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Best Casual Restaurants in Headingley

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54 restaurants available nearby

A photo of Alena Rustic Italian restaurant
1. Alena Rustic Italian
4.8
Exceptional(610)
Price: Expensive
• Italian • Winnipeg
Booked 18 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
2. The Keg Steakhouse + Bar - St. James
4.7
Exceptional(3138)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 27 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
Booked 2 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 2 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 Original Joe's - Winnipeg - Unicity restaurant
5. Original Joe's - Winnipeg - Unicity
5.0
Exceptional(2)
Price: Moderate
• Canadian • Winnipeg
Original Joe's is a place that welcomes everyone. We have craveable classics, down-to-earth vibes and a friendly team looking to brighten your day! Original Joe's Unicity is located just inside the perimeter highway on Portage Avenue West. We've been catering to Winnipeg's St. James neighbourhood for nearly a decade. Our patio is one of the largest in this part of the city (you'll have to come check it out) and boasts a beautiful exterior TV to watch summer sporting events on. We're a short drive away from the Assiniboia Downs where you can enjoy live horse racing or the Bell MTS Iceplex, which is open year-round. You can take in a few rounds of golf at the Glen Dale Golf & Country Club or visit the Red River Exhibition Park for various events. Wherever you decide to spend your time in Unicity, you can never go wrong by ending (or starting) your day with OJ's. Our patio welcomes dogs along with good vibes!
A photo of Boston Pizza - Charleswood restaurant
6. Boston Pizza - Charleswood
4.3
Awesome(3)
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 Boston Pizza - Birchwood restaurant
7. Boston Pizza - Birchwood
4.4
Awesome(3)
Price: Moderate
• Pizzeria • Birchwood/Silver Heights
Booked 1 time today
Boston Pizza is a family restaurant and sports bar with great food, like pizza, pasta, wings, and more!
A photo of Cafe Carlo restaurant
8. Cafe Carlo
4.7
Exceptional(2575)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 22 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
9. Gather Craft Kitchen & Bar at Assiniboine Park
4.6
Exceptional(1237)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 37 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 Pizzeria Gusto restaurant
10. Pizzeria Gusto
4.6
Exceptional(1822)
Price: Expensive
• Pizzeria • Academy Road
Booked 34 times today
Pizzeria Gusto is an extension of my dinner table, where friends, family and loved ones gather together to share conversation, laughter, food and wine. The aromas and sounds are a constant reminder of centuries old Italian traditions, which instantly welcome you to the family.We believe that pizza is the perfect food. A blank canvas that has unlimited possibilities in both taste and texture. By using fresh local produce and authentic Italian ingredients your experience will surely have you saying "Bellissimo"!Our wood burning oven comes from Reggelo, 20 km from Florence. The Valoriani oven is hand crafted by a family of artisans that has been perfecting their skills for 5 generations. Its domed brick roof and 650 degree temperature is the perfect vessel for creating the perfect pizza.

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