This story originally ran as part of the American City Business Journal’s Business of Travel Series, sponsored by Visit Milwaukee.

It started on a plane in September 2021, flying from Milwaukee to Washington, D.C. In one seat was Peggy Williams-Smith, a Milwaukee native, lifelong hospitality professional and the first woman to lead Visit Milwaukee in its more than 50-year history. In the other was Cavalier Johnson, then president of the Milwaukee Common Council and not yet mayor. 

She had spent more than two decades with Marcus Hotels & Resorts, rising through the ranks before taking over the destination marketing organization in 2019. He was ascending in politics, about to become Milwaukee's first Black mayor elected to a full term. She carried the poise of someone who had sold a thousand banquets. He had the conviction of someone who had knocked on a thousand doors.
 

Somewhere over Ohio, the small talk gave way to real talk. They traded views on Milwaukee’s challenges, opportunities and image. By the time the wheels hit the tarmac, they had the beginnings of a working alliance that would help reshape the city’s national profile. 

That partnership later helped land the 2024 Republican National Convention, a four-day spectacle that brought 50,000 visitors, 15,000 credentialed journalists and an estimated $321.5 million in total economic impact. 

“To me, it was never about politics,” Johnson said. “It was about business. It was about elevating the city and showcasing Milwaukee, elevating the city’s profile across the country.” 

He credits Williams-Smith’s tenacity. “There is nobody better to work with than Peggy,” he said. “She gets it. She understands not just what her role is, but what my goals are as mayor in terms of growing the city.  And she sees how tourism and hospitality weave into that.” 
 

Rewriting the Story 

Williams-Smith knows Milwaukee’s stereotypes. She has heard them all her life. But she also knows the version of the city she has lived and worked in for decades: the one with a skyline framed by Lake Michigan’s endless blue, a summer calendar that leaves no weekend without a festival, a dining scene owned almost entirely by locals, and a performing arts community that can hold its own against any city twice the size. 

“When I took this job, I said I would do every media interview requested, but I was going to focus on the good,” she said. “That is what someone in my position should do.” 

The good, in her telling, is abundant. It is Baird Center’s $456 million expansion. It is the city’s miles of public lakefront. It is the restaurant list that could keep a convention-goer eating well for weeks without touching a chain. 

Take the Adepticon convention. The 10,000-person miniature wargaming event took over the expanded Baird Center in late 2024. When they weren’t meeting, they were eating. 
 

“In Milwaukee, it’s just easy,” said Shelley Sparks, exhibitor and sponsor coordinator. “Just walk out the front door and you have numerous great options for dining at your fingertips.” She rattled off the list from memory: Mader’s, Calderone Club, The Capital Grille, 3rd Street Market Hall and Safe House, all locally owned and operated. 

Williams-Smith points out that Milwaukee’s dining options got a tidal wave of rebranding juice when Bravo’s “Top Chef,” an award-winning foodie reality show with an international audience, accepted Visit Milwaukee’s offer to stage its 21st season in the state with its home base in Milwaukee. 

“‘Top Chef’ changed the entire narrative around food,” she said. “People have seen what Milwaukee has to offer from a culinary perspective. People base travel decisions on experiences, and food is one of those things.”
 

From Crisis to Confidence 

When Williams-Smith stepped into her role in late 2019, Milwaukee had just been chosen to host the 2020 Democratic National Convention, a coup for a mid-sized city. Months later, COVID-19 hit, and the convention, along with the city’s tourism economy, evaporated almost overnight. 

Her response was to double down. She became the Milwaukee hospitality industry’s chief advocate at the state and local level, keeping communication lines open, pushing for relief and arguing that an expanded convention center was vital for Milwaukee’s future. “I knew conferences would come back,” she said.  

“They change people’s lives. We needed to be ready.” 

By August 2022, the gamble paid off: Milwaukee was awarded the 2024 RNC, to be hosted in the newly expanded Baird Center, making Milwaukee the first city in decades to host back-to-back political conventions. 

Then, on the eve of the RNC, the unthinkable happened. There was an assassination attempt on the Republican nominee. “It had me in tears,” she said, “because I thought I was going to be the first destination to cancel two conventions back-to-back.” 

Trump survived, and the convention went on smoothly. Williams-Smith would end each night in her hotel room, watching national news feeds show off her city’s venues, restaurants, skyline, and lakefront. “It was absolutely mind-blowing,” she said. “They were talking about how great and welcoming and warm Milwaukee is. That was incredible to me.” 
 

The Bigger Picture 

Her work is not just about filling hotel rooms. It is about reframing how Milwaukee is seen by visitors, by the national media and by Milwaukeeans themselves. She has built campaigns that lean on partnerships, community pride and a team she has molded to be nimble and quick to adapt. She mentors women in business and actively supports charitable causes, including the United Way of Greater Milwaukee & Waukesha County, the United Performing Arts Fund and the American Red Cross. 

The results speak for themselves. Under her leadership, Visit Milwaukee has helped land marquee events, spotlighted local businesses on national platforms and brought new energy to the city’s convention and hospitality sectors, all in just under six years. 

“It is about creating a cycle,” Williams-Smith said. “Visitors come here for a conference or an event. They fall in love with the city. They come back with their family. They invest here. They move their business here. That is economic development, and tourism is the front door.” 

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