Do you ever wish you could travel back in time and experience what life was like in Canada decades ago? We can’t turn back the clock, but we can certainly transport ourselves by visiting these 10 Canadian dining destinations from coast to coast. Whether it’s historic buildings, vintage decor or classic menu items, each restaurant will send you on a journey to another era in Canadian history.
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YellowBelly
YellowBelly Brewery (St. John’s, Newfoundland and Labrador)
YellowBelly Brewery is housed in a historic building at the intersection of George and Water Streets in downtown St. John’s. First built in the 18th century and then reconstructed after the fire of 1846, it features multiple fireplaces, original stone and brickwork, wide plank flooring and spaces for dining, meeting and celebrating. It’s also home to the UnderBelly, Newfoundland’s only speakeasy and one of the oldest rooms in North America.
Discover Halifax
The Narrows Public House (Halifax, Nova Scotia)
A traditional Nova Scotian public house, The Narrows is located on Gottingen Stret in Halifax’s north end, directly across from the Navy Museum. Operating out of the restored H.R. Silver House, a heritage home from 1896, the pub features authentic Nova Scotian dishes, plus there are inn-style accommodations upstairs. The original owner of the building was connected to rum-running and the original Bluenose Fishermen’s Race, among other events in Maritime history.
Water Prince Corner Shop
Water Prince Corner Shop (Charlottetown, Prince Edward Island)
The Water Prince Corner Shop has served only the freshest fish and seafood direct from Prince Edward Island’s fishermen for more than three decades. Tuck into a table in the dining room for lobster, fish and chips or their famous seafood chowder. The building itself, located in Olde Charlottetown, has been a part of the city’s history since 1950 when it was founded as the Prince Street Grocery.
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Fredericton Tourism
The King’s Head Inn (Prince William, New Brunswick)
The King’s Head Inn, located at the heart of the award-winning Kings Landing attraction in the Fredericton Capital Region, will immediately transport you to the 1800s. After exploring the historic settlement, stop for a pint of ale at the restaurant’s English-style pub accompanied by live music. If you’re looking for a truly unique experience, indulge in a traditional loyalist feast served by costumed waitstaff and strolling performers.
Susan Moss
Gibeau Orange Julep (Montreal, Quebec)
The history of Gibeau Orange Julep goes all the way back to 1932, but the current orange sphere — the largest in the world — was built in 1964. The 60-foot “Big Orange” is a slice of mid-century life, still serving their signature beverage alongside burgers, hot dogs, poutine and sandwiches. In the warmer months, this drive-in restaurant attracts vintage car enthusiasts each evening, making it feel even more like you’ve stepped through a portal to the 1960s.
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Old Mill Toronto
The Old Mill (Toronto, Ontario)
The Old Mill has been a part of Toronto’s history since the early 1900s. The Old Mill Tea Garden opened in 1914, on the same day that World War I began, and became a community hub. In 1919, the Print Room was built, becoming a destination for fine dining and dancing, a tradition that has continued. Roast beef dinners and Sunday brunches made it a favourite for family gatherings in the 1930s and 1940s. In the decades after surviving Hurricane Hazel in 1954, they added banquet rooms, a chapel and event spaces. It stands as a landmark where people gather for afternoon tea, weddings and special occasions.
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Peg City Grub
The Oval Room Brasserie (Winnipeg, Manitoba)
Formerly known as the Palm Lounge, the Oval Room Brasserie is located in the majestic Fort Garry Hotel, a downtown Winnipeg landmark since 1913. Reopened in 2021 following an extensive restoration to its original grandeur, including the intricate plaster work on the ceiling that had been damaged due to a burst sprinkler, walking into this place is like stepping back into a time when it was the place to see and be seen in the city.
Caesar’s Steakhouse
Caesar’s Steakhouse (Calgary, Alberta)
A Calgary institution since 1972, the original location of Caesar’s Steakhouse was formerly a downtown print shop. They’ve always aimed to provide what they describe as “a luxurious experience fit for an emperor,” with luxe interior decor like dark woods, burgundy leather, red carpeting and majestic white columns. With a menu centred on the finest Alberta beef seasoned with their signature steak spice, it’s where locals go to celebrate anniversaries, birthdays and even business deals.
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Mount Pleasant Vintage & Provisions
Mount Pleasant Vintage & Provisions (Vancouver, British Columbia)
This charming, 70s-inspired cocktail bar and grill is located in a restored heritage home with an interesting history. Mount Pleasant Vintage & Provisions opened in the 1901-built Coulter House, primarily known as the 6th Avenue Grocery until the late 1970s. The building remained empty for decades and following a restoration, it is now part of a mixed-use development. They’ve embraced the 70s vibe with retro-style lighting fixtures, furnishings, and a menu featuring boozy slushies, charcoal-grilled meats and even tater tots.
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Michael Cross
Sourdough Saloon (Dawson City, Yukon)
Dawson City was at the centre of the Klondike Gold Rush in the late 1890s, and the Sourdough Saloon celebrates that era. Designed with swinging doors and other historic decor, it is most famously known as the home of the Sourtoe Cocktail Club. A storied rite of passage for visitors from around the world, the tradition requires drinking a cocktail with a rather macabre garnish: a mummified, severed human toe. Never fear, you don’t actually ingest the toe. Your lips just have to touch it to complete the challenge.
Osteria Rialto
Osteria Rialto (Toronto, Ontario)
Housed within the 100-year old Paradise Theatre, lives the newly renovated Osteria Rialto. This full-service Italian restaurant is a welcomed addition to the Bloor West Village in Toronto. The theatre itself is steeped in local history centered around the performing arts since 1910. In addition to Osteria Rialto, the theatre boasts a stunning café, rooftop bar, wine shop and a 220-seat theatre space. If you’re looking for a night out on the town, Osteria Rialto should be your first stop.