Diner déjà vu: A look back at Winnipeg’s nostalgia-packed, burger-loving eateries of days gone by

A slice of '50s nostalgia is on the menu at Dreamland Diner on Portage Avenue. (Scott Andersson/CTV News Winnipeg)

Growing up in Winnipeg, brothers Ravi and Kevin Ramberran recall a certain kind of eatery that stacked up in the Winnipeg restaurant scene, much like the short stacks of buttermilk pancakes they served at their vinyl booths, the faint sound of Elvis Presley crooning through the air.

“Diners were a little bit more ubiquitous in Winnipeg and just outside of the city,” Kevin told CTV News Winnipeg.

“There’s still some of those kicking around, which is awesome, but there’s a lot less now than there used to be.”

Outside of the perimeter, diners hold a certain pop culture fascination—from the frosty milkshakes with three straws at Pop’s Chock-Lit Shoppe in “Archie Comics” to the jukebox-scored Arnold’s Drive-In in “Happy Days” to the damn fine coffee at Double R Diner in “Twin Peaks.”

For the Ramberrans, their diner touchstone was in Hill Valley circa 1955.

“(My brother) loves Back to the Future. There’s a great diner scene,” Kevin said.

It’s a dining tradition steeped in nostalgia—one the brothers were eager to reintroduce to the Winnipeg food scene when a space opened up in 2023 along Portage Avenue in the heart of St. James.

“We wanted to bring a bit more of the kid-like joy that you might get from going to a diner and having a good time,” Kevin explained.

That’s how Dreamland Diner was, well, dreamt up, earning its name from a 1958 Everly Brothers song.

It wasn’t’ the Ramberrans’ first resto rodeo. They own nearby St. James Burger and Chip Co., and Ravi heads up Four Crowns Restaurant along McPhillips Street.

This project called for a 1950s Americana makeover, bringing in black and white checkerboard floors, the type of deep vinyl booths you sink into to enjoy a tall burger with a healthy mound of fries at a chrome-sided table, and retro televisions playing 1950s cartoons and ads. A whole gallery wall is devoted to Marilyn Monroe pictures, subway grate and all.

The menu is packed with diner favourites—banana splits, smash burgers, fries, and milkshakes. Saddle shoes and poodle skirts are not the mandatory dress code for patrons, but always encouraged.

Grease cosplay aside, Kevin hopes Dreamland serves as a homey return to more casual dining and the city’s earliest roots.

“Winnipeg is such a funny city to have such a diner history, given that we have such a huge history of rail infrastructure. We were such a hub for that.”

Tracing Winnipeg’s history of diners, drive-ins and dives

It’s true, Winnipeg comes by its diner-rich history honestly.

Kimberley Moore should know. She wrote the book on Manitoba’s food landscape, quite literally, as co-author of “mmm…Manitoba: The Stories Behind the Foods We Eat.”

According to Moore, diners evolved from several dining traditions—be it night lunch carts serving ready-made food to shift workers or, to Kevin’s point, from train dining cars. Rail cars were plucked off the tracks in the States and put down in the streets, serving the hungry masses at cylindrical bars that could maximize their limited square footage. Deep fryers and grills churned out fast casual food at affordable prices, often providing around-the-clock service.

Moore delved deeper into the history of Winnipeg’s diner scene while researching the book, only to discover the definition of diners could serve as a catch-all for drive-ins, lunch counters, cafés, and grills.

“In Winnipeg, there’s definitely a boom in diners at the end of the 1950s,” she said.

“Beginning in 1958, we start to see more diners and drive-ins, but this actually begins much sooner than we kind of associate with that typical mid-century diner. So in the 1930s, what begins to happen is more and more people start to work downtown.”

This created a boon of lunch counters on Portage and Main, as well as the first Salisbury House on Fort Street, which was established in the 1930s as a small diner with a grill and a few stools at the counter.

From there, diner popularity expanded alongside the city’s geography. As folks began to move to the suburbs, the family-friendly eateries followed them to the city’s outskirts. They also popped up alongside industrial and manufacturing areas, feeding hungry workers opting to forgo the brown bag.

Today, the influence of the mid-century diner can be found in most fast-food restaurants, Moore added. Think A&W, with its countless black-and-white photos reminding diners at its hundreds of locations across North America of a simpler time when their mugs of root beer were served frosted and on a tray, right to your car window. Bonus retro points if the server was wearing roller skates.

Moore isn’t quite sure what’s behind the diner’s staying power and our collective fascination with their vinyl-covered tropes. She suspects a certain ad exec-boosted nostalgia lies at its heart.

“It’s equal parts marketing and longing for a past that never really existed, and I think that it is very personal,” she said.

“One of the things I always notice about going to Salisbury House, for example, is that you always overhear people telling the wait staff how much they love the Salisbury House and how long they’ve been coming to the Salisbury House for, so I think part of it is consistency and part of it is a sense of homefulness, especially in Winnipeg, where we have these institutions that kind of stay the same.”

For Ramberran, the diner tradition extends beyond nostalgia to a setting that makes connection feel as natural as sharing a milkshake and a side of fries.

“At its core, I think for people it is about gathering and establishing connections with the people close to them,” he said.

“Diners have historically made people feel a little more comfortable and a little more relaxed when they’re enjoying their food. It allows them to feel like they’re at home and opening up to their friends and family a little easier.”