The next chapter starts outside.
Trailhead is four pieces that hold each other up. An annual wilderness expedition does the deep work: several days somewhere remote enough that titles don’t survive the drive, built around morning circles that ask one hard question each. Peer forums of eight to ten people carry that work forward, meeting on a steady rhythm for structured, confidential conversation. Between forums, the community gathers for learning sessions we call Waypoints, each built on thinkers like Richard Rohr, James Hollis, Parker Palmer, and Brené Brown, and each ending in conversation rather than a lecture. And every camper is paired with an accountability partner, the smallest unit of Trailhead and often the one that matters most.
No one is paid to run any of it. Costs are shared at cost. What is said in the circle stays in the circle.
The Northwoods Wilderness Retreat
August 2026 · Camp Highlands, Sayner, Wisconsin · Completed
Our first expedition grew straight out of the EO community. Seventeen campers, current members, alumni, and friends of EO St. Louis, men and women, drove north to a boys’ summer camp on Plum Lake that has been running since 1904. The campers had gone home for the season. For five days we lived in cabins with uneven wood floors, ate every meal at one long table, paddled, portaged, swam, and gathered each morning in a circle around one question. What am I becoming? What have I been carrying? What am I choosing not to see?
What we learned shaped everything Trailhead now does. The wilderness is the mechanism, not the backdrop: guards dropped in forty-eight hours that wouldn’t have dropped in forty-eight weeks of conference rooms. Peer forums formed on that trip and still meet. A keepsake of what campers chose to share, The Second Sunrise, lives with the group and will never be published. The full story is in the journal: The Second Sunrise, and the thinking behind the trip is in In Defense of Discomfort.
Trailhead Youth Crew
Launching January 2027
The same idea, pointed at a different transition. The Youth Crew is an outdoor leadership program for high school students, running January through June and culminating in a major camper trip in June 2027. Crew Members earn school-credited community service hours through day-of work: teaching outdoor skills at clinics, leading hikes, supporting trips for younger kids. Crew Leaders each own a named portfolio with real planning responsibility. Students train before they teach, including Wilderness First Aid certification, and scheduling stays flexible for athletes. Three commitments govern it: strictly volunteer, real ownership, counted impact. Schools, youth organizations, and outdoor businesses interested in partnering should write to us.
What’s next
The Northwoods returns. More experiences at Camp Highlands and smaller regional trips are in planning for 2027, and a multi-day pilgrimage walk in Japan on the ancient Kumano Kodo routes is in exploration for spring 2027. New expeditions are announced first through the Journal and the Trailhead Letter.
Bring Trailhead to your city
Trailhead started in St. Louis because that’s where its founder lives. The quiet distance isn’t local. Entrepreneurial communities everywhere, EO chapters among them, are full of tenured members and alumni who finished the first climb and are looking for the second.
Hosting a Trailhead experience looks like this: your people, a wild place within reach of your city, our structure and facilitation, costs shared at cost, nothing sold to anyone. If you lead a chapter, a forum, or a community of builders and want to talk it through, write to info@gotrailhead.com. You’ll hear back from a person.
The Trailhead Letter
Expedition announcements and each month’s essay, in your inbox. Nothing said in a Trailhead circle, and nothing for sale.
