At a point in time, Osborne and River was like a small town. On the southwest corner once stood a drug store and across the street stood a bank. Osborne was a commercial street in a residential neighbourhood. However, by the 1970s some of the more sprawling estates around river gave way to apartment buildings. Along Wellington Crescent, not too distant from the corner, apartment after apartment went up along the Assiniboine River. And along Roslyn even more apartments went up.


The tallest apartment of them all in western Canada for a number of years was 55 Nassau built in 1970. While none was as tall in years after, there were several built in surrounding area all over 20 floors.

The increasing density brought foot traffic to the Village. But affordability didn’t come from high rises, it came from single family homes being turned into multi-unit housing that was far cheaper than places like posh 55 Nassau. Stately family homes became several apartments in the 1970s and through the 1980s. Not condos but small apartments.

In the last several years some of the older multi-units houses have been being torn down for posher condo and apartments. The economic diversity is not nearly what it used to be in the Village, but the density has increased. The rent overall in the city has increased leading to affordability issues. This has translated into increasing commercial rent on Osborne properly.

In New York, they call it luxury blight where a commercial street that once hosted banks, barbers, greasy spoons along with hardware stores now has dress shops that attract suburbanites for a frock that might be a month’s rent for someone. Winnipeg never had the same sort of really posh shops but it did have a few more exclusive retailers in the area.

Some started earlier enough in the less expensive days to actually buy their property. Those places turned out to last the longest. However, as owner operators turned to straight landlords, the renters paid rent but were not able to have equity in the land.


Restaurants can come and go, but they are at least able to offer something that Amazon can’t easily disrupt. However, a start up is not going to be interested in a 10 year lease unless it has corporate backing. And so you see a lot for lease signs. And in some case whole buildings that go unused year after year. For what? For the perfect tenant. It seems no consideration is given that empty storefronts or buildings can perpetuate more blight.

In Osborne Village there are spots that have sat empty for years. Some spaces such as the Osborne Village Hotel have been demolished and sit empty with no construction start in sight. Presumably, if they could have gotten away with it, they might have made made it paid parking. That is an old landlord game. Promise to develop and then have a parking lot for decades.

Osborne Village has been resilient although cyclical in major part due to a grocery store and pharmacy that are all within walking distance for thousands who live nearby. Throw in some convenience stores, some fast food joints, a post office and liquor store and a resident could walk in minutes to and from home. Not even a need for a bike with that type of proximity.

The River Avenue to Confusion Corner part of the street is the commercial part of the Village and in recent years, the most unstable. As mentioned, the high price of commercial rent and the long leases requested by landlords is a disincentive to start-up shops and restaurants. The size of some of the spaces is also tough. If a restaurant’s business model depends on a lot of parking then Osborne is not the right place.

What surprises a lot of people about Osborne Village is the scale. Even after decades, it is still no higher than three floors most of the way down. A large amount are one floor buildings. There has been an attempts to go higher at the Gas Station Theatre but it has failed to gain traction. Closer to Fort Rouge station, a taller office building has gone up and beside it is a stalled residential tower.

There has been a cry for more parking but it is unclear how maybe 300 spots on a place, say like… the Osborne Village site would work. You would have to have security, a time limit and if it was privately owned…a price to pay. No doubt if the city allowed this, buildings would be knocked down here and there to offer parking. But how would it help the commercial area? Large gaps would be windswept and still a fair walk to where you were going. It would be a series of strip malls where constant vigilance would be needed so that people only shopped in your store rather park and head elsewhere.

If the point is getting more foot traffic, the lack of places to reach on foot is an issue. It would like being in a mall with a store only open every few spots. The mall would not survive that way. A street is not a mall. A street survives with some parking but in Osborne Village, public transit and walking is more important than limited car spaces right in front of the shop. A company like Creative Audio, former long time Osborne Village resident, only had two spots out back that they had to constantly police. Someone buying thousands dollars of audio couldn’t even guarantee they could load their purchase anywhere near the shop. They eventually found a home on Provencher which is a lovely high streets that I’ve said good things about in the past.

With that in mind if River and Osborne is gateway proper to the majority of Village commercial activity, the businesses on that corner should be a big draw for people as early as possible in the day and as late as possible. It is why restaurants and coffee shops have proliferated over the years. If the business model of your company is lots of cars parked nearby 9 to 5 then Osborne is not a good match for you. For many, success has come from operating outside normal hours

Since 1975, Papa George’s was that place. The sign even said open till 4AM. It lasted till 2012 with a retirement of the owner. In principle, the late hours meant that people finishing late shifts, night owls and those coming from bars, movies and hockey games had a place to go to. And parking was easy to come by after 11PM. Several businesses had this idea including the Osborne Village Inn. And various shops and services blended into that model, some opting for the earlier opening to take in breakfast and coffee models.

Cornerstone replaced Papa George’s in 2014 after renovations were complete. Were it not for the COVID-19 pandemic, Cornerstone’s grub pub fare might still be holding sway on that corner. Indeed, there was a feeling that Osborne Village was poised to for a new uptick with all the approvals for new housing that had gone through. In fact, many housing units went up even as the pandemic locked things down. But restaurants such as Segovia and Cornerstone could not very well capitalize on restrictions as their customers dried up. No one was on the streets.

But there has been a few indications of what is to come even as we battle yet another wave of restrictions with the Omicron variant of COVID-19. Cannabis retailing ramped up in the pandemic. Osborne Village saw an early wave of openings. While they don’t have much street presence because of rules that make them frost their glass, they draw foot traffic and pay rent which should be sustained for some time. But cannabis shops don’t make for a neighbourhood or streetlife.

Stores, restaurants, bars have created vitality on the Osborne strip. The loss of the Osborne Village is beyond awful for what was lost. The nightlife, streetlife, vendor, restaurant is just a hole in the ground. It is unlikely that anything replacing it will be as important as that hotel was. Everyone awaits what will go up and when.


Still, when pandemic restrictions end, the corner of River and Osborne will see the closed Cornerstone restaurant turned into a Leopold’s Tavern. At the moment Leopold’s, along with other restaurants, are badly wounded with staff out sick with the virus. It is in interesting to note though how Leopold’s has been opening and operating locations in various parts of the city and succeeding. The opening of a location right at the entrance to the commercial area of the street is a real shot in the arm.

Leopold’s, a Regina-based group of restaurants, has tapped into the faux dive bar motif. The evolution of the bar/restaurant has evolved over the years. The lounge, beverage room and cabaret doesn’t always fit with a desire for people to stay in their neighbourhood in a place more scaled to the “everyone knows your name” size. The proof has been in the pudding because Leopolds’s has expanded to places others overlooked such as South Osborne, Academy Road and Bridgwater.

There is every indication that Leopold’s Tavern at River and Osborne will be entirely successful and a real draw for people in the area as well as visitors. And perhaps in 2022, the revitalization of the commercial strip of Osborne Village will begin a new iteration.

This has been a guest editorial by John Dobbin.
To read more from John, visit his blog Observations, Reservations, Conversations