights Restaurant & The Heights LoungePrice: Moderate• Canadian• Richmond West
•
4.4
J
Jim
Winnipeg / Manitoba •3 reviews
5.0
Dined 4 days ago
We always enjoy our dinners at Kevins. Staff is friendly and happy. We both had 2 different Mac and Cheese, which were delicious . As an appetizer we had the lettuce wraps, the lettuce was crispy, just the way we like it.
More info
Kevin's BistroPrice: Moderate• Comfort Food• Exchange District
•
4.6
W
W Scott
San Antonio •3 reviews
5.0
Dined 6 days ago
The food and value and service were all exceptional. My only complaint is that there was a LOUD patron near us and due to tables being sort of close, we were forced to listen to his swearing and constant banter. We would go back though as everything else was excellent.
More info
Cafe CarloPrice: Expensive• Italian• Little Italy/Corydon Village
•
4.8
A
Andrea
Winnipeg / Manitoba •1 review
5.0
Dined 7 days ago
The wings and burger were so delicious . The menu is varied.
More info
UnderdogsPrice: Moderate• American• Birchwood/Silver Heights
•
4.4
S
Sheldon
Winnipeg / Manitoba •2 reviews
5.0
Dined on Jan 1, 2025
For a family get together for my son’s 14 birthday, it was a good experience. The food was good, came quickly and was good value. The only nuisance was getting to the washrooms from the restaurant, you either go down stairs and around or through an employee kiosk to get to them.
More info
The Rec Room - Winnipeg Seasons of TuxedoPrice: Moderate• Contemporary Canadian• Southwest Winnipeg
•
4.1

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