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Best Restaurants with a Happy Hour in Headingley

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18 restaurants available nearby

A photo of The Keg Steakhouse + Bar - St. James restaurant
1. The Keg Steakhouse + Bar - St. James
4.7
Exceptional(3137)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 37 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 Underdogs restaurant
2. Underdogs
4.4
Awesome(132)
Price: Moderate
• American • Birchwood/Silver Heights
Booked 3 times today
Underdogs is a new local restaurant with creative comfort FOOD and a tasty BOOZE selection. We’re your home to enjoy the game or RALLY with your friends!
A photo of The Keg Steakhouse + Bar - Southside restaurant
3. The Keg Steakhouse + Bar - Southside
4.6
Exceptional(4192)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 55 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 - Garry Street restaurant
4. The Keg Steakhouse + Bar - Garry Street
4.6
Exceptional(3236)
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
5. James Avenue Pumphouse
4.6
Exceptional(774)
Price: Moderate
• International • Winnipeg
Booked 25 times today
Welcome to James Avenue PumphouseAwarded Best New Restaurant 2021 by Ciao! Magazine!Come visit us and experience a diverse menu offering from our very own Executive Chef, Mark Merano.Complimenting the historical setting and relaxed ambiance is a menu that draws both on Manitoba culinary traditions and globally inspired comfort food. Pair it with our smart cocktail list, and your night is complete!
A photo of Earls Kitchen + Bar - 300 Main Street restaurant
6. Earls Kitchen + Bar - 300 Main Street
4.4
Awesome(734)
Price: Expensive
• American • Winnipeg
Booked 74 times today
Welcome to Earls 300 Main, the vibrant heartbeat of downtown Winnipeg. Located near Canada Life Centre and Shaw Park, our restaurant is the perfect gathering place for sports enthusiasts seeking delicious food before or after the game. Host your corporate lunches and dinners with ease and enjoy the abundance of fresh plants and greenery as it creates a refreshing and inviting atmosphere for all to enjoy. As an added convenience, we also provide free heated underground parking accessible via Fort Street. Indulge in our daily features, unwind during Happy Hour, and keep the night going with late-night Happy Hour. Join us and experience the vibrant culinary and cultural scene of downtown Winnipeg. Your table is ready. We can't wait to see you!Receive free parking validation weeknights from 4:00 PM to close, weekends + holidays all day. Please note if you arrive before 4:00 PM you will not qualify for free parking validation.
A photo of Cibo Waterfront Cafe restaurant
7. Cibo Waterfront Cafe
4.7
Exceptional(2088)
Price: Expensive
• Italian • Exchange District
Booked 27 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 Hy's Steakhouse - Winnipeg restaurant
8. Hy's Steakhouse - Winnipeg
4.7
Exceptional(2199)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 29 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 CHOP Steakhouse & Bar - Winnipeg restaurant
9. CHOP Steakhouse & Bar - Winnipeg
4.6
Exceptional(2046)
Price: Expensive
• Steakhouse • St. James
Booked 19 times today
Chop was created for people who love sharing, connecting and everything steak. We are proud to offer a menu that shares our commitment to sustainable beef sourcing, serving high-quality cuts of 100% Canadian beef. It isn’t just the meat that’s special – it’s also how we cook it. Our Montague broiler cooks at up to 1800 °F, giving a beautiful crust and flavour to every steak! We slow roast our prime rib in a humidity-controlled oven, keeping it mouth-watering and tender. And we put this level of care into each of our hand-crafted drinks, and from-scratch dishes, including plant-based and seafood options, with something for everyone to enjoy. All of this quality comes with friendly hospitality in warm and energetic rooms. Open for lunch, happy hour, dinner and late-night!
A photo of The Merchant Kitchen restaurant
10. The Merchant Kitchen
4.6
Exceptional(1349)
Price: Expensive
• Global, International • Exchange District
Booked 11 times today
EXCITING. FLAVOURFUL. SHARED.The Merchant Kitchen is an idea conceptualized by travel and adventure. Honouring the traditional ingredients, flavours, and techniques of Asia and Latin America, while incorporating the freshest local ingredients possible is our mantra.Exploring cities and towns along the equator, tasting their food carts, and visiting the local markets have allowed us to bring that to the table an experience that enables guests to escape routine and enjoy flavours with friends and family.

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