OSKALOOSA — When Iowa Economic Development Authority (IEDA) and Iowa Finance Authority Director Debi Durham walks through downtown Oskaloosa, she doesn’t speak like a visitor. She talks as someone who has been watching the community’s steady rise for years, someone who sees the long arc of transformation. After touring the district again Thursday afternoon, Durham said she left with the same feeling she has every time she stops in Oskaloosa: inspired.
A Downtown Built on Collaboration
Standing on the square after her tour, Durham reflected on what sets Oskaloosa apart. She pointed to something that isn’t visible in a façade or tied to a single project. It’s the mindset.
“Every time I come back, I leave inspired,” Durham said. “You really do have city government, the school district, volunteers, nonprofits, and businesses all working together toward the same goal. You don’t find that everywhere.”
The cooperative energy she describes isn’t just a tagline. It has become the backbone of Oskaloosa’s revitalization work. From historic preservation to community festivals to youth engagement efforts, multiple organizations have aligned their priorities and pooled their influence. The result is a district that not only looks different than it did a decade ago but operates differently too.
Linda Howard, chair of the Oskaloosa Main Street Design Committee, has seen this shift firsthand. She said most communities are lucky if one of the “three legs” of downtown revitalization (nonprofits, private business, and government) functions consistently. Oskaloosa, she said, has all three working in sync.
“I never encountered a place where all of them were functioning and helping together,” Howard said. “It’s truly amazing.”
Investment That Brings More Investment
During her afternoon tour, Durham stopped at Spirit Cafe, Hunter’s Gift and Coffee Cafe’s lower-level retail space and potential upper-story housing project, the construction site of the new Jaarsma Bakery, the Book Vault, and Brown’s Shoe Fit, seeing firsthand how local investment continues to build momentum. Durham’s visit included a stop inside several completed and in-progress Main Street Iowa Challenge Grant projects. Oskaloosa has a long track record of success with these grants, earning an unusually high number of awards for a community of our size. This trend continued this fall, when another Oskaloosa project was selected among statewide winners.
“Whenever Oskaloosa applies, you bring us a winning application,” Durham said. “You have a legacy of over-delivering. When we invest in you, we know we’re going to see a strong return for Iowa taxpayers.”
The numbers support her claim. During the city’s multi-phase downtown façade improvement effort from 2016 to 2023, buildings that participated in the program saw property values rise an average of 41 percent. The increase for non-participating properties citywide was 11 percent.
“We saw how investment brought more investment,” said Shawn Christ, Development Services Director for the City of Oskaloosa.
That momentum led city leaders to take a bold step. When participation fell short for a potential fourth phase of state-funded façade work, the city chose to launch its own matching-grant program. The Community Oriented Revitalization and Enhancement (CORE) Fund budgets $50,000 per year for exterior improvements, architectural design support, and structural upgrades.
“It’s risky, but we believed keeping the momentum going mattered,” Christ said. “If someone needs help with a roof, a side wall, the back of a building, or even a service line needed for fire suppression, the program can support it.”
Durham applauded the decision.
“None of us can do this alone,” she said. “Great partnerships are what make everything work.”
A Portfolio of Local Champions
Howard believes one reason Oskaloosa has stayed ahead of the curve is its range of engaged, homegrown stakeholders.
With our solid manufacturing base here, local companies are important to Oskaloosa’s success. “Our businesses have been instrumental,” Howard said. “They’ve invested in buildings and workforce, supported our retail and restaurants, and volunteer and give back to our community.”
Grassroots entrepreneurs play a role, too. Howard pointed to business owners who invest in community spaces, support festivals, and donate time and supplies without seeking recognition. Even seemingly small decisions, like Mahaska Drug buying an ice cream truck for local events, reinforces the culture of community participation.
And then there are the philanthropic groups. Oskaloosa operates with a level of foundation support rarely found in communities of its size. In the past year alone, the Mahaska County Community Foundation distributed $120,000 in local grants. The Golden Goose Club, a women’s philanthropic group, gave over $80,000 to projects ranging from murals to alley enhancements to public event infrastructure. The George Daily Family Foundation remains a transformative force, recently supporting a major YMCA expansion and projects throughout the entire community.
“You have three very proactive foundations,” Howard said. “It’s a tremendous advantage.”
A Downtown That Keeps Adding Layers
One of the clearest signs of Oskaloosa’s evolution, both Howard and Durham said, is how residents continue investing in new ideas instead of settling for what already works.
The district’s alley revitalization projects, public art installations, and community festivals illustrate that mindset. Local arts organization FACE helped create murals and sculpture walk pieces that have become recognizable landmarks. Puppetists and performers appear in parades and festivals. Volunteer groups animate streets and alleys year-round.
And now, new concepts are rising.
A children’s museum is in development. A youth innovation hub has begun taking shape inside a downtown building. Restaurants continue to open. Creative retail experiences are emerging. Side streets and residential corridors have become the next frontier for targeted investment.
Durham said this layering effect is what gives Oskaloosa long-term staying power.
“You’re not just improving the square,” she said. “You’re strengthening the blocks around it, the neighborhoods, the housing. Investment keeps expanding.”
She noted that the strongest Iowa downtowns five years from now will be the ones pushing themselves today. Her advice to Oskaloosa: keep going.
Oskaloosa Main Street as a Model for Other Communities
While Oskaloosa benefits from state partnerships through IEDA and Main Street Iowa, Durham said the relationship works both ways. She sees the community as a mentor for other towns starting their own revitalization efforts.
“For many communities just beginning the Main Street journey, it’s important for them to come here and say, ‘This is what we can be,’” she said. “You didn’t start at this point. You took it one step at a time.”
That story matters, she said, because new Main Street programs sometimes feel overwhelmed by the scope of work ahead. Oskaloosa offers a living example that progress is possible, measurable, and replicable.
“Once you’re in the Main Street family, you’re always in the family,” Durham said. “And Oskaloosa is a very valued member.”
Local Flavor and Lasting Impressions
Durham’s tour also included a visit to Spirit Cafe, the student-run eatery operated by Oskaloosa Schools. She said both the mission and the meal stood out.
“The food was amazing, but watching those students shine, that is the heartwarming part,” she said. “They are so proud of what they’re doing.”
Before leaving town, Durham checked off a personal tradition: stopping by the Book Vault and picking up her annual supply of holiday paper napkins from Hunter’s. She laughed as she admitted it has become one of her favorite seasonal rituals.
“I don’t order them online. I come here every year,” she said. “Even if I’m not in the area, we make a stop in Oskaloosa before Christmas.”
It’s a small detail, but one that reinforces what many locals already know. Oskaloosa has become a place where people want to linger.
A Community Poised for What Comes Next
As the tour wrapped up, Durham paused to reflect on the future. For her, the most encouraging sign isn’t a single project. It’s the community’s shared sense of purpose and collaboration.
“You’ve got a lot of great things going on here,” she said. “Keep dreaming big.”
In the end, Oskaloosa’s story is not just about revitalizing buildings. It’s about building confidence. A community that once hoped for revitalization has learned how to create it. That transformation, Durham said, is what makes Oskaloosa stand out statewide.
“When I saw this on my schedule, it made my day,” she said.
