Why 20 Volunteers Traded a Snow Day for a School Day
The story of Winona, Minnesota’s trails begins like many others.
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In the early 90s, a passionate group of riders saw potential in the deer paths crisscrossing a local bluff with ample elevation. They scratched in lines, driven by the simple desire to build what they wanted to ride. Fast forward to May 7-8, 2025, and that same pioneering spirit filled the room as Mayor Scott Sherman recounted this history to 19 visitors, all gathered for the Spring IMBA Foundations workshop. His welcome message of building with vision and fostering relationships to champion trails-based outdoor recreation resonated deeply, setting the stage for two days of immersive learning.
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Winona: Fertile Ground for Trail Growth
“Winona’s charm, in some ways, is the grassroots approach they took to trail development,” said Marty Caivano, IMBA’s Community Engagement Manager, “It’s not contrived feeling. You come here and can feel that it's a natural part of the community.”
Winona, a town of 26,000, isn't just a scenic spot on the Mississippi; it's rapidly becoming an emerging model trail community, making it the perfect host for a workshop designed to empower trail advocates. Those early, hard-won relationships proved invaluable when the city made its first significant investments in professionally built trails, welcoming IMBA Trail Solutions to help scope Bluffside Park in 2019.
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The local group, Winona Area Mountain Bikers (WAMB), exemplified scrappy determination, relentlessly pursuing their vision. Like many communities, they identified a critical gap: beginner-friendly trails. Addressing this head-on, late 2023 saw the debut of a new 2-mile green loop, a green bidirectional trail, and two intermediate gravity lines, created by IMBA Trail Solutions and Rock Solid Trails. This strategic "two-pronged approach"—creating accessible entry-level riding alongside mountain bike optimized lines—was precisely what Winona needed to ignite further trail use and welcome a broader range of riders.
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The "cherry on top" was the addition of three skills-based zones near the main parking lot created by Pathfinder Trails. These zones are pivotal, offering a space for locals and regional visitors to safely build confidence and preview features they'll encounter on the expanding Bluffside system.
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Fertile Ground for IMBA Foundations
With Winona’s progress as the backdrop, the IMBA Foundations team guided participants through the intricacies of the trail development process. This workshop delves into crucial stages: visioning, community engagement, funding strategies, land access, assessment, meticulous planning, thoughtful design, quality construction, and sustainable stewardship. By dissecting case studies, sharing best practices, and drawing from personal success stories, the workshop laid a solid foundation tailored to the diverse needs of each participating community.
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At the core of these discussions lay the principle of true sustainability. As facilitator Mike Repyak of Kayperworks Consulting emphasized to participants, "Sustainability is more than just minimal impact to the ecosystem; it needs to be viewed through three different lenses: environmental, social and economic." This holistic view was palpable on day one as attendees walked the Bluffside Trail System alongside Ama Koenigshof, IMBA Trail Solutions Director of Planning & Design, experiencing the synergy between the newest trails, the engaging skills area, and the system's well-loved legacy trails.
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The Winona Model & Shared Experiences
This two-day experience extended beyond presentations; it was about learning in action and fostering connections. The field visit to Bluffside Park wasn't just a tour; it was a living case study. Participants saw firsthand the tangible results of Winona's dedication.
The power of witnessing such a journey wasn't lost on attendees. Emily Berry from Rapid City, South Dakota, vice president of Black Hills Bike Hub, reflected on the value of learning from Winona’s history. "Seeing their progression of having accessible land that had trails on it, but not bike-optimized trails and learning about some of the pitfalls that they hit along the way was motivating." As Sean Pantellere of the National Interscholastic Cycling Association (NICA) observed about Winona's collaborative success, "It sounded to me like it was a group that really understood what everybody else's role was going to be and nobody was overstepping their bounds, because they had mutual respect". This spirit of mutual respect and collaboration was a key theme throughout the workshop and transparent sharing of a host community's process was invaluable.
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Moreover, the workshop fostered a powerful sense of camaraderie. Evan Walterman, Trails Director for Black Hills Bike Hub, noted, "It's refreshing to talk to people that are trying to do the same thing you are." This networking aspect, connecting with like-minded individuals facing similar challenges and opportunities, is a cornerstone of the Foundations experience.
The Ripple Effect: 3 key takeaways for your community
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Winona's journey, amplified at IMBA’s Foundations workshop, offers a potent blueprint for other communities aspiring to create or enhance their own trail systems. The event culminated in a robust open forum Q&A with the IMBA team and a community panel, crystallizing several key takeaways:
- Vision and persistence pay off. Mayor Sherman’s reflection, “We need beginner trail that can get us up and down and more people into the sport. And now, we have that. That…to me…is a dream come true,” underscores the power of holding onto a vision, especially one that enhances community access and enjoyment.
- Multi-faceted funding is crucial. Successful trail development often hinges on a multi-faceted funding approach. As Mayor Sherman advised, “You gotta have private investment, you gotta have local fundraising. You also need to get into the grant dollars: the federal, the state, etc."
- The "why" drives success. The impact of trails is far-reaching. Visit Winona’s Kate Carlson highlighted that, "In 2024, 33% of Winona visitors participated in outdoor recreation; that’s an all time high for our town." This is a testament to the draw of quality outdoor amenities and translates to tangible economic benefits, as echoed by WAMB’s president and Adventure Cycle & Ski shop employee, Zach McKinney, who noted, “I get to work on much higher-end bikes than ever before these days.”
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Winona, Minnesota, stands as a shining example of how a grassroots movement, fueled by passion and collaboration, can transform a community into a celebrated trail destination. The Spring 2025 IMBA Foundations workshop not only highlighted Winona's achievements but also equipped attendees with the knowledge, inspiration, and connections to cultivate similar success in their own backyards. The journey from deer paths to a model trail community is within reach for those ready to learn, collaborate, and build.
Want more of Winona's story? Watch this video:
