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Best Neighbourhood Gem Restaurants in Headingley

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18 restaurants available nearby

A photo of The Gates on Roblin restaurant
4.7
Exceptional(1015)
Price: Expensive
• Global, International • Headingley
Booked 3 times today
The Gates on Roblin is a gem in the Headingley neighborhood. It's a beautifully restored country estate with excellent service and a wide range of delicious food. Customers love the ambiance and the top-notch service. The food is always fresh and prepared to perfection. It's a perfect spot for special occasions, with reviews consistently praising its excellent food, service, and ambiance.
A photo of The Keg Steakhouse + Bar - St. James restaurant
4.7
Exceptional(3136)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 23 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 Alena Rustic Italian restaurant
4.8
Exceptional(610)
Price: Expensive
• Italian • Winnipeg
Booked 13 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - Southside restaurant
4.6
Exceptional(4192)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 57 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 Pizzeria Gusto restaurant
4.6
Exceptional(1821)
Price: Expensive
• Pizzeria • Academy Road
Booked 25 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 The Keg Steakhouse + Bar - Garry Street restaurant
4.6
Exceptional(3236)
Price: Expensive
• Steakhouse • South Portage
Booked 48 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 Cafe Carlo restaurant
4.7
Exceptional(2575)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 20 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 529 Wellington restaurant
4.8
Exceptional(1894)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 23 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 Merchant Kitchen restaurant
4.6
Exceptional(1349)
Price: Expensive
• Global, International • Exchange District
Booked 11 times today
EXCITING. FLAVOURFUL. SHARED.The Merchant Kitchen is an idea conceptualized by travel and adventure. Honouring the traditional ingredients, flavours, and techniques of Asia and Latin America, while incorporating the freshest local ingredients possible is our mantra.Exploring cities and towns along the equator, tasting their food carts, and visiting the local markets have allowed us to bring that to the table an experience that enables guests to escape routine and enjoy flavours with friends and family.
A photo of Hy's Steakhouse - Winnipeg restaurant
4.7
Exceptional(2199)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 40 times today
Hy’s Winnipeg is a local favorite since 1958, located at the famous corner of Portage and Main. Hy’s offers 2 levels of dining for lunch and dinner in an upscale, classic yet contemporary atmosphere. In the warmer months, a spectacular new patio is perfect for al fresco dining. Whether you join us in the lively cocktail lounge or a quiet corner of the restaurant, Hy’s signature Canada Prime beef and hand crafted cocktails combined with professional and unpretentious service is sure to make your experience memorable. Join us for Happy Hour from 3 PM -6 PM Valet parking - Hy's guests can valet park at the Fairmont for a special rate of $16+ tax daily after 3pm. Self Park at the Richardson Parkade and bring your ticket for validation. Payment methods include: Visa/Mastercard/Discover/Cash/ApplePay/Debit/Hy's & Gotham Gift Cards *** We are unable to accept Pre-Paid Credit Cards***

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See what locals rave about

From verified diners like you
From verified diners like you
  • Linda
    Winnipeg / Manitoba •5 reviews
    5.0
    Dined 2 days ago
    We had a lovely evening, sharing the porterhouse special that included prawns and scallops. It was a busy night there but we were served immediately and courses were timed perfectly. Our only regret was that we had no room for the tiramisu!
    More info
    Alena Rustic ItalianPrice: Expensive• Italian• Winnipeg
    4.8
  • Tammy
    Winnipeg / Manitoba •3 reviews
    5.0
    Dined 3 days ago
    Well we had a bad experience before this one and the manager reached out to us to apologize and make things right. We finally decided to go last night and use the offer to make things right. We’ve visited this establishment for at least over 10 years, and last night reminded us that this is why we come to the KEG. Everything was delightful, delicious and our server Scott was super AMAZING. Thank you to the manager and thank you Scott for the amazing and delightful hospitality and service.
    More info
    The Keg Steakhouse + Bar - SouthsidePrice: Expensive• Steakhouse• Southwest Winnipeg
    4.6
  • Linseyvip
    Winnipeg / Manitoba •11 reviews
    5.0
    Dined 3 days ago
    Justin was so great! Super attentive and remembered us from the last time he served us. Tracy was super great also! Food was so good. Super efficient, super tasty, great value! Can't wait to go back !
    More info
    The Keg Steakhouse + Bar - St. JamesPrice: Expensive• Steakhouse• Birchwood/Silver Heights
    4.7
  • Chris
    Winnipeg / Manitoba •1 review
    5.0
    Dined 4 days ago
    We chose the early sitting of 5:30 knowing most people would still be commuting home from work before heading out for dinner. It was a good plan because we had the opportunity to experience a calm and intimate meal. Walking to the building from the car was so lovely because the Christmas lights were on and snow was gently falling. Gorgeous. The staff were so kind and attentive but not intrusive. And the food! Wow! My wife had the half rack of lamb and it was so tender she didn’t even need the knife. I had the prime rib and it was probably the best in the city. It was a lovely and relaxing evening and a perfect way to start the weekend off.
    More info
    The Gates on RoblinPrice: Expensive• Global, International• Headingley
    4.7
  • Shane
    Winnipeg / Manitoba •2 reviews
    5.0
    Dined 5 days ago
    Food was very good and our server Matti was AMAZING!! Very attentive and high product knowledge.
    More info
    Pizzeria GustoPrice: Expensive• Pizzeria• Academy Road
    4.6

Discover best neighborhood gem restaurants in Headingley

Discover the charm of neighborhood gems in Winnipeg, Manitoba, specifically in the quaint area of Headingley. This page features a curated selection of restaurants that embody the spirit and appeal of this unique locale. Each restaurant offers a welcoming atmosphere that perfectly blends local culture with exceptional culinary experiences, making them standout dining destinations in the region. Whether you're seeking a cozy spot for a romantic dinner or a lively setting for a family gathering, these establishments ensure a memorable meal with their commitment to quality and service. The dining scene in Headingley is characterized by its intimate yet vibrant ambiance, attracting both locals and visitors who appreciate fine food in a relaxed environment. Explore these top-rated venues and experience the best of local dining where every meal is served with a touch of neighborhood charm.

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