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Best Date Night Restaurants in Headingley

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27 restaurants available nearby

A photo of Hy's Steakhouse - Winnipeg restaurant
4.8
Exceptional(2230)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 8 times today
Hy’s Steakhouse & Cocktail Bar is a local favourite and Canada's Premium Steakhouse since 1955, located at the famous corner of Portage and Main. Join us in the lively cocktail lounge or a quiet corner of the restaurant for Hy’s contemporary steakhouse menu featuring our signature Canada Prime beef and hand crafted cocktails. Professional, unpretentious service is sure to make your experience memorable. In the warmer months, a spectacular new patio is perfect for al fresco dining. Hy's has one of the city's best Happy Hours daily from 3 PM -6 PM with live music in the lounge. 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***
A photo of Cafe Carlo restaurant
4.8
Exceptional(2606)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 11 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 James Avenue Pumphouse restaurant
4.6
Exceptional(821)
Price: Moderate
• International • Winnipeg
Booked 17 times today
James Avenue Pumphouse is the perfect spot for a date night. With its beautiful historical setting and vibrant ambiance, it's described as 'cool and fun' by many reviewers. The menu is diverse, drawing on both local Manitoba traditions and global comfort food, while the drinks are praised for being 'solid'. The service is consistently lauded for being 'great', adding to the overall excellent experience. So, if you're looking for a charming, lively spot for a romantic night out, this place is a must-visit!
A photo of Gather Craft Kitchen & Bar at Assiniboine Park restaurant
4.7
Exceptional(1325)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 4 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 Pizzeria Gusto restaurant
4.7
Exceptional(1851)
Price: Expensive
• Pizzeria • Academy Road
Booked 8 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 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 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 529 Wellington restaurant
4.9
Exceptional(1928)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 9 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 Vida Cucina Italia at The Fort Garry Hotel restaurant
4.7
Exceptional(202)
Price: Very Expensive
• Italian • Winnipeg
Booked 4 times today
Traditional Italian cuisine with a modern twist - Vida Cucina Italia by Italy's culinary master, Chef Rosanna Marziale and Resident Chef Fabrizio Rossi combines passion, attention to detail and the finest ingredients from Italy together with a flawless execution. Located in the historical Fort Garry Hotel - adding a touch of both modern dining and old-world charm.

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See what locals rave about

From verified diners like you
From verified diners like you
  • JerryVIP
    Winnipeg / Manitoba •28 reviews
    5.0
    Dined 1 day ago
    Excellent food & service. The perfect level of spice in the TNT Shrimp appetizer and the DanDan main. Well done!
    More info
    James Avenue PumphousePrice: Moderate• International• Winnipeg
    4.6
  • KrisVIP
    Winnipeg / Manitoba •7 reviews
    5.0
    Dined 3 days ago
    This is the Best Steak House in Winnipeg! Having been to dozens of Steak Houses for decades, I love that Hy’s offers many Steak current and traditional options with accompaniments. I appreciate that the Servers and Staff are professional and exceptional. The ambience and atmosphere are excellent. I think this is the perfect Dining experience to please and reward yourself and impress your companion(s). It is definitely a favourite Restaurant for any and all special occasions! I highly recommend it! You’ll love it, guaranteed!
    More info
    Hy's Steakhouse - WinnipegPrice: Very Expensive• Steakhouse• Exchange District
    4.8
  • Marcel
    Winnipeg / Manitoba •3 reviews
    5.0
    Dined 3 days ago
    First time at Hermano’s yesterday. I had been wanting to go there for some time now. Did not disappoint. Food was spectacular. Balsamic drizzle on the ribeye was a game changer. Server never offered us a second round of drinks. It Valentine’s Day. Seemed to want to rush us out a little. You pay for what you get. So it’s not cheap. $200 for the 2 of us including a drink each and an appetizer each. It’s a must try in my book. Would definitely go back.
    More info
    Hermanos SteakhousePrice: Moderate• South American• Exchange District
    4.2
  • Laura
    Winnipeg / Manitoba •1 review
    5.0
    Dined 3 days ago
    We made a reservation and asked for a specific table and were very pleased that Cibo accommodated our request. The ambiance is beautiful and we wanted a table to look out at the river. We were going to the theatre and were a bit pressed for time, our server was fantastic to ensure that our orders were expedited quickly and our food was served promptly, hot, and delicious!
    More info
    Cibo Waterfront CafePrice: Expensive• Italian• Exchange District
    4.7
  • 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 date night restaurants in Headingley

Discover the perfect ambiance for your next date night in Winnipeg, Manitoba, specifically in the charming areas of Winnipeg and Headingley. These locations boast a variety of restaurants that cater specifically to making your evening special and memorable. Whether you're looking for a cozy, intimate setting or a more vibrant, lively atmosphere, you'll find options that perfectly match your date night expectations. Each establishment offers a unique blend of exceptional service, exquisite culinary creations, and a welcoming environment, ensuring every moment is cherished. The dining scene in Winnipeg and Headingley is diverse and well-suited for romantic outings, featuring establishments that range from upscale gourmet to quaint bistros, all emphasizing quality and a great dining experience. These restaurants are known for their attention to detail, from thoughtfully curated menus to ambient lighting and decor, all designed to enhance your dining experience. Ideal for couples seeking a delightful evening out, these venues prioritize creating an atmosphere where memories are made, making them top picks for anyone planning a date night in this scenic locale.

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