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Best Casual Restaurants in Headingley

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27 restaurants available nearby

A photo of Alena Rustic Italian restaurant
1. Alena Rustic Italian
4.8
Exceptional(623)
Price: Expensive
• Italian • Winnipeg
Booked 24 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
2. The Keg Steakhouse + Bar - St. James
4.6
Exceptional(3178)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 74 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
4.4
Awesome(21)
Price: Moderate
• Canadian • Richmond West
Booked 4 times today
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
Booked 4 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 Boston Pizza - Charleswood restaurant
5. Boston Pizza - Charleswood
4.2
Awesome(4)
Price: Moderate
• Pizzeria • Charleswood
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
4.6
Exceptional(4249)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 107 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(2585)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 24 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
8. Peasant Cookery
4.5
Awesome(1601)
Price: Expensive
• Contemporary European • Exchange District
Booked 24 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 Moxies - Kenaston restaurant
9. Moxies - Kenaston
4.7
Exceptional(259)
Price: Moderate
• Contemporary American • Southwest Winnipeg
Booked 15 times today
Moxies restaurant is a contemporary casual restaurant offering a globally inspired menu and hand crafted cocktails in a vibrant and interactive atmosphere. Moxies has over 50 locations across Canada and 6 US locations in Dallas, Houston and Miami. We are excited for you to experience everything Moxies has to offer! Our Culinary Architect, Chef Brandon Thordarson, brings fiery passion and creativity to the Moxies experience. Deftly melding ethnic inspired cuisine with classic comfort foods and savvy fusion fare, we showcase a broad spectrum of the world’s finest flavors. From coast to coast, we focus on quality food made with fresh ingredients served in a stylish, comfortable & casual environment.Enjoy a late-night snack in our lounge or come in for a memorable meal in our beautiful dining room. Moxie’s Kenaston is located in southwest Winnipeg, at Kenaston (Route 90) and Columbia Drive and within easy stroll to tourism hotspot shopping area Kenaston Common.
A photo of The Keg Steakhouse + Bar - Garry Street restaurant
10. The Keg Steakhouse + Bar - Garry Street
4.6
Exceptional(3269)
Price: Expensive
• Steakhouse • South Portage
Booked 73 times today
The Keg Steakhouse & 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 & 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.

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