The Uptown you're currently holding in your hands or reading online is our 500th issue. For a free, alternative street paper, just making it this far is an accomplishment worthy of celebration.

Indeed, Winnipeg's weekly source for arts, entertainment and news has gone through a lot of changes since it debuted in June 1987 as the Uptown Gazette, a bi-weekly business and lifestyle paper serving the downtown area.

It was a focus that made a lot of sense at the time: Portage Place Shopping Centre was set to open that fall, city council had just approved plans to extend the downtown skywalk system and the streets were buzzing with news of a potential new development at the CN's East Yard site - an area colloquially known as "the Forks." (In fact, Uptown's first cover featured a photo of the vacant land and a story that explored several proposed options for the site, which included a domed stadium, a new arena and a water park, as well as a year-round food market and a bridge with a restaurant on it...)

Brad Hughes, Uptown's co-founder, remembers those days fondly. His publishing company, Fanfare Magazine Group, was only three years old back then, operating from a James Street office just blocks away from its current Market Avenue location. Meanwhile, his old high-school buddy and soon-to-be business partner, Bruce Johnson, was doing a roaring trade at the Rorie Street Marble Club, a high-end nightclub located in the building that now houses Alive in the District.

"It just felt like a very exciting time in Winnipeg, specifically in the Exchange District," Hughes says. "We were really trying to mirror all that stuff that was going on."

The original vision for the paper was to report on the blossoming downtown art, nightlife and business scenes, but that changed when Hughes and Johnson realized they needed a broader audience to stay financially viable.

"It was a struggle," Hughes admits. "It only ever broke even when it was under my direction, because all the things we did cost money."

Uptown adapted to its fiscal realities by dropping its business section (as well as the "Gazette" part of its name) and re-branding itself as an arts and entertainment paper. Soon, it was being distributed city-wide.

Along the way, Johnson became more of a silent partner, abdicating many of the day-to-day decisions to Hughes, who functioned as the fledgling paper's de facto publisher. Quality was important, he says, and the small team worked hard to produce a product that was smart, relevant, well-edited, and meticulously proofed.

"I've always been really hands-on. Every word that's written in anything that we do, currently or at the time, I vet. I feel pretty confident that we didn't have a lot of typos in our publication, compared to a lot of similar, small street papers."

Not that there weren't detractors, of course. Over the years, Uptown was accused of being too fluffy, too corporate, and too positive. Still, Hughes says the five years he spent at its helm - he and Johnson sold Uptown in 1992 - were always exciting, if somewhat exhausting.

Five hundred issues in, Hughes says Uptown has developed its own distinctive voice and established itself as a definitive Winnipeg tastemaker.
"I love it when (other media outlets) say, 'Uptown says this is a great show,' or 'Uptown says this is a great disc,'" he says. "It has credibility - and that was a challenge, to get credibility."

Reflecting back, Hughes is clearly proud of the legacy he helped create.

"It's still coming out every week!" he says, marvelling. "It's still coming out and being this really exciting, influential thing.

"Now it's what I wanted it to be."

Uptown: A Timeline

1987 - Uptown is born! Published by Fanfare Magazine Group under the direction of Brad Hughes and Bruce Johnson, it runs as a bi-weekly downtown business and lifestyle paper.

1992 - Uptown is sold to Canadian Publishers, a change in ownership that kicks off a series of office moves - first from James Avenue to St. James Street (where it remains until 1994), then on to Main Street until February, 1997, when it moves back to St. James Street.

1997 - Uptown is sold to Platinum Publishing in November, and new owner Jason Nichol moves the paper into an office on Albert Street - a location that would become its home for almost a decade.

1998 - In June, Uptown is sold once again - this time, to Rosebud Publications, owned and run by Chuck Biggs.

2005 - Biggs sells Uptown to Canstar Community News Limited, a subsidiary of FP Canadian Newspapers Limited Partnership, the umbrella company that owns the Winnipeg Free Press, among other publications. Uptown moves out of the Exchange once again, landing back on St. James Street.

2008 - In February, Canstar's publications - including Uptown - are amalgamated into the Winnipeg Free Press and are now part of the paper's Community News Department. Uptown moves into its new Mountain Avenue home this spring.