Caldwell Fellows Wilderness Expedition Expands
A New Partnership with Outward Bound
The Caldwell Fellows Wilderness Expedition, for decades, has pushed students out of their comfort zones through a structured experience of challenge and support, with a proven impact on personal development. Countless alumni have cited their wilderness experience as a catapult experience in their formation, launching them into deeper self-awareness and inner strength, crucial attributes of servant leadership. The dedication of alumni and the vision of Jerry Barker have provided a wilderness opportunity for 8 to 10 Fellows each trip. This legacy has laid the foundation for a new chapter in the Caldwell wilderness program, expanding capacity to serve more students while addressing the growing complexities of trip planning and risk management through our self-run model.
Caldwell Fellows is embarking on an exciting new chapter—one that honors our history while positioning us for the future. We are thrilled to announce a new partnership with Outward Bound that will continue to include alumni in program leadership, guiding students in the reflection, values, and practices of Caldwell Fellows. Outward Bound is one of the nation’s leaders in outdoor education. Their mission, “To spark lifelong growth through challenge—outside,” is accomplished through “adventurous learning, rooted in the outdoors, to unlock confidence, curiosity, and the skills to thrive with purpose.” Outward Bound has 9 schools in the US, with locations in California, Colorado, Minnesota, North Carolina, Maryland, Pennsylvania, New York, and 2 in Maine. In our first two years, we will work with the Voyageur Outward Bound School to integrate our programming into an exciting research study they are conducting on character development education. Read on to learn more about this powerful new model of Caldwell wilderness education.
Honoring Our Legacy
The Caldwell Fellows Wilderness Expedition began in 1985 with an Outward Bound trip to Everglades National Park. Over four decades, our wilderness programming has ranged from the Everglades to the Cascades, from the Sierra Nevadas to Utah’s Canyon Country, and many places in between. It has been an act of courage, determination, and resilience that has transformed generations of Caldwell Fellows.
For nearly three decades, the expedition flourished under the extraordinary leadership of Jerry Barker, Mark Wagoner, and numerous dedicated Caldwell Fellows alumni who managed these transformative experiences. Though we tragically lost Mark, Class of 1994, to an airplane accident in Alaska in 2003, his passion for wilderness education lives on. The Wagoner Fund honors Mark’s life by supporting the development of future outdoor educators. This fund has enabled Fellows aspiring to join the ranks of alumni wilderness leaders to complete wilderness leadership certifications. Thanks to the faithful support of this fund by so many, this opportunity will long persist.
As the demands of risk and safety management in higher education have evolved, we recognized the need to adapt our approach while preserving the essence of what makes the Caldwell Wilderness Expedition so transformative. This past summer, we were fortunate to have the guidance and expertise of recent Wilderness Expedition alumni leadership members who helped us evaluate potential partnership options. We extend our deepest gratitude to Rob Horner, Jenna Pye, Thomas Harris, Julia O’Brien, Val Ryba, and Pablo Campos for their thoughtful input and dedication in helping us ultimately decide to move forward with Outward Bound. Their commitment to maintaining the integrity and impact of the Wilderness Expedition while ensuring its sustainability for future Fellows has been invaluable.
Celebrating Our New Partnership
In this new partnership, Outward Bound’s expert staff will now manage the logistics, risk management, and outfitting for our expeditions, allowing us to provide the safest and most impactful experiences possible. In collaboration with Chester, who holds a master’s degree in outdoor education, and Val Ryba, Class of 2024, Outward Bound is developing an experiential leadership development curriculum specifically aligned with the spirit and mission of the Caldwell Fellows community. This curriculum will honor the developmental traditions established by our alumni leaders while incorporating Outward Bound’s decades of expertise in wilderness education.
This year’s expedition will take place August 7-14, 2026, and will feature canoeing in the pristine Boundary Waters Canoe Area Wilderness. We have spaces for 18 intrepid students to participate in this unforgettable journey of self-discovery and leadership development.
As part of our partnership with Outward Bound, we are also joining a multi-year character development research and assessment project led by Outward Bound, the Enrollment Management Association, and the National Association for College Admissions Counseling. This exciting collaboration will investigate the role of character in college success, contributing to broader conversations about holistic education and leadership development. Our participation in this research will help us better understand and articulate the transformative impact of wilderness experiences on leadership development.
The philosophy of Outward Bound founder Kurt Hahn resonates deeply with our mission. He believed education’s foremost task is “to ensure survival of these qualities: an enterprising curiosity; an undefeatable spirit, tenacity in pursuit, readiness for sensible self-denial, and above all, compassion.” This convergence of values—Outward Bound’s commitment to developing character, leadership, and service through challenging wilderness experiences and the Caldwell Fellows’ dedication to servant leadership—creates a robust foundation for the next era of our Wilderness Expedition. Both organizations believe that pushing beyond one’s comfort zone in the context of community builds empathy, resilience, and a deeper understanding of one’s responsibility to serve others. The wilderness becomes not just a classroom for technical skills, but a crucible for developing the moral clarity, courage, and collaborative spirit that define effective servant leaders.
The range of programs offered by Outward Bound, from backpacking to canoeing through the wilderness, will enable us to provide a rotation of wilderness options that accommodate Fellows’ differing physical abilities. It is our ambition that as we move forward, EVERY Caldwell Fellow will undertake the challenges and rewards of the Wilderness Expedition before they graduate.
Take a peek at a few photos from Jerry Barker’s extensive archive of trip photos below.
