The next chapter starts outside.
Trailhead is built around the expedition. Several days somewhere remote enough that titles don’t survive the drive, built around morning circles that ask one hard question each. That’s where the deep work happens. Between trips, the community comes back together when there’s good reason to: a dinner, a reunion, a conversation built on thinkers like Richard Rohr, James Hollis, Parker Palmer, and Brené Brown. There’s no standing meeting schedule to keep up with. The friendships carry it.
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. Friendships formed on that trip, and the group still gathers from time to time. 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. Students train before they teach, earn school-credited service hours, and Crew Leaders own real pieces of the program. Three commitments govern it: strictly volunteer, real ownership, counted impact. Read about the Youth Crew →
What’s next
The Northwoods returns, and more experiences at Camp Highlands and smaller regional trips are in planning for 2027. One bigger idea is taking shape too: a multi-day pilgrimage walk on Japan’s ancient Kumano Kodo routes, timed to follow EO’s global conference in Kyoto in April 2027. It is still in development, and we’re telling that story honestly as it unfolds. Read about the Japan expedition →
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 new journal entries, in your inbox. Nothing said in a Trailhead circle, and nothing for sale.
