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Best Restaurants with a Happy Hour in Headingley

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20 restaurants available nearby

A photo of The Keg Steakhouse + Bar - St. James restaurant
1. The Keg Steakhouse + Bar - St. James
4.6
Exceptional(3280)
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 Original Joe's - Winnipeg - Unicity restaurant
2. Original Joe's - Winnipeg - Unicity
4.6
Exceptional(6)
Price: Moderate
• Canadian • Winnipeg
Original Joe's is a place that welcomes everyone. We have craveable classics for lunch or dinner, down-to-earth vibes and a friendly team looking to brighten your day! Original Joe's Unicity is located just inside the perimeter highway on Portage Avenue West. We've been catering to Winnipeg's St. James neighbourhood for nearly a decade. Our patio is one of the largest in this part of the city (you'll have to come check it out) and boasts a beautiful exterior TV to watch summer sporting events on. We're a short drive away from the Assiniboia Downs where you can enjoy live horse racing or the Bell MTS Iceplex, which is open year-round. You can take in a few rounds of golf at the Glen Dale Golf & Country Club or visit the Red River Exhibition Park for various events. Wherever you decide to spend your time in Unicity, you can never go wrong by ending (or starting) your day with OJ's. Our patio welcomes dogs along with good vibes!
A photo of Underdogs restaurant
3. Underdogs
4.4
Awesome(132)
Price: Moderate
• American • Birchwood/Silver Heights
Booked 2 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
4. The Keg Steakhouse + Bar - Southside
4.7
Exceptional(4384)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 63 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
5. The Keg Steakhouse + Bar - Garry Street
4.7
Exceptional(3370)
Price: Expensive
• Steakhouse • South Portage
Booked 47 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 Earls Kitchen + Bar - 300 Main Street restaurant
6. Earls Kitchen + Bar - 300 Main Street
4.6
Exceptional(829)
Price: Expensive
• American • Winnipeg
Booked 57 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 Hy's Steakhouse - Winnipeg restaurant
7. Hy's Steakhouse - Winnipeg
4.7
Exceptional(2227)
Price: Very Expensive
• Steakhouse • Exchange District
Booked 17 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 CHOP Steakhouse & Bar - Winnipeg restaurant
8. CHOP Steakhouse & Bar - Winnipeg
4.6
Exceptional(2091)
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 James Avenue Pumphouse restaurant
9. James Avenue Pumphouse
4.7
Exceptional(831)
Price: Moderate
• International • Winnipeg
Booked 43 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 JOEY Kenaston restaurant
10. JOEY Kenaston
4.7
Exceptional(130)
Price: Expensive
• American • Southwest Winnipeg
Booked 31 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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