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Best Restaurants for Outdoor Dining in Headingley

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8 restaurants available nearby

A photo of Pizzeria Gusto restaurant
1. Pizzeria Gusto
4.6
Exceptional(1821)
Price: Expensive
• Pizzeria • Academy Road
Booked 31 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.
A photo of 529 Wellington restaurant
2. 529 Wellington
4.8
Exceptional(1894)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 14 times today
Experience the splendor of 529 Wellington, Winnipeg’s Premier Steakhouse. The beautifully restored historic mansion offers intimate dining in 8 elegantly appointed rooms, as well as a beautiful 2-tiered riverside terrace for alfresco dining. 529 serves exclusively Prime Beef, the best available in Canada, as well as fresh fish and seafood. The restaurant is proud to offer Manitoba’s highest rated wine list, Wine Spectator Magazine’s Best of Award of Excellence since 2004. Please note: 529 Wellington is a two-storied building without an elevator. Please indicate if there are any mobility issues for any diners in the party.*Please note 529 Wellington does not permit outside food and drink due to our food safety program.
A photo of The Keg Steakhouse + Bar - Garry Street restaurant
3. The Keg Steakhouse + Bar - Garry Street
4.6
Exceptional(3236)
Price: Expensive
• Steakhouse • South Portage
Booked 51 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.
A photo of Earls Kitchen + Bar - Polo Park - Winnipeg restaurant
4. Earls Kitchen + Bar - Polo Park - Winnipeg
4.6
Exceptional(649)
Price: Expensive
• American • Polo Park
Booked 17 times today
Welcome to Earls Polo Park, your destination for an unforgettable dining experience in Winnipeg. Step into our outdoor oasis, featuring a vibrant bar and a lush patio that seamlessly blends covered and open-air seating. Located near the popular Polo Park Shopping Centre, we provide a central and convenient location for you to unwind. Delight your taste buds with our enticing daily features, carefully crafted to showcase the best flavours of the season. Join us during Happy Hour and late-night Happy Hour to enjoy refreshing drinks and delectable bites that are sure to satisfy. Join us and experience the best of Winnipeg's culinary scene, with daily features, Happy Hour, and late-night indulgences that will leave you wanting more. Your table is ready. We can't wait to see you!
A photo of Nicolino's Restaurant restaurant
5. Nicolino's Restaurant
4.8
Exceptional(1043)
Price: Moderate
• Italian • Pembina Strip
Booked 17 times today
Nicolino's Cucina Italiana continues to serve Winnipeg's finest Italian cuisine using the highest quality ingredients and traditional recipes. Everything here is made from scratch and made to order, you'll taste the difference that homemade food offers in every bite! Whether you sit in our beautiful dining room, lounge or spacious patio, each offers you the dining experience of your choice. Be it a date night, a family dinner, a business meeting, or a get together with friends we know it will be over great food, wine, signature cocktails, and service. We are excited to serve you and have you here as our special guest.Our customers and our customer service are our top priorities. We know life gets busy so please call us if you need to cancel or reschedule your reservation. We do allow a 15 minute grace period for your reservation. In wanting to look after all of our guests we allow 1.5 hours for our tables of 2 and 2 hours for our larger groups. Buon Appetito!
A photo of Pasquale’s Ristorante Italiano restaurant
6. Pasquale’s Ristorante Italiano
4.7
Exceptional(894)
Price: Moderate
• Italian • St. Boniface
Booked 8 times today
Proudly serving Winnipeg Classic Italian cuisine since 1977 . How do we stay in business that long? Easy its our product. lasagna , Cheese Cannelloni, Eggplant Parmesan, Veal and Chicken Parmesan Our Marinara and Bolognese sauce to our breads and dressings. All made in house from scratch by our chefs. Special diets we got you covered we serve Gluten free, Vegan and Vegetarian items. table for 2 or 40 Pasquale's private Dining is great for the whole la famiglia. And Our 50 seat roof top Patio is a must in our hot Winnipeg summers Can't get to us call for our city wide catering and delivery service and New Online Ordering system and App. Quick and convenient. Please advise for handicapped or elderly customers request main floor dining.
A photo of Corrientes Argentine Pizzeria restaurant
7. Corrientes Argentine Pizzeria
4.6
Exceptional(853)
Price: Moderate
• Argentinean • Exchange District
Booked 7 times today
A pizza culture like no other in the world thrives on Corrientes Avenue, Buenos Aires. Now on Bannatyne Avenue, Winnipeg
A photo of La Roca restaurant
8. La Roca
4.4
Awesome(878)
Price: Moderate
• Mexican • South Portage
Booked 3 times today
Located in the heart of Winnipeg's downtown, La Roca is your gateway to a genuine Mexican culinary experience and hand-crafted margaritas, sangria, rare tequilas, and a vast selection of beer and wine. With a two-level patio offering live music every Thursday, Friday, and Saturday, our restaurant caters to a diverse range of patrons, from young adults to seniors. Our vibrant atmosphere sets the stage for an excellent dining adventure. Enjoy a dynamic ambiance, exceptional Mexican cuisine, and the warmth of our hospitality at La Roca—a destination that captures the essence of Mexico in the heart of Winnipeg.

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