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Best Casual Restaurants in Headingley

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29 restaurants available nearby

A photo of Alena Rustic Italian restaurant
1. Alena Rustic Italian
4.8
Exceptional(610)
Price: Expensive
• Italian • Winnipeg
Booked 10 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
2. The Keg Steakhouse + Bar - St. James
4.7
Exceptional(3136)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 31 times today
The Keg Steakhouse and Bar serves the finest cuts of succulent steak, aged for tenderness and grilled to perfection. Prime rib is a Keg specialty, slow roasted, hand carved and perfectly seasoned with special Keg spices. The restaurant also serves delicious seafood, memorable appetizers, crisp salads and decadent desserts. A casual ambiance and friendly, very knowledgeable staff are proud and reliable trademarks of The Keg Steakhouse and Bar. You will find a truly comfortable and satisfying dining atmosphere accompanied by a fun and up-scale bar setting where guests can enjoy an excellent wine list, signature Keg martinis, and fresh squeezed juice cocktails.
A photo of Silver Heights Restaurant & The Heights Lounge restaurant
3. Silver Heights Restaurant & The Heights Lounge
new
4.6
Exceptional(17)
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
4. Underdogs
4.4
Awesome(132)
Price: Moderate
• American • Birchwood/Silver Heights
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 Boston Pizza - Charleswood restaurant
5. Boston Pizza - Charleswood
4.3
Awesome(3)
Price: Moderate
• Pizzeria • Charleswood
Booked 1 time today
Boston Pizza is Canada’s No. 1 casual dining brand, serving more than 100 unique and delicious menu items such as gourmet pizzas and pastas, juicy burgers and our famous BP wings. We are located by the Varsity View sportsplex, Bell MTS Iceplex, Charleswood Curling Club, Assiniboine Park and Zoo, Eric Coy Arena, Canadian Mennonite University and the Outlet collection Winnipeg.
A photo of The Keg Steakhouse + Bar - Southside restaurant
6. The Keg Steakhouse + Bar - Southside
4.7
Exceptional(4192)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 61 times today
The Keg Steakhouse and Bar serves the finest cuts of succulent steak, aged for tenderness and grilled to perfection. Prime rib is a Keg specialty, slow roasted, hand carved and perfectly seasoned with special Keg spices. The restaurant also serves delicious seafood, memorable appetizers, crisp salads and decadent desserts. A casual ambiance and friendly, very knowledgeable staff are proud and reliable trademarks of The Keg Steakhouse and Bar. You will find a truly comfortable and satisfying dining atmosphere accompanied by a fun and up-scale bar setting where guests can enjoy an excellent wine list, signature Keg martinis, and fresh squeezed juice cocktails.
A photo of Cafe Carlo restaurant
7. Cafe Carlo
4.7
Exceptional(2575)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 18 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 Gather Craft Kitchen & Bar at Assiniboine Park restaurant
8. Gather Craft Kitchen & Bar at Assiniboine Park
4.6
Exceptional(1236)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 33 times today
Welcome to Gather Craft Kitchen & Bar –Globally Inspired Modern Prairie CuisineAround the world, people gather with food for celebration, ceremony, and connection. Gather Craft Kitchen & Bar, located in The Leaf at Assiniboine Park, explores food from across cultures, incorporating fresh, locally-sourced, and seasonal ingredients from our gardens. Craveable dishes incorporate traditional flavours and techniques from around the world, inspired by the nature that surrounds us all. Pickled, preserved, fermented or straight off the vine, local ingredients are creatively prepared to highlight the amazing growers and farmers in Manitoba. Inventive, botanical cocktails made with herbs grown in-house, seasonal fruits, and house-made syrups will delight the senses.
A photo of James Avenue Pumphouse restaurant
9. James Avenue Pumphouse
4.6
Exceptional(772)
Price: Moderate
• International • Winnipeg
Booked 36 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 Peasant Cookery restaurant
10. Peasant Cookery
4.5
Awesome(1594)
Price: Expensive
• Contemporary European • Exchange District
Booked 15 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.

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