Vintage Dining Winnipeg's Oldest Restaurants

Vintage Dining: Winnipeg’s Oldest Restaurants

Growing up surrounded by the rich culinary tapestry of Winnipeg, I’ve witnessed the evolution of the city’s dining scene. 

From timeless classics that have withstood the test of time to hidden gems waiting to be discovered, Winnipeg boasts a diverse array of eateries that cater to every palate. 

In this exploration of the city’s gastronomic heritage, we’ll traverse through the alleys of nostalgia and savor the flavors that define our hometown’s comfort. 

So, join me on a journey through the city’s oldest and most cherished restaurants. 

1. Bailey’s Restaurant

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

Google Maps: Bailey's Restaurant

Contact DetailsPhone: +1 204-944-1180

Email: [email protected]

Operating HoursMonday 11 AM–9 PM

Tuesday 11 AM–9 PM

Wednesday 11 AM–9 PM

Thursday 11 AM–9 PM

Friday 11 AM–10 PM

Saturday 4–10 PM

Sunday 4–9 PM

Must-order ItemsChicken Satay, Baked French Onion Soup, Greek Salad, Sirloin Steak, Filet Mignon, Veal Madeira, Chicken Teriyaki Brochette, Pasta Chorizo Aribiatta, ClubHouse Wrap, Bailey's Famous Reuben Sandwich, Bailey's Guinness Cheeseburger
Price$$$ (Expensive)

Established in 1971, Bailey’s Restaurant has been serving delectable Italian and Canadian cuisine for over five decades. Bailey’s has become a local institution with a cozy ambiance and a menu that combines tradition and innovation. 

The restaurant features private dining rooms, providing an intimate setting for special occasions.

Its commitment to culinary excellence ensures that every dish is cooked to perfection, leaving patrons with a memorable dining experience. The staff at Bailey’s goes above and beyond to provide exceptional service. 

Their attentiveness, fun demeanor, and friendly charisma contribute to the restaurant’s welcoming atmosphere. Whether it’s a romantic date or a special celebration, Bailey’s upscale and classy setting makes it the perfect venue. 

For over 50 years, Bailey’s Restaurant has satisfied appetites with delicious cuisine and created lasting memories for Winnipeg’s discerning diners.

Pro Tip: 

Bailey’s is a popular spot, especially during peak hours. Consider making a reservation to secure your table and avoid waiting.

2. Rae & Jerry’s Steak House

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

Google Maps: Rae & Jerry's Steak House

Contact DetailsPhone: +1 204-783-6155

Email: [email protected]

Operating HoursMonday 4–10 PM

Tuesday 4–10 PM

Wednesday 4–10 PM

Thursday 4–10 PM

Friday 4–10 PM

Saturday 4–10 PM

Sunday 4–8:30 PM

Must-order ItemsShrimp Cocktail, Charcoal Broiled Rib Steak, Roast Prime Rib of Beef, Deluxe Cheeseburger, Grilled Filet of Fresh Salmon, Broiled Lobster Tail, Bar-B-Q Pork Spareribs, Fried Jumbo Shrimp, Veal Cutlet, Grilled Breast of Chicken
Price$$$ (Expensive)

Rae & Jerry’s has been a Winnipeg landmark since 1957. Known for its classic steakhouse fare, it’s a favorite for those seeking a taste of nostalgia and perfectly cooked steaks. 

The ambiance in Rae & Jerry’s feels like Old Hollywood, exuding a charming retro vibe that adds to the overall dining experience. The hostesses are polite and welcoming, setting the tone for a delightful evening.

The atmosphere is a unique blend of quiet sophistication and festive charm, making it easy to engage in conversations at your table. 

When it comes to the main attraction, the steak, it’s unparalleled. It’s always cooked to perfection, and the chefs at Rae & Jerry’s consistently deliver an exceptional dining experience. 

Moreover, the restaurant is attentive to dietary needs, with clear indications on the menu and a willingness to accommodate restrictions, ensuring that every patron enjoys a tailored and satisfying meal. 

Rae & Jerry’s continues to uphold its reputation as a timeless establishment that marries culinary excellence with unparalleled hospitality.

Pro Tip: 

Parking can be limited, especially on busy nights. Arrive a bit early or consider carpooling to ensure you find a convenient spot.

3. Bistro Dansk

LocationAddress: 63 Sherbrook St, Winnipeg, MB R3C 2B2, Canada

Google Maps: Bistro Dansk

Contact DetailsPhone: +1 204-775-5662

Email: [email protected]

Operating HoursMonday Closed

Tuesday 11 AM–2 PM, 4:30–8 PM

Wednesday 11 AM–2 PM, 4:30–8 PM

Thursday 11 AM–2 PM, 4:30–8 PM

Friday 11 AM–2 PM, 4:30–8 PM

Saturday 11 AM–2 PM, 4:30–8 PM

Sunday Closed

Must-order ItemsChicken Salad, Herring Plate, Chicken Schnitzel, Morbradbof, Frikadeller, Veprova, Chicken Livers, Deep Fried Brie or Mozzarella, Kylling, Paprika Chicken, Pollo Alla Childron, Beef Tenderloin, Rainbow Trout, Stuffed Veal Tenderloin
Price$$ (Average)

Bistro Dansk, offering a delectable taste of Denmark since 1977, provides a unique dining experience in Winnipeg. With its authentic Danish dishes served in a homey, paneled dining room, the restaurant has become synonymous with Danish cuisine.

Despite its standing as one of the busiest establishments on our list, patrons willingly endure the wait, attesting to the exceptional dining experience Bistro Dansk provides.

Nestled in a quaint setting, the restaurant exudes charm, creating an intimate ambiance that adds to its allure.

The highlight of Bistro Dansk is undoubtedly its renowned schnitzel, served promptly after cooking to ensure patrons savor the dish at its hot and flavorful best.

For those in search of a culinary journey to Denmark within Winnipeg, Bistro Dansk remains a must-visit destination, where the commitment to quality and authenticity has made it a culinary institution for over four decades.

Pro Tip: 

This cozy restaurant has a warm ambiance, making it perfect for intimate gatherings. Opt for a mid-week visit for a quieter experience.

4. Hy’s Steakhouse and Cocktail Bar

LocationAddress: 1 Lombard Ave, Winnipeg, MB R3B 0X3, Canada

Google Maps: Hy's Steakhouse and Cocktail Bar

Contact DetailsPhone: +1 204-942-1000
Operating HoursMonday 4–10 PM

Tuesday 11:30 AM–10 PM

Wednesday 11:30 AM–10 PM

Thursday 11:30 AM–10 PM

Friday 11:30 AM–11 PM

Saturday 3–11 PM

Sunday 3–9 PM

Must-order ItemsJumbo Prawn Cocktail, Fresh Oysters, Zucchini Carpaccio, Black & Blue Ahi Tuna, Crab Cake, Porterhouse, Bone-In Rib Steak, Steak Neptune, Beef Wellington, Steak Tartare, Tuscan Pasta, Slow-Roasted Half Free-Range Chicken
Price$$$ (Expensive)

Hy’s, tracing its roots back to 1958, stands as an upscale steakhouse in Winnipeg celebrated for its top-notch steaks and classic cocktails.

Renowned as one of the city’s 5-star high-end restaurants, Hy’s is the quintessential go-to destination for special occasions.

While it leans towards the pricier side, the restaurant’s impeccable service and exceptional food make it a worthy investment.

Hy’s commitment to excellence is evident in its meticulous attention to detail, both in the culinary offerings and the service provided. An immersive experience awaits patrons as some menu items are crafted in front of them, adding a unique touch to the dining affair.

Locals and visitors alike highly recommend Hy’s. It’s a testament to its enduring reputation for delivering an unparalleled dining experience.

It’s also where the fusion of sophistication, culinary mastery, and a touch of spectacle defines the essence of this esteemed establishment.

Pro Tip: 

Hy’s is known for its upscale atmosphere. If you’re planning a special occasion, mention it when making a reservation for a potential surprise or treat.

5. Silver Heights Restaurant

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

Google Maps: Silver Heights Restaurant

Contact DetailsPhone: +1 204-889-7246

Email: [email protected]

Operating HoursMonday 11 AM–12 AM

Tuesday 11 AM–12 AM

Wednesday 11 AM–12 AM

Thursday 11 AM–12 AM

Friday 11 AM–2 AM

Saturday 11 AM–2 AM

Sunday Closed

Must-order ItemsSweet Potato Fries, Cyprus Calamari, Traditional Poutine, Saucy St. Jame-er, Caesar Salad, Chef's Haddock, Baby Back Ribs, Veal Cutlet, Certified Angus Steak Sandwich, Angus Cheeseburger, Western Denver, Quesadilla, The Apollo
Price$$ (Average)

Since 1957, Silver Heights Restaurant has been a stalwart in Winnipeg. It offers a warm and inviting environment for those seeking comfort food. 

This establishment has carved its niche as the go-to spot for hearty breakfasts and classic diner fare. However, Silver Heights’ claim to fame is also its impeccable BBQ ribs, which are a favorite among Winnipeggers. 

Renowned for their rich flavor and tenderness, these ribs stand out as a must-try culinary delight. The attention to detail extends to the sides, with perfectly cooked potatoes and vegetables that impeccably complement the star dish.

Beyond the delectable cuisine, Silver Heights enhances the dining experience by fostering a lively atmosphere. The restaurant hosts interactive games that create an animated ambiance that contributes to its vibrant charm.

Overall, nearly every dish at Silver Heights Restaurant receives high praise, and this makes choosing any item from the menu a delightful dilemma. It also ensures a satisfying and regret-free dining experience.

Pro Tip: 

Silver Heights is family-friendly, but weekends can get busy. If you have kids, plan an early dinner to avoid the crowds.

6. Ichiban Japanese Steakhouse & Pub

LocationAddress: 189 Carlton St, Winnipeg, MB R3C 3H7, Canada

Google Maps: Ichiban Japanese Steak House

Contact DetailsPhone: +1 204 925-7400

Email: [email protected]

Operating HoursSunday 5–9 PM

Monday Closed

Tuesday Closed

Wednesday 5–9 PM

Thursday 5–9 PM

Friday 5–9:30 PM

Saturday 5–9:30 PM

Must-order ItemsSushi Tacos, Yakitori, Tempura, Sunomono Salad, Filet Mignon & Lobster, Teriyaki Chicken, Hand Rolls, Salmon Roll, Cucumber Roll, Dragon Eye, Rhino, Fuji Volcano, Midori
Price$$$ (Expensive)

Since its inception in the mid-1970s, Ichiban has been a staple in delighting patrons with its teppanyaki-style Japanese cuisine.

Focused on the interactive teppanyaki experience, the restaurant has become a favored destination for families and groups.

While teppanyaki takes center stage at Ichiban, the menu also features a range of other traditional Japanese delights. This diverse offering caters to a broad spectrum of tastes, ensuring there’s something for everyone.

What sets Ichiban apart is not just the cuisine but the captivating performance by the chefs. Their fantastic and charming culinary skills add an extra layer of enjoyment to the dining experience.

Amidst this lively showcase, the atmosphere remains pleasantly intimate, making Ichiban an ideal choice for those seeking a peaceful yet engaging dinner. 

Pro Tip: 

For a unique dining experience, try sitting at the hibachi grill tables. It’s entertaining to watch the chefs prepare your meal right in front of you.

7. Dairi-Wip

LocationAddress: 383 Marion St, Winnipeg, MB R2H 0V4, Canada

Google Maps: Dairi-Wip

Contact DetailsPhone: +1 204-233-5144
Operating HoursMonday 11 AM–9 PM

Tuesday 11 AM–10 PM

Wednesday 11 AM–10 PM

Thursday 11 AM–10 PM

Friday 11 AM–10 PM

Saturday 11 AM–10 PM

Sunday 11 AM–9 PM

Must-order ItemsDouble Fat Boy, Cheese Burger, Chilli Burger in a Bowl, Hot Dog, Double Cheese Dog, French Fries, Fries with Chilli, Poutine, Fries with Gravy, Fries with Chilli and Cheese
Price$ (Cheap)

Dairi-Wip, an iconic drive-in since 1958, captures the essence of classic Americana in Winnipeg. Renowned for its burgers, fries, and milkshakes, Dairi-Wip has become a beloved staple in the city’s culinary landscape.

As an affordable, old-school burger joint, Dairi-Wip’s drive-in concept harks back to a bygone era, making it a nostalgic and accessible choice for locals. 

The restaurant’s commitment to quality is evident in its use of beefy patties, adding a satisfying depth of flavor to its offerings.

Its bestseller, the Fat Boy, is highly recommended. From the beefy patties to the perfectly cooked accompaniments, every element is executed perfectly. 

Pro Tip: 

Dairi-Wip is a classic drive-in experience. Bring cash for a quick and easy transaction at the drive-thru.

8. Gunn’s Bakery

LocationAddress: 247 Selkirk Ave, Winnipeg, MB R2W 2L5, Canada

Google Maps: Gunn's Bakery

Contact DetailsPhone: +1 204-582-2364

Email: [email protected]

Operating HoursMonday 7:30 AM–4 PM

Tuesday 7:30 AM–4 PM

Wednesday 7:30 AM–4 PM

Thursday 7:30 AM–5 PM

Friday 7:30 AM–5 PM

Saturday 7 AM–3 PM

Sunday Closed

Must-order ItemsNew York Bagel, Boston Bagel, Cheese & Onion Bagel, Kaiser Bun, Panini Bun, Pumpernickel, Bowties, Rugelach, Apple Cranberry Strudel, Chocolate Chocolate Chip Cake, Strawberry Short Cake, Chocolate Chip Cookie, Gingersnap Cookie
Price$$ (Average)

Gunn’s Bakery has been the city’s cherished source of Jewish and Eastern European baked goods for decades. Local favorites include the renowned bagels, rye bread, and an array of delectable pastries.

Beyond being a purveyor of delicious baked goods, Gunn’s Bakery is committed to serving a diverse clientele, accommodating those with dietary restrictions, especially catering to diabetic individuals. 

The welcoming atmosphere extends from the staff to the owner and creates a warm and inviting environment for patrons. 

This commitment to hospitality has been a hallmark of Gunn’s Bakery since its establishment in the 1930s. This solidifies its status as one of the oldest eateries in Winnipeg featured on this list. 

Gunn’s Bakery continues to be a cherished destination, not only for its delightful baked treats but for the enduring sense of community and inclusivity it has fostered over the decades.

Pro Tip: 

Gunn’s Bakery is a local gem for baked goods. Arrive early to have the best selection, as they may sell out of popular items later in the day.

9. Myer’s Delicatessen

LocationAddress: 1842 Grant Ave, Winnipeg, MB R3N 0N4, Canada

Google Maps: Myer's Delicatessen

Contact DetailsPhone: +1 204-489-6310

Email: [email protected]

Operating HoursMonday Closed

Tuesday 10 AM–5 PM

Wednesday 10 AM–5 PM

Thursday 10 AM–5 PM

Friday 10 AM–5 PM

Saturday 10 AM–5 PM

Sunday Closed

Must-order ItemsMontreal Smoked Meat, Corned Beef, Roast Beef, Roast Turkey, Smoked Ham, Hungarian, Coney Island, Tuna Melt, Reuben, Turkey Pesto, Spicy Scarlett, Beef Dip, Chicken Vegetable, Curried Turkey with Jasmine Rice, Greek Pasta
Price$$ (Average)

Founded in 1958, Myer’s Delicatessen is a haven for authentic Jewish deli dishes in Winnipeg. Renowned for its legendary smoked meat sandwiches, Myer’s has secured its place as a local culinary institution.

It stands out for serving the city’s best sandwiches, boasting a commitment to freshness that permeates every bite. 

The owner is known for his warmth and accommodation. He greets patrons with a friendly smile and engages in quick, personable conversations, fostering a welcoming environment. 

And as a family-owned establishment, Myer’s Delicatessen embodies a sense of tradition and community.

Adding to the charm, the staff at Myer’s goes the extra mile by offering patrons complimentary water bottles and cookies. It’s genuinely a gesture that contributes to the restaurant’s exceptional hospitality. 

With a vintage and calm ambiance, Myer’s Delicatessen satisfies culinary cravings and offers a nostalgic and enjoyable dining experience that keeps patrons coming back for more.

Pro Tip: 

Myers Delicatessen is known for its deli sandwiches. Consider ordering ahead if you’re in a hurry to avoid a wait during peak lunch hours.

10. The Original Pancake House


• 2220 McGillivray Blvd, Winnipeg, MB R3Y 1N8, Canada

• 1 Forks Market Rd, Winnipeg, MB R3C 4L9, Canada

• 1445 Portage Ave, Winnipeg, MB R3G 3P4, Canada

Google Maps:

2220 McGillivray Blvd

1 Forks Market Rd

1445 Portage Ave

Contact DetailsPhone:

• 2220 McGillivray Blvd : +1 204-489-2885

• 1 Forks Market Rd : +1 204-947-5077

• 1445 Portage Ave : +1 204-775-9035

Email: [email protected]

Operating HoursMonday 7:30 AM–8 PM

Tuesday 7:30 AM–8 PM

Wednesday 7:30 AM–8 PM

Thursday 7:30 AM–8 PM

Friday 7:30 AM–8 PM

Saturday 7:30 AM–8 PM

Sunday 8 AM–8 PM

Must-order ItemsGiant Apple Pancake, Chocolate Banana Pancake, Classic Benny, Manitoba Scramble, Chorizo & Bacon Omelette, Pierogi Breakfast, The Original, Berry French Toast, Chicken Caesar Wrap, Crispy Chicken Sandwich, Champion Burger
Price$$ (Average)

With a history dating back to 1953, The Original Pancake House has been a breakfast staple in Winnipeg. Situated initially on Pembina Highway, the restaurant’s immense popularity prompted the opening of additional locations across the city.

What distinguishes The Original Pancake House is its commitment to crafting breakfast classics from fresh batters prepared in their commissary. 

Each item offers a unique and delightful twist, from buttermilk pancakes to crepes, oven-baked pancakes, and waffles.

Catering to families, the restaurant is particularly beloved by children who appreciate the kid-friendly atmosphere. 

However, parents find equal joy in the diverse menu and welcoming ambiance, making The Original Pancake House a cherished destination for breakfast enthusiasts of all ages.

Pro Tip: 

Weekend mornings can be busy, so if you’re craving a leisurely breakfast, aim for a weekday visit to avoid the crowds.

11. Red Top Drive Inn

LocationAddress: 219 St Mary's Rd, Winnipeg, MB R2H 1J2, Canada

Google Maps: Red Top Drive Inn

Contact DetailsPhone: +1 204-233-7943
Operating HoursMonday 8 AM–8 PM

Tuesday 8 AM–8 PM

Wednesday 8 AM–8 PM

Thursday 8 AM–8 PM

Friday 8 AM–9 PM

Saturday 8 AM–9 PM

Sunday 9 AM–2 PM

Must-order ItemsTop Burger, Cheez-Burger, Chicken Burger, The Mayor, Monster Burger, BBQ Chicken Burger, Chili Dog, Deluxe Dog, Chicken Dinner, Chicken Finger Plate, Beef and Lamb Gyro, Triple Decker, Roast Beef, House Salad
Price$ (Cheap)

Established in 1960, Red Top Drive Inn emerged as a classic burger haven with carhop service, offering a delightful slice of retro nostalgia in the heart of Winnipeg.

It’s not just another burger joint; it’s a destination that immerses patrons in a proper dinner experience, cultivating a laid-back ambiance perfect for a relaxed meal.

At Red Top, the staff goes beyond friendly – they’re your guides to a memorable dining experience, ensuring prompt and helpful service. The food is not just awesome; it’s a budget-friendly culinary adventure, providing excellent value for money.

With portions that are as generous as the service is friendly, Red Top Drive Inn stands out as more than just a restaurant. It’s an engaging and satisfying journey into classic Americana, inviting patrons to savor every moment and every bite.

Pro Tip: 

Bring a nostalgic vibe by enjoying your meal in your car or at one of the outdoor tables.

12. Salisbury House


• 177 Lombard Ave, Winnipeg, MB R3B 0W5, Canada

• 787 Leila Ave, Winnipeg, MB R2V 3J7, Canada

• 759 Pembina Hwy, Winnipeg, MB R3M 2L9, Canada

• 255 St Anne's Rd, Winnipeg, MB R2M 3A5, Canada

• 3315 Portage Ave, Winnipeg, MB R3K 0W7, Canada

• 1277 Henderson Hwy, Winnipeg, MB R2G 1M3, Canada

• 1570 Regent Ave W, Winnipeg, MB R2C 3B4, Canada

Google Maps:

177 Lombard Ave

787 Leila Ave

759 Pembina Hwy

255 St Anne's Rd

3315 Portage Ave

1277 Henderson Hwy

1570 Regent Ave W

Contact DetailsPhone:

• 177 Lombard Ave : +1 204-289-4320

• 787 Leila Ave : +1 204-694-0931

• 759 Pembina Hwy : +1 204-453-6404

• 255 St Anne's Rd : +1 204-255-2823

• 3315 Portage Ave : +1 204-889-3156

• 1277 Henderson Hwy : +1 204-661-2374

• 1570 Regent Ave W : +1 204-661-6539

Operating HoursMonday 6 AM–10 PM

Tuesday 6 AM–10 PM

Wednesday 6 AM–10 PM

Thursday 6 AM–10 PM

Friday 6 AM–10 PM

Saturday 6 AM–10 PM

Sunday 6 AM–10 PM

Must-order ItemsSilver pancakes & Sausage, Silver Salisbury Steak, Silver Liver & Onions, Silver Lemon Herb Chicken Dinner, Classic Perogy, Buffalo Chicken Perogy, Sals Poutine, Three Buttermilk Pancakes & Meat, Nip Platter, Homestyle Breakfast
Price$ (Cheap)

Salisbury House, affectionately known as “Sals,” has been offering a taste of hometown comfort since 1931. Renowned for its burgers and milkshakes, Sals has become a beloved restaurant chain based in Winnipeg.

The dining experience at Sals is marked by spectacular excellence, from the attentive servers to the delectable offerings.

Whether you’re savoring their famous burgers or indulging in a hearty breakfast, Salisbury House remains a cherished destination, embodying the essence of local comfort and culinary excellence for over nine decades.

Pro Tip: 

Known for its iconic “Nip” burgers, Salisbury House can get crowded during lunch. Visit during off-peak hours for a more relaxed dining experience.