Winnipeg Steakhouse Guide

Winnipeg Steakhouse Guide: Find the Best Steaks in the City

The thought of a perfectly cooked steak makes your taste buds tingle and your heart race. 

And if you happen to be in the heart of the Canadian prairies, there’s no better place to embark on a culinary adventure in search of the juiciest, most flavorful steaks than Winnipeg.

Winnipeg is a city that’s often underrated when it comes to its culinary scene, but when it comes to steak, we’ve got some hidden gems that are sure to delight your palate.

Join me as we venture through the sizzling hotspots, cozy hideaways, and upscale establishments that serve up the finest cuts of beef, prepared to perfection. 

529 Wellington 

529 Wellington

Address: 529 Wellington Crescent, Winnipeg, MB R3M 0B9, Canada 


Contact number: 204 487 8325 

Operating hours: Monday to Friday: 11 am – 2 pm; 4:30 pm – 10 pm; Saturday: 4:30 pm – 10 pm; Sunday: 4:30 pm – 9 pm  

Must-order menu items: Ribeye Steak, Tenderloin Steak, Veal Chop, Beef Wellington 

Price range: $$ average 

Founded in 2001, 529 Wellington has transformed from a historical mansion into a culinary haven. 

The steakhouse is located in a stunning 1912-built home that was once the residence of Sir William Stephenson, a key figure in British intelligence during World War II. 

This historical backdrop adds a touch of charm and elegance to the dining experience, making it a perfect blend of old-world opulence and modern dining.

Ribeye Steak at 529 Wellington in Winnipeg

When it comes to the menu, 529 Wellington doesn’t just offer great steaks; it boasts a selection that leaves a lasting impression. For those seeking the finest cuts, the Ribeye Steak is a prime choice. 

Served with a perfect sear, it’s a succulent, well-marbled piece of meat that encapsulates the essence of a top-tier steak.

The Tenderloin Steak is another standout option, appealing to those who prefer a leaner, buttery texture. 

For a unique twist, the Veal Chop is a must-try. Its delicate flavor and tender meat are a delightful diversion from the classic beef selections, showcasing the restaurant’s culinary diversity.

Perhaps the pinnacle of their menu is the Beef Wellington. A dish steeped in history, this masterpiece brings together a perfectly seared filet mignon, a layer of duxelles, and a flaky pastry. 

The Keg Steakhouse + Bar – Garry Street 

The Keg Steakhouse + Bar - Garry Street

Address: 115 Garry St, Winnipeg, MB R3C 1G5, Canada 


Contact number: 204 942 7619 

Operating hours: Monday to Thursday: 4 pm – 11 pm; Friday to Saturday: 4 pm  – midnight; Sunday: 4 pm – 10 pm 

Must-order menu items: Prime Rib, Filet Mignon, Teriyaki Sirloin, Top Sirloin, Baseball Top Sirloin, Sirloin Oscar, New York Striploin, Peppercorn New York, Rib Steak 

Price range: $$ average

The history of The Keg Steakhouse + Bar can be traced back to the early 1970s when it was originally established in Vancouver, British Columbia. Over the years, it has grown into a celebrated chain of restaurants across Canada and the United States. 

The Winnipeg location on Garry Street proudly continues the tradition of excellence in the heart of the city.

Its menu boasts a tantalizing array of options, but a few stand out as must-order items.

Prime Rib at The Keg Steakhouse + Bar - Garry Street in Winnipeg

The Prime Rib at The Keg is a culinary masterpiece. Served with all the classic trimmings, it’s a melt-in-your-mouth experience that’s sure to leave your taste buds singing with delight.

Next up is the Filet Mignon, a tender cut of beef that’s celebrated for its unmatched tenderness. If you prefer it perfectly grilled or with a sumptuous sauce, the Filet Mignon is a top choice for those seeking a refined dining experience.

If you’re in the mood for something a bit different, try the Teriyaki Sirloin. This dish showcases a delightful fusion of flavors, with a teriyaki glaze that adds a sweet and savory twist to the juicy sirloin.

The Top Sirloin is a classic choice, offering a robust beefy flavor. And if you’re feeling particularly hearty, consider the Baseball Top Sirloin, a substantial and juicy cut that’s sure to satisfy even the heartiest appetites.

For a more opulent dining experience, indulge in the Sirloin Oscar. This dish combines a succulent sirloin steak with lump crab, asparagus, and Béarnaise sauce, resulting in a combination of flavors that will leave you craving more.

The New York Striploin and Peppercorn New York are perfect choices for those who appreciate the bold flavors of a striploin cut. 

The New York Striploin boasts a classic preparation, while the Peppercorn New York adds a zesty kick with its peppercorn crust and creamy peppercorn sauce.

Last but certainly not least, the Rib Steak offers a satisfyingly rich and flavorful option. The marbling in this cut makes it a standout choice for those who appreciate the depth of flavor that well-prepared beef can deliver.

Chop Steakhouse & Bar 

Chop Steakhouse & Bar

Address: 1750 Sargent Ave, Winnipeg, MB R3H 0C7, Canada


Contact number: 204 788 2015 

Operating hours: Monday to Friday: 11:30 am – midnight; Saturday: 3 pm – midnight; Sunday: 3 pm – 11 pm 

Must-order menu items: Chop Signature Filet, Dry-Aged Ribeye, Bone-In Prime Rib, New York Striploin, Canadian Heritage Angus Beef

Price range: $$ average

When you step into Chop, you’re in for a treat. While the entire menu is a feast for the senses, a few dishes stand out as must-orders. 

The Chop Signature Filet is a culinary masterpiece, featuring a melt-in-your-mouth, center-cut tenderloin steak. 

It’s paired with your choice of delicious sauces and sides, making it an experience you won’t soon forget.

Dry-Aged Ribeye at The Chop Steakhouse & Bar in Winnipeg

For those who appreciate the rich, intense flavors of dry-aged beef, the Dry-Aged Ribeye is a top recommendation. Aged to enhance its taste and tenderness, this ribeye is a true delicacy. 

The bone-in prime rib is another showstopper, boasting an impressive presentation and an equally impressive taste. The slow-roasting technique ensures that each bite is succulent and full of flavor.

If you’re a fan of New York Striploin, Chop Steakhouse & Bar serves up a New York Striploin that’s juicy, flavorful, and perfectly seasoned. 

It’s a classic for a reason, and Chop’s rendition doesn’t disappoint.

For the discerning steak enthusiast, the Canadian Heritage Angus Beef is known for its exceptional marbling and depth of flavor and is sourced from the finest ranches in Canada. 

Each bite is an homage to the country’s rich culinary heritage.

Rae & Jerry’s Steak House

Rae & Jerry’s Steak House

Address: 1405 Portage Ave, Winnipeg, MB R3G 0W1, Canada 


Contact number: 204 783 6155

Operating hours: Monday to Saturday: 4 pm – 10 pm; Sunday: 4 pm – 8:30 pm 

Must-order menu items: Steak au Poivre, Bone-in Ribeye, New York Strip, Filet Mignon, Prime Rib

Price range: $$ average

Rae & Jerry’s story began more than 50 years ago, with the vision of its founders, Rae Levy and Jerry Shore. Their passion for creating a memorable dining experience led to the establishment of this iconic steakhouse. 

Over the years, Rae & Jerry’s has remained dedicated to the art of crafting the perfect steak. It’s a place where tradition meets excellence, offering a warm and inviting ambiance that has stood the test of time.

Steak au Poivre at Rae & Jerry’s Steakhouse in Winnipeg

When it comes to must-order menu items at Rae & Jerry’s, it’s hard to go wrong with its offerings. One standout choice is the Steak au Poivre, a dish that beautifully showcases the art of steak preparation. 

This culinary masterpiece features a tender filet mignon delicately coated in a cracked peppercorn crust and accompanied by a creamy brandy sauce. 

The combination of flavors and textures in this dish is a true delight, making it a classic and one of the restaurant’s most sought-after selections.

For those who appreciate a hearty, flavorful steak, order the Bone-in Ribeye. This well-marbled steak is prepared over a wood-fired grill, bringing out the rich, smoky flavors that carnivores crave. 

If you’re in the mood for something equally delicious but more budget-friendly, the New York Strip is a wise pick. 

This lean and flavorful steak is skillfully cooked over the wood-fired grill, ensuring a mouthwatering experience without breaking the bank. 

It’s a testament to Rae & Jerry’s commitment to offering exceptional quality without compromising on affordability.

Hy’s Steakhouse and Cocktail Bar 

Hy’s Steakhouse and Cocktail Bar

Address: Richardson Building, 1 Lombard Ave Main Floor, Winnipeg, MB R3B 0X3, Canada


Contact number: 204 942 1000

Operating hours: Monday to Thursday: 11:30 am – 10 pm; Friday: 11:30 am – 11 pm; Saturday: 3 pm – 11 pm; Sunday: 3 pm – 9 pm  

Must-order menu items: Filet Mignon, New York Striploin, Prime Rib, Porterhouse, T-Bone

Price range: $$ average

With a history dating back to its opening in 1958, this establishment has long been celebrated for its commitment to delivering the finest dining experience, centered around top-quality steaks and seafood.

Over the decades, it has remained true to these core values, consistently providing guests with an atmosphere of timeless elegance and impeccable hospitality. Its enduring appeal is a testament to its dedication to quality and tradition.

When dining at Hy’s Steakhouse and Cocktail Bar, you’ll be delighted to discover a diverse selection of steaks, each prepared with the utmost care and expertise.

The Filet Mignon is a classic favorite. This cut of meat is renowned for its lean and tender qualities, making it a perfect choice for those who relish a refined, melt-in-your-mouth steak experience. 

For those who prefer a steak with a bit more character, the New York Striploin is known for its rich, beefy flavor and juicy texture. It’s the perfect selection if you’re seeking a more substantial meal.

Indulgence knows no bounds when you opt for the Prime Rib. This sumptuous cut of meat is celebrated for its richness and decadence. 

Porterhouse at Hy’s Steakhouse and Cocktail Bar in Winnipeg

If you’re sharing a meal with a friend or loved one, consider the Porterhouse. 

This large, bone-in cut of meat is designed for those who enjoy both a New York Striploin and a Filet Mignon on one plate, making it an ideal choice for a delightful shared dining experience.

Lastly, the T-Bone is another appealing option. Similar to the Porterhouse, it features both a New York Striploin and a smaller Filet Mignon side. It’s an excellent choice for those who appreciate variety in their steaks.

Bailey’s Restaurant & Bar 

Bailey’s Restaurant & Bar

Address: 185 Lombard Ave, Winnipeg, MB R3B 0W4, Canada


Contact number: 204 944 1180 

Operating hours: Monday to Thursday: 11 am – 9 pm; Friday: 11 am – 10 pm; Saturday: 4 pm – 10 pm; Sunday: 4 pm – 9 pm 

Must-order menu items: Prime New York Strip, Prime Dry-Aged Ribeye, Prime Bone-In Ribeye, Prime Filet Mignon, Prime Petite Filet Mignon, Prime Porterhouse, Prime Tomahawk Ribeye

Price range: $$ average

When you step into Bailey’s, be prepared to embark on a carnivorous journey like no other. The must-order menu items here are a testament to the restaurant’s dedication to top-notch beef. 

Prime New York Strip at Bailey’s Restaurant & Bar in Winnipeg

Its Prime New York Strip is a succulent and generously portioned cut that boasts exquisite marbling and flavor. 

If you’re feeling particularly indulgent, opt for the Prime Dry-Aged Ribeye. This menu item is a showstopper. 

The dry-aging process adds a depth of flavor and tenderness that elevates this steak to a level of perfection that’s hard to match. 

The Prime Bone-In Ribeye, another delicious option, offers an extra layer of taste due to the bone, making it a true carnivore’s delight.

For those who prefer a leaner cut, the Prime Filet Mignon at Bailey’s is tender, buttery, and oozing with flavor. 

When it comes to celebrating a special occasion or sharing an unforgettable meal, the Prime Porterhouse is a popular choice. It combines the rich flavor of the New York Strip with the tender Filet Mignon, all in one grand steak. 

Montana’s BBQ & Bar 

Montana’s BBQ & Bar

Address: 630 Sterling Lyon Pkwy, Winnipeg, MB R3P 1E9, Canada


Contact number: 204 500 1210

Operating hours: Sunday to Thursday” 11”30 am – 10 pm; Friday and Saturday: 11:30 am – 11 pm 

Must-order menu items: AAA Sirloin, AAA New York Striploin, AAA Cowboy Rib Steak, AAA Filet Mignon

Price range: $$ average

Montana’s, originally established as a small, rustic eatery, has evolved into a beloved steakhouse over the years. The relaxing and homey atmosphere, reminiscent of a cozy log cabin, sets the perfect stage for an evening of delectable dining.

Montana’s prides itself on serving only the finest quality steaks, all sourced from premium AAA beef. The AAA Sirloin, known for its robust flavor and tender texture, is a popular choice among patrons. 

AAA Cowboy Rib Steak at Montana’s BBQ & Bar in Winnipeg

For those special occasions, or when you’re in the mood for an exceptionally tender cut, the AAA Filet Mignon is a splendid option.

Each steak is masterfully prepared and cooked to perfection, ensuring that you experience the ultimate steakhouse delight. 

Montana’s also offers a variety of delectable sides and sauces to complement your meal, such as loaded baked potatoes, sautéed mushrooms, and peppercorn sauce.

Simon’s Steaks 

Address: 1 Forks Market Rd #132, Winnipeg, MB R3C 4Y3, Canada


Contact number: 204 691 8939

Operating hours: Sunday to Thursday: 11 am – 9 pm; Friday and Saturday: 11 am – 10 pm 

Must-order menu items: Dry Aged Ribeye, New York Strip, Filet Mignon, Porterhouse 

Price range: $$ average

Founded by Simon himself, a passionate steak lover, the steakhouse has stood the test of time, evolving with the changing tastes of its discerning patrons.

When you step into Simon’s Steaks, you’ll find yourself in a cozy and welcoming atmosphere that radiates warmth and elegance. 

The aroma of sizzling steaks on the grill tantalizes your senses, setting the stage for a gastronomic journey you won’t soon forget.

The Dry Aged Ribeye is a true carnivore’s delight. This cut is known for its intense marbling, which imparts a remarkable depth of flavor. 

The aging process transforms this already exquisite cut into a tender and savory masterpiece that will leave you craving more.

The New York Strip is another top pick, showcasing a perfect balance of tenderness and juiciness. This classic cut has a mouthwatering sear on the outside and a succulent, medium-rare interior.

Filet Mignon at Simon’s Steaks in Winnipeg

For those seeking the epitome of tenderness, the Filet Mignon is known for its velvety texture and mild, buttery flavor. 

A prime filet at Simon’s is like cutting into a cloud of exquisite beef, and it’s often paired with delectable sauces and accompaniments.

Last but certainly not least, the Porterhouse is a carnivore’s dream come true. This menu item embodies the best of both worlds, featuring both a strip steak and a filet mignon on a single bone. 

It’s a true indulgence, perfect for sharing with a fellow steak enthusiast or as a solo endeavor if you’re feeling particularly ravenous.

Silver Heights Restaurant & Lounge 

Silver Heights Restaurant & Lounge

Address: 2169 Portage Ave, Winnipeg, MB R3J 0L7, Canada


Contact number: 204 889 7246

Operating hours: Monday to Thursday: 11 am – 12 am; Friday and Saturday: 11 am 2 am 

Must-order menu items: New York Strip, Filet Mignon, Prime Rib, Ribeye Steak, Cowboy Steak

Price range: $$ average

When you step into the welcoming ambiance of Silver Heights, you’re met with a cozy and rustic atmosphere that perfectly complements the hearty menu. 

Let’s talk about the stars of the show — the must-order menu items that have left countless diners in awe.

First on the list is the New York Strip, a classic favorite for steak connoisseurs. The beautifully marbled, tender beef offers a juicy, flavorful experience that is truly unforgettable. 

If you’re in the mood for something a bit more refined, the Filet Mignon is an excellent choice. This melt-in-your-mouth cut is celebrated for its tenderness and is often prepared with a subtle seasoning that allows the natural flavors to shine.

For those who crave a hearty, indulgent meal, the Prime Rib should be your go-to. Slow-roasted, it’s tender, juicy, and packed with flavor, making it an ideal choice for a special occasion or when you’re simply in the mood for a sumptuous treat. 

Ribeye Steak at Silver Heights Restaurant & Lounge in Winnipeg

Silver Heights also offers a savory Ribeye Steak, known for its rich marbling and robust, beefy taste that leaves your taste buds dancing.

Last but certainly not least is the Cowboy Steak, a choice that’s not for the faint of heart. This thick, bone-in ribeye is perfect for those who appreciate a substantial, flavorful steak. 

The Cowboy Steak at Silver Heights is expertly seasoned and cooked to your preferred doneness, making it a delightful challenge for even the heartiest of appetites.

Tony Roma’s 

Tony Roma’s

Address: 656 St James St, Winnipeg, MB R3G 3Z5, Canada


Contact number: 204 949 9426

Operating hours: Monday to Thursday: 3 pm – 10 pm; Friday and Saturday: 3 pm – 11 pm 

Must-order menu items: New York Strip, Top Sirloin, Ribeye, Filet Medallions, Peppercorn New York

Price range: $$ average

Tony Roma’s Steakhouse in Winnipeg owes its beginnings to the vision of its founder, Tony Roma, who embarked on a culinary journey in the late 1960s. 

With a passion for bringing the finest cuts of meat to the table, he opened his first restaurant in North Miami Beach, Florida. 

As the years passed, Tony Roma’s became renowned for its delectable steaks, signature barbecue sauces, and a warm, welcoming atmosphere. 

Fast forward to today, and the Winnipeg location, situated on a bustling street, is a testament to Tony’s legacy of excellence.

When it comes to the menu at Tony Roma’s Steakhouse, one can expect an array of mouthwatering options. 

Peppercorn New York at Tony Roma’s in Winnipeg

However, the standout stars that are simply a must-order include the New York Strip, Top Sirloin, Ribeye, Filet Medallions, and Peppercorn New York. 

The New York Strip, featuring rich marbling that bursts with flavor, is a prime choice for those who appreciate a hearty, well-seasoned steak. 

The Top Sirloin boasts a wonderful tenderness that never disappoints. The Ribeye, a favorite among steak aficionados, is generously marbled and delivers a full-bodied, succulent taste. 

The Filet Medallions are an absolute delight, offering a melt-in-your-mouth experience, while the Peppercorn New York adds a zesty twist to your steak with a delightful peppercorn sauce. 

Pair your selection with an extensive list of side dishes and, of course, one of its signature cocktails, and you’ve got a dining experience that’s truly second to none.