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Best Fun Restaurants in Headingley

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41 restaurants available nearby

A photo of The Keg Steakhouse + Bar - St. James restaurant
4.7
Exceptional(3130)
Price: Expensive
• Steakhouse • Birchwood/Silver Heights
Booked 64 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
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
4.6
Exceptional(4189)
Price: Expensive
• Steakhouse • Southwest Winnipeg
Booked 92 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 Rec Room - Winnipeg Seasons of Tuxedo restaurant
3.8
Excellent(354)
Price: Moderate
• Contemporary Canadian • Southwest Winnipeg
Booked 11 times today
The Rec Room redefines the meaning of fun with exciting arcade games, attractions, mouth-watering eats and live entertainment all packed under one roof. We’re Canada’s premier “eats & entertainment” hot spot!For reservations of parties of 13 guests or more, please call the venue directly. We kindly request our guests refrain from making multiple reservations for a single large party. While we will do our best to accommodate large groups, we cannot guarantee multiple reservations will be seated together.
A photo of The Keg Steakhouse + Bar - Garry Street restaurant
4.5
Awesome(3230)
Price: Expensive
• Steakhouse • South Portage
Booked 56 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 Cibo Waterfront Cafe restaurant
4.7
Exceptional(2087)
Price: Expensive
• Italian • Exchange District
Booked 30 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 Earls Kitchen + Bar - 300 Main Street restaurant
4.4
Awesome(731)
Price: Expensive
• American • Winnipeg
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 Next Door restaurant
4.7
Exceptional(32)
Price: Moderate
• Pub • Winnipeg
Booked 11 times today
Led by Good Neighbour Brewing Co, Next Door is a restaurant and neighbourhood gathering space – located right next to the brewery on Sherbrook Street – made for good beer, good eats, and good times!Our friends Stefan, Nyk, and Jesse (from Kosmo's Food Cantina and Hoagie Boyz) are powering the food menu with fun new takes on everyday food done really well and, of course, made to have you reaching for your pint of beer.Interested in hosting an event with us? Give us a shout at hello@nextdoorwpg.com and we can chat about what the event could look like including custom menus, signature cocktails, or maybe even a brewery tour.
A photo of James Avenue Pumphouse restaurant
4.6
Exceptional(771)
Price: Moderate
• International • Winnipeg
Booked 21 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 529 Wellington restaurant
4.8
Exceptional(1893)
Price: Very Expensive
• Steak • Little Italy/Corydon Village
Booked 17 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.

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Discover best fun restaurants in Headingley

Discover the vibrant and enjoyable dining scene in Winnipeg, Headingley, a delightful area that promises a fun-filled culinary experience. Whether you're looking for a lively spot to celebrate a special occasion or just a casual evening out, the restaurants in this region offer a perfect mix of ambiance and delectable cuisine that caters to the keyword 'fun'. Each establishment is designed to enhance your dining experience with unique themes, engaging environments, and exceptional service, ensuring every meal is memorable. The area is known for its eclectic food offerings ranging from gourmet meals to comforting local favorites, all served in settings that boast distinct character and charm. Diners can expect to find menus that are both innovative and satisfying, featuring dishes prepared by skilled chefs who prioritize quality and creativity. Experience the best of Winnipeg's hospitality with restaurants that not only promise a great meal but also a truly enjoyable atmosphere. This region's dining establishments are dedicated to providing an experience that is both entertaining and satisfying, making it a top choice for anyone looking for a fun dining destination.

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