Searing success Celebrating 50 years, Winnipeg's downtown Keg steakhouse takes pride in its endurance By: David Sanderson Posted: 12:00 PM CDT Friday, May. 23, 2025 Last Modified: 1:42 PM CDT Friday, May. 23, 2025 Updates

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The Keg Steakhouse + Bar at 115 Garry St. — commonly referred to as the Garry Street Keg, or simply Garry Street — turns 50 years old in June.

Gord Howard, the owner of Winnipeg’s three Keg restaurants including the downtown locale, intends to mark the milestone in some manner, though he admits it will be difficult to match the goings-on that occurred there 40 summers ago.

Howard was a manager at the Garry Street Keg in June 1985 when his then-supervisor Griffin Tripp suggested they throw a shindig to toast the popular dining spot’s 10th anniversary. The pair arranged to have Garry Street closed to vehicular traffic between Broadway and York Avenue to facilitate a daylong block party featuring live music and free Keg-size victuals. And because George Tidball, the chain’s founder, was flying in from Vancouver to attend, Tripp suggested they present their boss with a gift upon his arrival.

“George was a horseman originally from Alberta, so Griff thought it would be a good idea to get him a commemorative saddle,” Howard says, seated in the attractive 255-seat spot that, since the outset, has boasted brick walls, oak tables and well-situated fireplaces.

One thing led to another, Howard continues, until it was decided that besides a saddle, they would also show up at the airport on horseback, and invite Tidball to accompany them to the restaurant on a ride they brought for him. (Howard credits a server named Cam Weir, the son of ex-Manitoba premier Walter Weir, for securing the necessary steeds at a moment’s notice.)

Howard still isn’t sure how they managed to pull the stunt off considering they didn’t have a permit. However, after clip-clopping along Portage Avenue and ultimately past the Manitoba legislative building, they reached the Keg in time to catch the first set by headliner Rocki Rolletti.

While there have been discussions about a 50th-anniversary staff reunion — minus the mounts — Howard wonders if such an event is even feasible.

“There have been hundreds, probably thousands of Keggers since we opened in ’75, so where would even we have it, it’d be so big,” he says.

“No action’s been taken yet, but we’re definitely thinking about it.”

“There have been hundreds, probably thousands of Keggers since we opened in ’75, so where would even we have it, it’d be so big.”–Gord Howard, on a 50th staff reunion

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Tidball, who died in 2014 at age 83, established the first Keg ’N Cleaver, as the chain was originally billed, in 1971 in North Vancouver. The Garry Street Keg became the seventh Keg franchise when it opened on June 12, 1975, in a one-time livery stable built in 1911 by the Hudson’s Bay Co.

(A same-day ad that ran in the Free Press invited customers to “help yourself to green salad, garbanzo beans, beets, croutons, onions, home-made dressings and sourdough bread — as much as you like, as often as you like” in addition to steak and lobster entrées that started at $4.45.)

Kathryne Grisim, a media strategist and former restaurant critic for the Free Press Community Review newspapers, was a hostess there on Night 1. She figured she had it “made in the shade,” as her job involved chatting with people in a queue that spilled out the door and onto the sidewalk, for which she was paid an hourly salary and a share of tips.

“The staff that came in from Vancouver to help us knew it would be an instant success so there was definitely a buzz that evening. We were a part of a new style of hospitality and everybody was very excited,” Grisim says, recalling that she and her co-workers received a week’s worth of training beforehand, with managers and family members posing as customers.

Grisim says she could never have guessed during her initial shift that the Garry Street Keg would become like family to her, both figuratively and literally.

“I met my husband Doug there along with his mom, two sisters and three brothers, who all worked for the Keg, too. My sister worked there, as well as my son and youngest daughter. I guess the Keg believed nepotism was a positive staff quality.”

Howard was a 21-year-old University of Manitoba student in 1976 when he applied for a position at a Pembina Highway watering hole. While he was still awaiting a response a month later, a friend told him he should drop his resumé off at the Keg, instead. Howard’s response: “What’s a Keg?”

“Garry Street had been open for less than a year when I started there as a bartender/cook. It was definitely hustle-and-bustle and of course the Keg didn’t take reservations then, so come the weekend, it was especially hectic because people would be lined up outside for an hour or so,” he says, showing off a circa-1975 wooden menu board (“Teriyaki, 11 oz. 5.25; Mushrooms for Two .95”) he keeps on a shelf in his office.

Within a couple of years, Howard had graduated to management. He served as the area manager for Winnipeg, then director of quality for the entire company, before moving to Vancouver in the early 1990s to become executive vice-president of operations for Western Canada.

“In 1997 the company was sold to David Eisenstadt, whose dad Hy started Hy’s Steakhouse in Calgary in 1955,” Howard explains.

“We were a part of a new style of hospitality and everybody was very excited.”–Kathryne Grisim

“David told me he had two main strategies. One was to cut corporate overhead, so I was out. The second was to sell restaurants in isolated markets. He asked if I wanted to buy some restaurants and I moved back to Winnipeg that same year.”

It’s true the Garry Street Keg belongs to a chain — as of March 2025, there were 97 Kegs dotting the country; Garry Street has been at its original site the third longest — but Scott Stephen, the local Kegs’ director of operations, says owing to its historic backdrop, Winnipeg’s flagship location has always had the look and feel of a stand-alone space. Heck, he says, there are a raft of Garry Street regulars who’ve never even bothered to set foot in either the St. James (2553 Portage Ave.) or Southside (2034 McGillivray Blvd.) Kegs.

“We get people (at Garry Street) who’ve been coming for 30… 40 years to celebrate special family events,” says Stephen, who caught on at the Keg in 1985, back when it was commonplace for a half-dozen servers to gather at a birthday celebrant’s table to belt out a rousing rendition of The Old Grey Mare (“she ain’t what she used to be”).

“It doesn’t happen as much as it used to, but there have definitely been nights when a guy has proposed to his girlfriend by asking us to hide the engagement ring in a slice of Billy Miner pie.”

Owing to its prime location a half-block away from the Fort Garry Hotel, the Garry Street Keg has welcomed its share of famous faces, Stephen adds. In addition to A-list actors such as Robin Williams and Dennis Quaid and recording stars such as Burton Cummings, he can’t think of too many National Hockey League or Canadian Football League players they haven’t hosted at one time or another.

“Oh, and don’t forget (former Soviet Union leader Mikhail) Gorbachev,” Howard pipes in.

That’s right, Stephen agrees. In 2012, Gorbachev was in Winnipeg to take part in We Day festivities taking place at what was then called the MTS Centre. The Keg was one of the sponsors and during a post-event meet-and-greet, organizers introduced Gorbachev to Howard, instructing him that Howard’s resto served the “best steak in town.”

That settles it, the Nobel Peace Prize winner announced; that’s where he’d be chowing down that evening. (According to the Russian-speaking server assigned to Gorbachev’s party, he opted for French onion soup, mashed potatoes and a New York striploin prepared medium rare.)

Last fall, it was announced that construction of a mixed-use apartment tower at the intersection of St. Mary Avenue and Donald Street was recommencing, following a series of delays. The project is slated to include a new Keg Steakhouse + Bar at ground level. There hasn’t been an official announcement yet, but that development will almost certainly spell the end of the Garry Street outlet.

“For now, the plan is to continue to operate out of our Garry Street location right up to the time we move over in summer or fall of 2026,” Stephen says.

“So for sure, there’s still plenty of time to get in a few more nostalgic visits.”

david.sanderson@freepress.mb.ca