Before joining DALC, Riley spent five years with the Ice Age Trail Alliance, the nonprofit partner of the Ice Age National Scenic Trail. During that time, she gained hands-on experience building and maintaining trails while learning from experienced trail professionals. She brings valuable expertise in sustainable trail design and construction, along with a strong belief that trails can create meaningful connections between people and the natural world.

In her role at DALC, Riley will help guide the growth of the Driftless Trail by planning, designing, and overseeing trail development from route scouting and mapping to construction and installation of trail infrastructure. She will also lead long-term trail care practices that keep trails safe, enjoyable, and compatible with the surrounding habitats and conservation goals. A key part of her work will be building relationships with volunteers and trail crews, helping people gain new skills while creating memorable experiences outdoors.

Riley especially enjoys working alongside volunteers and seeing people gain confidence as they learn new trail-building skills. She believes that time spent outside has the power to inspire stewardship and strengthen connections within a community.

When she is not working on trails, Riley loves exploring Wisconsin’s quiet and wild places in every season. Whether hiking, biking, paddling, climbing, or searching for wild foods to bring home in a handmade bag, she is always looking for ways to experience and appreciate the landscapes around her. 

We are thrilled to have Riley join the DALC team and help expand the Driftless Trail while creating opportunities for people to explore, connect, and care for this incredible region.

Originally from Rochester, New York, Kyle attended the University of Wisconsin-Madison, where she earned her Bachelor of Arts in English Literature. Over the past twenty years, her work has taken her across the country and through a wide range of roles focused on connecting people with places and experiences.

Her career has included serving as an instructor for the Brooklyn Center for the Urban Environment, educational outreach and tour work with Taliesin Preservation, and volunteering at the Chicago Architecture Center. She also spent many years in the restaurant industry, working her way into event planning while living in Chicago. In 2018, she returned to the Driftless Area to lead Taliesin Preservation’s events program. 

During the COVID-19 pandemic, Kyle recognized a need for stronger support of Wisconsin’s local food economy and founded Wander Provision, a Wisconsin-focused sandwich deli and specialty grocery celebrating small-scale farmers and producers. After five successful years building a community around local food, Kyle made the difficult decision to close Wander Provisions in March 2026. Around the same time, DALC was searching for an Events Coordinator. Given Kyle’s extensive experience in creating meaningful experiences and bringing people together, the timing felt like a natural fit and an exciting new chapter. 

At DALC, Kyle will help bring people together through events and programs at the newly acquired Wintergreen property. Her experience creating welcoming spaces and meaningful experiences will help shape opportunities for people to connect with the land, learn about conservation, and build community. As Wintergreen continues to evolve, Kyle’s creativity, hospitality, and deep appreciation for the Driftless will help make it a place where people can gather, explore, and experience the land. Her experience leading events and managing a business also brings valuable insight as DALC explores ways to grow programming at Wintergreen that is both sustainable and mission-driven. Through her work, Wintergreen will continue to grow as a welcoming destination where people can connect with the land, the Driftless Area, and one another.

Kyle lives in Spring Green with her husband, two dogs, seven chickens, and a duck. Outside of work, she enjoys swimming, reading, thrifting, and cooking. She also serves on the board of Savor the River Valley and chairs its newly formed Community Outreach Committee, reflecting her ongoing commitment to fostering community connections throughout the Driftless Area.

We are so happy to have you as part of the DALC team!