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Best Date Night Restaurants in Headingley

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34 restaurants available nearby

A photo of Hy's Steakhouse - Winnipeg restaurant
4.7
Exceptional(2227)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 16 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(2617)
Price: Expensive
• Italian • Little Italy/Corydon Village
Booked 19 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 Kevin's Bistro restaurant
4.6
Exceptional(442)
Price: Moderate
• Comfort Food • Exchange District
Booked 23 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 Cibo Waterfront Cafe restaurant
4.7
Exceptional(2120)
Price: Expensive
• Italian • Exchange District
Booked 33 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 The Keg Steakhouse + Bar - Garry Street restaurant
4.7
Exceptional(3370)
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 James Avenue Pumphouse restaurant
4.7
Exceptional(831)
Price: Moderate
• International • Winnipeg
Booked 45 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 Select Start - Arcade Restolounge restaurant
3.9
Excellent(7)
Price: Expensive
• Asian • Winnipeg
Booked 27 times today
Step into a neon dream at Select Start Arcade Restolounge, where vibrant neon lights, retro arcade games, and delicious food await. Located in Winnipeg, this restaurant offers an immersive experience reminiscent of a high-rise in downtown Tokyo. Dive into nostalgia with classic arcade games like Pac-Man, Galaga, and Street Fighter. Challenge friends to pinball or explore the latest virtual reality games, all while enjoying an energetic atmosphere filled with electronic music. Select Start also features a mouthwatering menu of Asian-inspired dishes, including flavorful ramen, juicy dumplings, crispy spring rolls, and fresh sushi. Pair your meal with a refreshing cocktail or craft beer from their extensive selection. Whether you're seeking a fun night out with friends, a unique date night, or a place to relax with great food and entertainment, Select Start is your perfect destination. Step out of the ordinary and into a neon dream – Select Start is waiting for you!
A photo of Pizzeria Gusto restaurant
4.7
Exceptional(1860)
Price: Expensive
• Pizzeria • Academy Road
Booked 27 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 Peasant Cookery restaurant
4.5
Awesome(1620)
Price: Expensive
• Contemporary European • Exchange District
Booked 18 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 JOEY Kenaston restaurant
4.7
Exceptional(130)
Price: Expensive
• American • Southwest Winnipeg
Booked 23 times today
JOEY Restaurants marries iconic hospitality with a handcrafted, locally and globally-inspired menu from award-winning chefs, to bring an unparalleled guest experience. Instead of just one chef, JOEY has a whole team of celebrated Executive Chefs bringing you an experience you can't get anywhere else. JOEY Kenaston's inviting space features sleek modern materials and a patio for upscale yet casual dining, sipping or socializing.

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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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