Bailey Bestul

Winona teen launches history tour business



Not every adult is comfortable getting a history lesson from a 16-year-old. Since he launched Pointour, his business offering walking tours of downtown Winona architecture and history, two weeks ago, Bailey Bestul has encountered some skeptics.

"I think there's a general wariness because people think, 'You're a minor. I don't know if I trust you.' So it's been kind of a battle for credibility," Bestul said.

Take a closer look, though, and Bestul seems well-suited to be an ambassador for Winona's historic district. While other 16-year-old boys master the latest shoot 'em up video game, Bestul has spent hours researching the minutia of downtown Winona history in the files of the Winona County History Center Archives. How much do the marble columns supporting Winona National Bank's regal facade weigh? Who designed both the Winona County Courthouse and the Basilica of Saint Stanislaus Kostka? Bestul knows. He has spent the past year perfecting a business plan for Pointour, with help from entrepreneurial mentors and lawyers, plotting out his cash flow needs and marketing strategy, even what he will do if the economy suffers another recession. Bestul is an architecture buff, too. For a long time, he has been a voracious reader of architecture blogs and magazines. He is brimming with energy and enthusiasm, too, and comfortable in front of a crowd. Bestul is a theater lover who performed in "The Merry Wives of Windsor" in last year's Great River Shakespeare Festival (GRSF), is acting in this year's "Much Ado About Nothing," and has acted in productions at Rushford-Peterson High School and Winona Senior High School.

"I just think of myself as an adult," Bestul said when asked about being a young entrepreneur. "I don't think of myself as the 16-year-old going to set up a business deal. I'd probably run out of the room if I did."

Bestul and his family moved to Winona last year from Fremont, an unincorporated hamlet amid the corn and bean fields south of Lewiston. When Bestul came to the island city, the architecture made his head buzz. In addition to Victorian, Italianate, St. Anne, and Romanesque style homes and offices, Winona is full of buildings designed by Prairie School architects, an architectural movement that includes the famous Frank Lloyd Wright. The roofline of Winona buildings were especially fascinating for Bestul. They are full of ornate details that are easily missed from a distance and many of their original owners printed their names in stone or brick along the building's top, creating a sort of "who's who" list of early Winona, Bestul said.

The buildings of Winona have so many amazing stories that many Winonans do not know, Bestul continued. His eyes got big as he talked about Merchant's National Bank. "Some architecture critics consider it one of the most important contributions to 20th-century architecture anywhere," he said. "So we have really influential buildings all around us." With such fantastic architecture downtown and a history full of pioneers, lumber barons, prostitutes, bootleggers, and immigrants, Bestul was amazed that Winona did not have a guided walking tour to share that history with visitors and residents. So he started one.

Bestul gave his first tour on Wednesday, July 15, and has given a few more since, mostly to tourists in town for other events. "Everyone I've talked to said, 'That's great,' or, 'I've been thinking about doing something like this.' Well, there you go, I did it for you," he said, laughing.

Bestul's tours are full of hidden treasures, in part because several organizations have allowed him to lead trips inside their facilities. He shows visitors the 15-ton vault that once held Merchant's National Bank's most precious deposits, and the pipes inside the Winona Waterworks that are decked out in brass and black walnut, in part because of the first waterworks director's unusual penchant for finery. "It was a back room that no one would see into but him, but he put thousands and thousands of dollars into it because he wanted to have a luxurious setting — just for him, I guess," Bestul said. As he strolled past Legends Tavern, Bestul recalls the building's former use as a brothel. He pointed out gargoyles set in the grass of the courthouse lawn, and shared the story of one hidden treasure tour-goers will never see: a time capsule the Watkins family buried underneath the column of the Winona National Bank entrance when it was built in 1916.


"He's still in high school," marveled Visit Winona Director Pat Mutter. "Here is someone who is really making use of his time in the summer to be a part of the community and showcasing downtown and its architecture. He is really getting to know a lot of people along the way and just spreading his excitement about Winona."

Mutter helped Bestul develop his plans for the tours, suggesting that he test out the length of the walking tour with people of different age groups and that he make time for water breaks and places to rest. She continued, "To have the perspective of someone his age starting something like this from scratch and doing all the research and finding really interesting factoids about the buildings has been just wonderful for us to appreciate."

Bestul said he hopes to grow the business this year, his junior year. Beyond that, his plans are less definite: "I'd like to continue business, but I also love theater."

More information about Pointour is available at by visiting the Pointour tour company Facebook page.


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