What am I becoming?
Asked on the first morning of the Northwoods retreat, Plum Lake, August 2026.
Trailhead takes small groups of people into the wilderness and asks them questions they have stopped asking themselves. Then it keeps them in each other’s company for the year after.
What this is
Most of the people who come to Trailhead have already built something. A company, a firm, a practice, a family, a reputation. The building worked. Somewhere along the way, though, “more” quietly stopped being an answer and became a habit. Trailhead is for that moment.
It is not a retreat in the spa sense and it is not a leadership seminar. It is several days somewhere remote enough that your title does not come with you. Morning conversations that ask one hard question each. Afternoons on the water or the trail. Evenings around a fire. The wilderness is not the backdrop. It is the mechanism. When the professional context is stripped away, people say things they have not said out loud in years.
Trailhead began with men navigating midlife transitions. Its expeditions welcome men and women.
The trail so far
The Northwoods Wilderness Retreat. August 2026, Camp Highlands, Sayner, Wisconsin. Seventeen campers spent five days on Plum Lake with three morning questions, canoes, portages, and a sunrise most of us will remember longest. Read what happened.
Trailhead Youth Crew. An outdoor leadership program for high school students, launching January 2027. Crew Members earn school-credited service hours teaching outdoor skills to younger kids. Crew Leaders own real portfolios. Students train first, including Wilderness First Aid certification, and the program culminates in a major camper trip in June 2027. Schools, youth organizations, and outdoor businesses interested in partnering are welcome to write.
What comes next. More experiences at Camp Highlands and smaller regional trips are in planning for 2027. A multi-day pilgrimage walk in Japan, on the ancient Kumano Kodo routes, is in exploration for spring 2027. Details will appear here when confirmed.
Three questions
Every Trailhead expedition is built around morning sessions, each organized around a single question. What am I becoming? What have I been carrying? What am I choosing not to see? The questions do not change much from trip to trip. The answers do.
The Journal
Each month we publish an essay on the work of the second half of life: purpose, discomfort, relationships, money, meaning, and the questions underneath all of it. Honest, sometimes hard to hear, always written from inside the climb.
The Trailhead Letter
A short letter, sent when there is something worth sending. Each new journal entry, reading worth your time, and news when the next group heads for the trees. Never anything said in a Trailhead circle, and never a sales pitch, because there is nothing to sell.
Two commitments
Trailhead is a nonprofit. Go Trailhead, Inc. is a Missouri nonprofit corporation with 501(c)(3) status in process. No one is paid. Expedition costs are shared at cost among campers.
What is said in a Trailhead circle stays in the circle. That is the first thing we say on every expedition and the last thing we say before we leave.
Trailhead · St. Louis, Missouri · info@gotrailhead.com
