The Century Club: Montreal's Oldest Businesses Still Standing Today

This story originally appeared in a special edition The Main x URBANIA Micromag. Read the full collection here.

The steamé, the bagel, the hat trick—so woven into the texture of Montreal life that they barely register as belonging to anyone. Maybe that’s because it comes from places that have been around for so long that their impact on the city is timeless.

Take Henri Henri hat shop owner, Jean Maurice Lefebvre, who in 1947 started walking onto the ice at the Montreal Forum to hand a brand-new hat to any player from any team who scored three goals in a game. The expression "hat trick" traces back to that gesture, to a shop on Sainte-Catherine that opened in 1932 and is still open today. The tradition still stands for any Habs player who completes one. Generations of Montrealers have used that phrase, possibly without ever knowing where it came from.

What would it take to kill them? Probably less than you'd think. A rent hike, a fire, a pandemic, a bad year. Most of them have faced at least one of these and are still here. But for now, these are the businesses that haven’t merely withstood the test of time—they aced it.

The pool room that has no pool tables

Filipoff Dakov, a Bulgarian immigrant, opened the Montreal Pool Room in 1912 on Saint-Laurent Boulevard on the edge of what would become the city's Red Light District. Nobody quite remembers when the pool tables disappeared, sometime in the seventies, but the steamé hasn't changed. Cash only, counter seating, and three OG employees who've been coming in to work for close to thirty years.

The Goulakos family took it over in 2018, and Spiro Goulakos has been managing the restaurant since 2021, two years after his father Socrates bought the place. Spiro is clear about where the credit belongs. "The staff are really the heartbeat of the place," he says of those long-timers. "Any idea I come up with has to pass through them." The formula is simple: consistency, nothing fancy.

"There's nothing special about our place," Spiro says. "It's just bare bones, and it works."

Hand rolled since 1919

Isadore Shlafman arrived from Russia and opened the first bagel bakery in Montreal in 1919, and with it one of the city’s most iconic food identities. Automation reshaped bread-making in many ways, but never touched Fairmount’s old country ways, as the dough is still hand-rolled and baked in wood-fired ovens. The recipe hasn’t changed, but founder Isadore isn’t too stubborn to listen to customers’ needs. The sesame bagel exists because an older customer kept complaining about poppy seeds in his dentures.

His grandchildren Irwin and Rhonda have been running it since their twenties. "Everyone else around us has changed," Irwin says. "We have remained the same."

"We'd have to be cloned and reborn," Irwin says, when asked what it would take to still be here in another hundred years. He laughs. "We're the third generation, and that's already rare. We'll see."

Across the street, they’ve opened a café with a wall of photographs going back to their grandparents, pictures of the employees who showed up to work at the shop from the day they immigrated, raised families, and built lives.

Until COVID imposed a curfew in 2020, Fairmount Bagel had never had a lock on its door. Not since 1980, when the original wooden door was replaced and the carpenter asked where to drill. Irwin's father said don't bother—they were already open twenty-four hours, seven days a week.

Size matters

Max and Jenny Grover opened a men's clothing store in Verdun in 1925. Their grandson, Kenny, studied accounting at McGill, hated the desk job that followed, and came to help his father over the holidays. Come January, he never left. He watched eight other menswear stores on Wellington close and figured out why his kept surviving: the bigger sizes always sold out first. He doubled down on big and tall, bought the building, kept it going, and does every alteration in-house. "I will not let someone go out looking like they're wearing their father's pants," Kenny says. "When things are really bad and other companies are down 30%, we're never down 30%."

Kenny thinks of it as a pyramid, each generation laying a stronger foundation than the last. His son Jacob is now four years in, fourth generation, handling e-commerce and building a social media presence that has customers walking in and saying, "You're the guy from the videos."

Jacob’s take: "I hope my generation isn't bringing us closer to the top. I hope we're strengthening the foundation so there's room for many more generations to build on it."