From famous flapper pie to Stampede-worthy cowboy boots, I went in search of Calgary’s old-school cool

Sadly, they had sold out. The waitress instructed me to return the next day — early if I wanted a slice. I mentioned that I wanted to write about their famous pie, and she laughed but told me to come back and they’d fix me up.

To my surprise, a whole pie was waiting for me the next morning. As I dug into a delicious slice (the more reasonable portion I talked them down to), Blackfoot’s baker of 14 years, Adnan Elkassem, explained that getting the topping that high was a delicate process.

“Whip the meringue too much or too little and it won’t rise, and it has to sit exactly the right amount of time before baking. It takes 24 hours to make flapper pie,” Elkassem says. “So we can’t just make more on demand.” Too full to sample more from the menu — which features true diner delicacies like Trucker’s Breakfast, patty melts and beef dips — I promised I’d be back someday to try them. 

I’ve visited Calgary numerous times, eating at fabulous fine-dining restaurants such as Major Tom, and checking out the newest and most exciting attractions. On this trip, however, I wanted to see the places that had barely changed in decades, the ones untouched by oil and gas money, just serving locals exactly what they want.

I asked friends for recommendations and found myself exploring neighbourhoods I never even knew existed, such as Bridgeland, a small, walkable area northeast of downtown Calgary. It’s known for its independently owned shops, including the original location of Lukes Drug Mart, a family-run more-than-a-pharmacy with a penchant for supporting local brands, artists and the community.

When Gareth Lukes took over the pharmacy, which his grandfather started in 1951, he evolved the business to include a gorgeous coffee bar and a record store. It’s also become a hip spot for gourmet soft serve, which comes in Lukes’ signature Milk+ flavour, made with sweetened condensed milk, and in limited-edition flavours developed in collaboration with other Calgary businesses.

For quintessential Calgary shopping, I paid a visit to the Alberta Boot Co., where every boot has been crafted by hand since it opened in 1978. Shoppers can glimpse the meticulous process for themselves through the huge window overlooking their workshop. I splurged on ankle-high leather boots that barely whispered “Western wear,” but traditionalists can find a wide array of cowboy boots worthy of the Stampede, celebrities and visiting British royals alike — the store has made footwear for them all.

My next stop took me to the most fun I’d had at any fine-dining establishment in years: the downtown institution known as Caesar’s Steakhouse and Cocktail Bar. Walking in there felt like stepping into Rat Pack-era Las Vegas: The restaurant oozes old-fashioned glamour, seeming not to have changed an awful lot since opening in 1972.

The lighting is low, the servers are suited up, and the menu is all about quality steaks (only Alberta beef, of course) and unforgettable sides — the onion rings came doughnut-sized. My companion and I opted for tableside-prepared Caesar salad, made from scratch and done right, followed by perfectly flambéed steak Diane, with cherries jubilee for dessert. We effectively enjoyed dinner and a show.

My tour of Calgary’s old-school cool felt like just a small taste of the authentic gems the city has to offer. The spots I mentioned were the highlights, but I also wandered Chinatown with a tour guide pointing out historic spots, browsed vintage stores in Inglewood, ate a massive, made-to-order burger at the nostalgic Boogie’s (slogan: “Slangin’ Burgs Since ’69”), and chatted with locals who shared more places I must visit next time.

As I promised over that slice of flapper pie, I’ll be back to try them.

Lola Augustine Brown travelled as a guest of Tourism Calgary, which did not review or approve this article.