BY JOE ARCE AND COREY CRABLE
In depth report,
This is the second and final part of a two-part series
Rupert Aguirre has known life as a hobo, but he never fancied himself a storyteller. Now, with an autobiographical manuscript written and new friends made at the 2025 National Hobo Convention (Hobo Days) in Britt, Iowa, Aguirre has become masterful at helping bring others into his world.
Since he began becoming involved with hobo advocacy in the Westside neighborhood in 1979, Aguirre has shared his story of living as a hobo in the 1960s, weaving tales designed to inspire others to believe in the resiliency of the human spirit – and to raise awareness of the hobo community as a group of people living as a subculture with its own standards and its own values.
And though Aguirre says he had retired from speaking at events last year after nearly 50 years, he just couldn’t resist the allure of having the opportunity to speak at the National Hobo Convention, which has taken place annually in Iowa since the dawn of the 20th century. From the moment he arrived, Aguirre says he was amazed by the sea of humanity, of people from such varied backgrounds and countries.
“It’s not only just a convention. They have music. They have parades. They have everything. Altogether, I would probably say hundreds of people were there,” Aguirre says. “…It’s like a mecca. They were from everywhere, even European countries. It’s as if they’re magnetized to go there.”
Aguirre’s presence at the convention was thanks to Beth Gretillat, with Britt’s Hobo Day Association, which organized the event. She says the event is a place to come and share pride in the hobo community. Shame, she says, has no place there.
“For us and Britt and our committee, they’ve been here since 1900, so we’re very proud of having them come back,” Gretillat says. “Most of us know many couples and their stories. They’re such a strong group of people. They’re very resilient, they have unique stories and backgrounds, and we love getting to know them.”
Speaking of couples, the national convention’s most famous couple are the king and queen, crowned at each event. Selected by the audience following self-introductions, the convention’s king and queen are tasked with doing their best to spread awareness of the hobo lifestyle until the next convention, throughout whatever community in which they might find themselves.
Gretillat says that some convention attendees find success following their stint riding on the rails, but that the pull to travel and explore remains potent.
“We did have a past king, and his name was Adman, and he became an advertising executive after he rode trains in his youth,” she says. “He lived in Wazeta, Minnesota, and he started this advertising company, but every year for a couple months he would still hop trains. He had that wanderlust, which most of those people have, that he just needed to go hop trains and explore and do his thing. … It was something that helped them become the people they are today.”
Aguirre says he was immediately welcomed by those in attendance at the convention and even encouraged to try to win the top spot as king.
“As soon as I saw (Gretillat), she introduced me to so many people. She gave me an honorary patch,” he says. “She’s also said that I was one of the most qualified to try to be the Hobo King, which is the highest honor that there is. And you have to remember there’s a lot of people from all over the country trying for that.”
Even though Aguirre says he lived as a hobo for a little more than five years, he met others at the convention who have lived the lifestyle for decades.
“There’s hobos now who have been doing it for 30, 40, 50, 60 years. And that’s their lifestyle still,” Aguirre says. “But I made a lot of friends there. … Each one has a unique story, and they share their stories, and this is what’s so beautiful there, that you could learn from everyone else.”
Aguirre’s son Chris says he plans to attend the next convention and cheer on his dad as he tries to claim the coveted Hobo King title.
“I’m actually going with my dad next year. They’re going to have another convention coming up in August next year. So I’m going to go with him there as well. He’s going to try to run for Hobo King, and I’m going to help him as much as I can,” Chris says. “We’ll go there and visit it and just enjoy the festivities. It’s really neat to meet people in that lifestyle, but they’re just everyday people.”
Chris adds that he feels that pride for his father, who has learned about life and made friends along the way in his journey as a hobo.
“I’m very proud that he’s expressing himself and sharing what he did and what he learned,” Chris says. “He’s met so many people along the way, and he’s still meeting people.”
Gretillat says Chris and others are welcomed warmly at the convention, where stories are told and experiences shared.
“I see a lot of children or grandchildren coming because they were so proud of their family members and they want to come share that experience and learn more about their family. … I just hope they know that we love them coming back,” she says. “We have a lot of children of hobos that come every year just because they learned about their parents’ background, history, and they want to come back, connect with their parents’ history, learn more about the hobos, the lifestyle they chose, and they really enjoy sharing those stories with everybody. … We love them sharing stories. We love that they bring in new people.”
Aguirre says that the first time he attended the conference, he remembers thinking, “I’m home” – a feeling he hopes others in his situation have and can appreciate. It’s such a unique experience, and everyone just has respect for each other,” he says.
Aguirre says that at the next convention, he plans once again to visit Britt’s National Hobo Museum, where some of his writings are kept. The museum, housed inside a small vintage movie theater, also displays artifacts from the past century, many of them from the Great Depression, when an estimated 250,000 hobos traversed the nation in boxcars.
And though the number of hobos has decreased in America in recent years, in these uncertain economic times, those numbers very well could see a rise.
“One of the things that was said in the symposiums and the convention is that America better be ready for an influx of hobos because the way this economy is going, the way the government is going, there’s going to be a lot of homeless people,” Aguirre observes. “And where do they turn to if they can’t be helped? They’ll be helped in places like the homeless shelters, the hobo camps. There’s going to be a lot of people like that if it doesn’t change, and hopefully it does.”
Until he is able to tell his story to a crowd like the one in Britt every August, Aguirre says his 600-page manuscript will tell his tale. It’s one of the many ways that the hobo community is preserving its history, to show others that they not only exist and contribute to society, but that they also matter.
“It’s a rough life,” Aguirre says, “but thanks to God and Our Lady of Guadalupe, I survived.”
For more information on the convention and the museum, visit https://brittiowa.com/attractions/hobo-days/.
