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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
1. The Gates on Roblin
4.5
Awesome(1024)
Price: Expensive
• Global, International • Headingley
Booked 5 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
2. Alena Rustic Italian
4.8
Exceptional(667)
Price: Expensive
• Italian • Winnipeg
Booked 17 times today
Coming Soon!
A photo of The Keg Steakhouse + Bar - St. James restaurant
3. The Keg Steakhouse + Bar - St. James
4.6
Exceptional(3280)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 77 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. The Keg Steakhouse + Bar - Southside
4.7
Exceptional(4385)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 59 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
5. Gather Craft Kitchen & Bar at Assiniboine Park
4.7
Exceptional(1336)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 31 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
6. The Keg Steakhouse + Bar - Garry Street
4.6
Exceptional(3370)
Price: Expensive
• Steakhouse • South Portage
Booked 57 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
7. Cibo Waterfront Cafe
4.7
Exceptional(2120)
Price: Expensive
• Italian • Exchange District
Booked 28 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
8. 529 Wellington
4.9
Exceptional(1937)
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 Oval Room Brasserie – Fort Garry Hotel restaurant
9. Oval Room Brasserie – Fort Garry Hotel
4.7
Exceptional(483)
Price: Very Expensive
• French • Winnipeg
Booked 23 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.
A photo of Peasant Cookery restaurant
10. Peasant Cookery
4.5
Awesome(1620)
Price: Expensive
• Contemporary European • Exchange District
Booked 16 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.

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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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