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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
4.6
Exceptional(1023)
Price: Expensive
• Global, International • Headingley
Booked 2 times 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(652)
Price: Expensive
• Italian • Winnipeg
Booked 10 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
4.6
Exceptional(3259)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 50 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 The Keg Steakhouse + Bar - Southside restaurant
4.7
Exceptional(4347)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 69 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
4.7
Exceptional(1325)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 5 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 - Garry Street restaurant
4.7
Exceptional(3340)
Price: Expensive
• Steakhouse • South Portage
Booked 28 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 Cibo Waterfront Cafe restaurant
4.7
Exceptional(2114)
Price: Expensive
• Italian • Exchange District
Booked 22 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
4.9
Exceptional(1928)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 8 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 Peasant Cookery restaurant
4.5
Awesome(1613)
Price: Expensive
• Contemporary European • Exchange District
Booked 8 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 Oval Room Brasserie – Fort Garry Hotel restaurant
4.6
Exceptional(471)
Price: Very Expensive
• French • Winnipeg
Booked 14 times today
Under the creative direction of Chef de Cuisine Kyle Lew, Oval Room Brasserie offers a wide selection of classic brasserie and bistro dishes for breakfast, lunch and dinner.With menu options ranging from sharing plates to dinners for two and everything in between, plus an extensive cocktail and wine selection curated by our Wine Director, Christopher Sprague, Oval Room Brasserie is the perfect spot to start your day or wrap up your day with family, friends or colleagues.Our philosophy is simple: we combine the BEST ingredients with the most traditional methods to produce OUTSTANDING quality food.

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See what locals rave about

From verified diners like you
From verified diners like you
  • Blair
    Vancouver / British Columbia •5 reviews
    5.0
    Dined 1 day ago
    The food was absolutely delicious and Michael made our experience amazing. Appreciate the perfect table for the perfect evening.
    More info
    The Gates on RoblinPrice: Expensive• Global, International• Headingley
    4.6
  • Nissa
    Winnipeg / Manitoba •1 review
    5.0
    Dined 2 days ago
    It was my first time going, I took my 2 kids (ages 2 and 6) and my partner. The service we received was outstanding, the food was incredible. I definitely recommend going. Absolutely wonder and lovely evening, especially thanks to our server for being as amazing as he was. Everyone who served us and helped in a big or small way made the evening just that much better. All your hard work shows ladies and gents keep it up.
    More info
    The Keg Steakhouse + Bar - St. JamesPrice: Expensive• Steakhouse• Birchwood/Silver Heights
    4.6
  • ToddVIP
    Winnipeg / Manitoba •23 reviews
    5.0
    Dined 2 days ago
    Everything was really good, right from the start. We were seated within 5 minutes of our reservation time. Our server, Courtney, took it from there. Within a couple minutes she greeted us and took our drink order. We had some fresh bread while waiting for our food. Both our steaks were cooked perfectly. I had a rib steak and it was nearly melt in your mouth tender and tasted incredible. She had sirloin and lobster. Coked exactly as requested and she ate more than she wanted to, because it tasted so good. We skipped dessert this time because we didn’t have room. I have to give a shout out to Courtney. She was a great server. Very personable and attentive. She was around just the right amount. Her energy was awesome and she was an absolute delight to have as our server. If she is your server, yo are a lucky patron.
    More info
    The Keg Steakhouse + Bar - SouthsidePrice: Expensive• Steakhouse• Southwest Winnipeg
    4.7
  • Emily
    Winnipeg / Manitoba •1 review
    5.0
    Dined 2 days ago
    Our table placement was absolutely perfect, tucked into a little corner in the back. We had an older gentleman as our waiter and it was the best service we have received in a while. The food and drinks were also amazing with fantastic recommendations. Second year in a row coming here for Valentine’s Day and will 100% do it for upcoming years.
    More info
    Alena Rustic ItalianPrice: Expensive• Italian• Winnipeg
    4.8
  • David
    Phoenix / Arizona •6 reviews
    5.0
    Dined on Jan 23, 2025
    Have dined here on a number of occasions. Room is beautiful. Staff attentive. Though a half hour early for our reservation the host went out of his way to accommodate us. Was greatly appreciated. Food is always good and was last evening as well.
    More info
    Gather Craft Kitchen & Bar at Assiniboine ParkPrice: Expensive• Contemporary Canadian• Winnipeg
    4.7

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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