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Best Romantic Restaurants in Headingley

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25 restaurants available nearby

A photo of The Gates on Roblin restaurant
4.7
Exceptional(1015)
Price: Expensive
• Global, International • Headingley
Booked 1 time today
The Gates on Roblin is described as a 'beautiful setting' perfect for 'special occasions'. Reviewers highlight the 'quiet and intimate' ambiance, 'excellent service', and 'delicious food'. It's the ideal place to 'celebrate an anniversary', 'have a wonderful time' and enjoy a 'lovely dinner out'. The 'beautifully presented' food, 'friendly service', and 'great value' all contribute to a romantic dining experience.
A photo of Alena Rustic Italian restaurant
4.8
Exceptional(610)
Price: Expensive
• Italian • Winnipeg
Booked 10 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
4.7
Exceptional(3136)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 32 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 Gather Craft Kitchen & Bar at Assiniboine Park restaurant
4.6
Exceptional(1236)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 32 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 The Keg Steakhouse + Bar - Southside restaurant
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 Cibo Waterfront Cafe restaurant
4.6
Exceptional(2088)
Price: Expensive
• Italian • Exchange District
Booked 24 times today
Take your tastebuds on a trip to the Mediterranean at Cibo Waterfront!Inspired by our historic waterfront location, Cibo pairs a quality all-day menu with craft cocktails and upscale wines. Menu highlights from our scratch kitchen include hand stretched pizzas, several unique takes on bruschetta, and an eclectic compilation of modern and classic Mediterranean cuisine. Our chic, brick building lights up in the day time sunshine or provides a warm atmosphere in the evening, with unique and stunning views of Winnipeg’s iconic Red River and Esplanade Riel. A comfortable ambiance to celebrate life.
A photo of 529 Wellington restaurant
4.8
Exceptional(1894)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 17 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
4.6
Exceptional(3234)
Price: Expensive
• Steakhouse • South Portage
Booked 49 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 Peasant Cookery restaurant
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.
A photo of Cafe Carlo restaurant
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.

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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 1 day 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 2 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
    4.7
  • Linseyvip
    Winnipeg / Manitoba •11 reviews
    5.0
    Dined 2 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 3 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
  • Colleen
    Winnipeg / Manitoba •5 reviews
    5.0
    Dined 5 days ago
    Nicky was a fabulous waitress. Helped to make it an extra special meal.
    More info
    Gather Craft Kitchen & Bar at Assiniboine ParkPrice: Expensive• Contemporary Canadian• Winnipeg
    4.6

Discover best romantic restaurants in Headingley

Discover the enchanting world of romantic dining in Winnipeg and Headingley, where culinary experiences are tailored to create unforgettable evenings. Nestled in the scenic landscapes of Manitoba, these locations boast an array of restaurants that specialize in providing a cozy, intimate setting ideal for those special moments with a loved one. From the soft glow of candlelight to the exquisite culinary offerings, each establishment is dedicated to crafting an atmosphere that enhances the romance of your meal. Patrons can expect top-notch service, beautifully presented dishes, and a selection of fine wines that perfectly complement the flavors of your dinner. The dining scene in this area is renowned for its commitment to quality and attention to detail, ensuring every dining experience is both delightful and memorable. Whether you’re celebrating an anniversary or planning a quiet evening out, Winnipeg and Headingley offer the perfect backdrop for romance. Indulge in the charm and elegance of these dining spots and make your next dinner date truly spectacular.

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