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Best Date Night Restaurants in Headingley

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31 restaurants available nearby

A photo of The Keg Steakhouse + Bar - St. James restaurant
4.6
Exceptional(3177)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
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 Hy's Steakhouse - Winnipeg restaurant
4.7
Exceptional(2207)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 24 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***
A photo of Cafe Carlo restaurant
4.7
Exceptional(2586)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 24 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
4.7
Exceptional(788)
Price: Moderate
• International • Winnipeg
Booked 47 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 Kevin's Bistro restaurant
4.6
Exceptional(417)
Price: Moderate
• Comfort Food • Exchange District
Booked 12 times today
Steak chimichurri, fresh mussels, garlic butter shrimp, Mac & Cheese and much much more! Located in Winnipeg's Exchange District, Kevin's Bistro is cosy and comfortable with great cocktails and live music on the weekends!
A photo of Gather Craft Kitchen & Bar at Assiniboine Park restaurant
4.6
Exceptional(1270)
Price: Expensive
• Contemporary Canadian • Winnipeg
Booked 62 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 Peasant Cookery restaurant
4.5
Awesome(1601)
Price: Expensive
• Contemporary European • Exchange District
Booked 26 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 Nicolino's Restaurant restaurant
4.7
Exceptional(1052)
Price: Moderate
• Italian • Pembina Strip
Booked 9 times today
Nicolino's Cucina Italiana continues to serve Winnipeg's finest Italian cuisine using the highest quality ingredients and traditional recipes. Everything here is made from scratch and made to order, you'll taste the difference that homemade food offers in every bite! Whether you sit in our beautiful dining room, lounge or spacious patio, each offers you the dining experience of your choice. Be it a date night, a family dinner, a business meeting, or a get together with friends we know it will be over great food, wine, signature cocktails, and service. We are excited to serve you and have you here as our special guest.Our customers and our customer service are our top priorities. We know life gets busy so please call us if you need to cancel or reschedule your reservation. We do allow a 15 minute grace period for your reservation. In wanting to look after all of our guests we allow 1.5 hours for our tables of 2 and 2 hours for our larger groups. Buon Appetito!
A photo of Vida Cucina Italia at The Fort Garry Hotel restaurant
4.7
Exceptional(191)
Price: Very Expensive
• Italian • Winnipeg
Booked 6 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.
A photo of Cibo Waterfront Cafe restaurant
4.7
Exceptional(2101)
Price: Expensive
• Italian • Exchange District
Booked 25 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.

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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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