Winnipeg’s Oldest Restaurants

A Taste of History

At Oscar’s Deli, corned beef is still stacked between slices of Winnipeg rye in a business that began on Main Street in 1929. Two years later, Salisbury House opened an all-night café with ten counter seats on Fort Street. Neither original room survives, but both names remain in use.

Other restaurants carried their menus across the city. Good Earth moved from the North End to several addresses before reaching Portage Avenue in St. James. Rae & Jerry’s began downtown before opening its present steakhouse near Polo Park in 1957.

The dates below mark the earliest documented opening of each restaurant business, rather than the opening of its present building. Relocations, name changes, and interruptions are explained in the individual entries. Restaurants sharing an opening year are arranged alphabetically when a more precise date could not be confirmed.

Winnipeg Restaurants That Continue Today

Oscar’s Delicatessen (1929)

Oscar Berman opened Oscar’s Delicatessen on Main Street in 1929. The business later passed through several owners before expanding to Hargrave Street in 1982. The original Main Street restaurant closed during the mid-1990s, but the Hargrave location continued under the Oscar’s name.

Corned beef and pastrami remain central to the menu, served on thick slices of Winnipeg rye with pickles and coleslaw. The downtown deli continues operating at 175 Hargrave Street.

Salisbury House (1931)

Ralph Erwin opened the first Salisbury House on Fort Street in 1931. The all-night café seated ten customers at its counter and served a hamburger Erwin renamed the “Nip,” a term still used on Salisbury House menus.

Additional restaurants appeared across Winnipeg within a few years. Although the Fort Street café is gone, Salisbury House continues as a Manitoba restaurant chain serving Nips, breakfasts, pancakes, and diner meals at locations throughout the city.

Rae & Jerry’s Steak House (1947)

John Rae and Jerry Hemsworth founded their restaurant on Kennedy Street in 1947. They later moved to Portage Avenue near Langside Street before opening the present Rae & Jerry’s building at 1405 Portage Avenue in July 1957.

The purpose-built steakhouse retains much of its original mid-century interior, including its red seating, dark wall panels, lounge, and roadside neon sign. New owners took over in 2024 and kept the restaurant’s established name, menu, and dining-room design.

Good Earth Restaurant (1952)

Bill Wong opened the Good Earth Chop Suey House on Main Street in 1952. The restaurant subsequently operated on Portage Avenue downtown and on Osborne Street before moving to its present address at 1849 Portage Avenue.

Good Earth serves the Chinese Canadian dishes associated with its long history, including combination dinners, egg foo yong, fried rice, and breaded meats. Its weekday lunch buffet has also remained a regular draw at the St. James dining room.

Silver Heights Restaurant (June 1957)

Anthony Siwicki Sr. and three partners opened Silver Heights Restaurant at 2169 Portage Avenue in June 1957. What began as a coffee shop expanded into a dining room, lounge, and neighbourhood bar as adjoining space became available.

Members of the Siwicki family continue to operate the restaurant. Barbecued ribs became one of its best-known meals, while the lounge developed a regular programme of sports events and live entertainment.

Dairi-Wip Drive-In (1958)

Dairi-Wip began serving customers on Marion Street in 1958. The current drive-in building and its neon sign date from 1968, preserving the roadside format that became common as Winnipeg expanded after the Second World War.

The family-owned restaurant continues to prepare burgers, hot dogs, fries, milkshakes, and ice cream. Its Fat Boy, topped with Winnipeg-style chili sauce, belongs to a local burger tradition closely associated with the city’s Greek-owned drive-ins.

Hy’s Steakhouse & Cocktail Bar (1958)

Hy Aisenstat opened the Winnipeg Hy’s Steak Loft on Kennedy Street in 1958, three years after establishing the first Hy’s in Calgary. The Winnipeg restaurant remained on Kennedy Street for 46 years.

In 2005, Hy’s moved into the Richardson Building at Portage and Main and adopted the name Hy’s Steakhouse & Cocktail Bar. The dining room continues to serve steaks and tableside Caesar salads within the company’s traditional steakhouse format.

Myer’s Delicatessen (1958)

Myer Ludwig left the family partnership behind Oscar’s Delicatessen and opened Myer’s on Grant Avenue in 1958. The restaurant remains on the same River Heights corner where Ludwig established it.

Its menu centres on hand-cut rye, deli meats, soup, coleslaw, and sandwiches piled with corned beef or pastrami. Later owners retained several recipes connected to Ludwig, including the delicatessen’s longstanding coleslaw.

Original Pancake House (1958)

Wally Guberman opened Winnipeg’s first Original Pancake House on Pembina Highway in 1958. The restaurant attracted families and university students, particularly when its late hours allowed customers to order pancakes well into the night.

The Winnipeg-owned business later expanded to additional locations. Its menus continue to include buttermilk pancakes, crêpes, waffles, and the baked Giant Apple Pancake associated with the restaurant since its early years.

VJ’s Drive Inn (1958)

The small restaurant at 170 Main Street opened as Junior’s in 1958. It later became VJ’s Drive Inn, carrying the original burger stand into a new name while remaining across the street from Winnipeg’s Union Station.

VJ’s is closely associated with the Winnipeg Fat Boy: a hamburger topped with chili meat sauce and the usual burger garnishes. Customers order through the window and eat from paper boxes at the outdoor tables beside the restaurant.

Red Top Drive Inn (1960)

Gus Scouras founded the Red Top Drive Inn at 219 St. Mary’s Road in 1960. Members of the Scouras family operated it for decades before the restaurant changed ownership in 2019.

Red Top continues at its original St. Boniface address. Its broad diner menu includes Fat Boys, fried chicken, breakfasts, and hot sandwiches, served in a dining room that grew from Winnipeg’s postwar drive-in culture.

Gondola Pizza (1964)

Gondola Pizza made its first pizza in Winnipeg in 1964 at the corner of Oakenwald Avenue and Pembina Highway. The original restaurant continues to operate at the same site.

The business developed a thin-crust pizza that became its signature product before expanding into other Winnipeg neighbourhoods and communities outside the city. Pasta and rib dinners were added to the menu using recipes developed during the company’s early years.

Winnipeg Restaurants That Have Closed

Kelekis Restaurant (Opened 1946; Closed January 30, 2013)

Chrystomis “Chrys” Kelekis opened Kelekis Restaurant at 1100 Main Street in 1946 after earlier years selling food from a pushcart, confectionery, and takeout business. His six daughters eventually joined the operation and carried it into a second generation.

The restaurant became known for hand-cut fries, hot dogs, burgers, and photographs of the performers and public figures who had visited. The Kelekis family served its final customers on January 30, 2013.

Wagon Wheel Lunch (Opened December 3, 1951; Closed July 13, 2012)

The Wagon Wheel Lunch opened in the Norlyn Building on Hargrave Street on December 3, 1951. Bill Mathez took over in 1958, and later generations of the Mathez family continued running the narrow downtown lunch counter.

The restaurant was particularly known for its clubhouse sandwich, which combined turkey, ham, bacon, cheese, and an egg between slices of toast. Redevelopment of the building brought service to an end on July 13, 2012.

Paddlewheel Restaurant (Opened October 29, 1954; Closed January 24, 2013)

The Paddle Wheel Buffet opened on the sixth floor of the downtown Hudson’s Bay store on October 29, 1954. Its riverboat décor and cafeteria service made lunch at the Bay an event for generations of Winnipeg families.

Later known as the Paddlewheel Restaurant, it served roast dinners, sandwiches, desserts, and its frequently remembered cubes of coloured gelatin. It closed on January 24, 2013, as activity within the downtown department store continued to decline.

Thunderbird Drive-In Restaurant (Opened 1961; Closed 2025)

Brothers Jimmy, John, and Perry Ginakes opened the Thunderbird Drive-In at the corner of McPhillips Street and Jefferson Avenue in 1961. Carhops originally carried orders to customers eating in their vehicles.

The Thunderbird later operated as a conventional restaurant while retaining its association with Winnipeg burgers and drive-in meals. It closed in 2025 after more than six decades, with insufficient parking cited as a problem for the property.