July 31 - August 5
Tracking Your Wilderness: Mount Shasta, CA
Through immersive workshops and skill-building practices that awaken both soul and senses, you'll uncover the patterns that shape how you move through the world. Learn to take each step from your center. Tune into your instinct. Practice leading yourself and others with clarity and integrity.
❋ Wilderness and survival skills training
Wilderness-based offerings may include: Rewilding Education, Animal Tracking, Vision Quest, Camouflage, etc.
Daily movement and embodiment practices. Participant-led Workshops.
❋ PRACTICEThree healthy, organic meals per day. Rest, journal, read, or explore the land.
❋ NourishmentTopics may include: Integrity in Relationship, Breathwork, Trusting More & Controlling Less, Leading from Your Core, Facing Your Shadow, and more.
❋ Expert Facilitation
What happens in the wilderness changes you. It brings you closer to yourself, to those you love, and to the deeper purpose you carry. And when we do this work in community, something powerful takes root: those who witness us become our brothers. 2026 ROADMAP
DATES
July 31 — August 5
PRICING
$2,250
Payment plans are available at check-out.
Limited scholarships available upon request. Don’t let finances be the reason you don’t reach out. We’re here to work with you.
What’s Included
Lodging (wooden teepee or outdoor camping)
Three healthy, organic meals per day
All guided experiences, teachings, ceremonies, and materials
What’s NOT Included
Travel to and from Headwaters Outdoor School
Tips for Headwaters Staff
DETAILS
Location: Headwaters Outdoor School — nestled at the base of majestic Mt. Shasta
Accommodations: Stay in rustic wooden teepees or sleep under the stars on the land
Meals: Enjoy three wholesome organic meals per day, prepared with care and intention
Experiences Included
Wilderness and survival skills training
Animal tracking practices
Traditional sweat lodge ceremony
Daily time in nature focused on presence, relationship, and embodiment
Transportation
Possible shuttle option available from a nearby airport (details upon registration)
If you are flying cross country, consider landing in Medford, Oregon or Redding, California (1.5 hour drive).
Day One — July 31st 4-6PM: Arriving
Afternoon arrivals to Mount Shasta, CA.
Settling in, opening circle late evening
Days Two, Three, Four, Five — August 1 - 4th: Daily Practices
Breakfast, Lunch, Dinner
Land Adventure Activity
Movement
Rewilding Education
Participant-led Workshops
Day Six — August 5th: Departing
Morning Departures
OVERVIEW
SAMPLE SCHEDULE
Final schedule will be confirmed closer to the event date.
Optional Movement or Sitting Meditation7:00 – 7:30am
BREAKFAST8:00 – 9:00am
MORNING WORKSHOP9:00 – 11:30am
LUNCH12:00 – 1:00pm
FREE TIME1:00 – 2:30pm
afternoon workshop2:30 – 5:30pm
DINNER5:30 – 6:30pm
evening circle7:00 – 8:00pm
THE INVESTMENT
$2,250
TESTIMONIALS
“This retreat was a powerful reset that left me feeling energized, refreshed, and inspired. The Headwater Outdoor School is a magical forest at the base of Mt. Shasta, and I felt deeply connected to the water, the trees, and living creatures that engulfed my surroundings. I enjoyed the various activities that both broadened my outdoor wilderness skills and sharpened my philosophies on being a man. It was comforting to be around a group of men that shared a willingness to be open to anything and everything, as well as the ability to listen and be heard.”
- Rich C, 2025 Tracking Your Wilderness Attendee
“POWERFUL RESET”
“LIFE CHANGING”
“The setting was incredible, unique, and magical in itself. What jumps out the most about the experience is the sense of connection. Everyone brought it - full send. The example set by our leaders, who were both full participants & guides, really set the tone. They fostered an environment where all had the courage to be vulnerable, to trust, and to authentically share. The result was dramatic, I suspect life changing for most everyone.”
- Chris C, 2025 Tracking Your Wilderness Attendee
“The reflection and retreat exercises were great… and a perfect balance to the wilderness skills that Headwaters was teaching.”
- Rich C, 2025 Tracking Your Wilderness Attendee
“PERFECT BALANCE”
““15 guys climbing high into a 125 foot Douglas Fir Tree at the same time was a combination of a meaningful group activity, a strong connection to nature & a return to the wonders of childhood.”
— Chris C, 2025 Tracking Your Wilderness Attendee
“CONNECTION TO NATURE”
THE LOCATION
Headwaters is a peaceful sanctuary nestled at the base of the Eddy Mountain Range, offering the natural beauty of a national park without the crowds. Spanning 144 acres of meadows, forest, and flowing waters, it borders the Shasta-Trinity National Forest and is home to abundant wildlife and serene landscapes. Once inhabited by the Klamath and Shasta tribes and later impacted by logging, ranching, and wildfires, the land is now lovingly restored and carefully managed to balance fire resilience with natural beauty, creating a place of refuge, discovery, and deep connection to nature.
Headwaters Outdoor School
THE LEGEND
Commune with the Founder of Headwaters Outdoor School
TIM CORCORAN
Tim’s Irish heritage, as taught to him by his uncle and his grandfather, has linked him deeply to Earth peoples’ philosophy of life.
He first went to the woods at age six and began communicating with the spirits of animals. He knew then that this was his home. At seventeen, Tim spent four months alone in the Canadian Wilderness practicing Earth living skills.
GUIDES
Kenny is an Executive Coach and menswork facilitator who supports business leaders in navigating life’s complex challenges in the pursuit of their highest potential. His mission is to guide a new era of leaders in enhancing their capacity, depth, resilience, and authenticity, thereby amplifying their impact on the companies, communities, and families they lead.
Kenny brings 15 years as a startup CEO and 2,000+ hours coaching founders and professionals — from early-stage startups to Fortune 100 companies, including Apple, Google, and Amazon. His coaching integrates vision, strategy, and execution with the deep personal work of aligning mind, body, and spirit to catalyze clients’ leadership and influence so they’re no longer forcing outcomes, but magnetizing them.
KENNY BORG
Jesse has been deeply involved in men’s work for 7 years, when a relationship ended and he fell into a local men’s group who supported him through. He is currently a Gestalt and Sensorimotor psychotherapist in Massachusetts, and has an international following on Insight Timer for his guided yoga nidras. He is pursuing an equine and nature psychotherapy certification with Duey Freeman in Colorado.
Some of the most pivotal moments of his life have arisen from extended time in the wilderness: in the mountains and rivers of North Carolina, the Maine coast with Outward Bound, summers in the Adirondack wilderness, walking the Camino de Santiago, the Lycian Way, the Annapurna Circuit, backpacking in Patagonia, and beyond. Trail running on the Appalachian Trail is his current favorite outdoor pursuit.
JESSE CARTER
Nick holds a Masters of Clinical Psychology and Counseling, specializing in transpersonal nature based therapy. As a Gestalt Equine Psychotherapist, Nick integrates therapeutic work with horses to facilitate deep emotional healing. A lifelong outdoorsman and Eagle Scout, he is also a trained wilderness first responder. Nick leads international off-grid sailing expeditions, through his program, This is Water, combining his love for adventure with a commitment to personal growth and transformation in nature.
Nick leads several men’s groups weekly, serves as the primary therapist at a recovery center, and is a frequent public speaker. He has taken hundreds of folks on journeys to explore their inner wildness with the support of the external wilderness. The two are not that different. His pal Jesse Carter introduced him to men’s work 5 years ago.
NICK SHARP
Jeremy's love for the outdoors, personal growth, and connection to the natural world was nurtured from a young age through family adventures that sparked a lifelong passion. Since then, he has been actively engaged in nature, education, and exploring new ways of relating to the Earth with greater presence and intention.
Through a wide range of explorations, challenges, and meaningful encounters, Jeremy has discovered a depth of connection and guidance in the natural world beyond what he ever imagined. He holds a deep belief that our progress as a species depends on our ability to repair and restore our relationship with the environment—collectively, ceremonially, and consistently.
Currently based in Lafayette, Colorado, Jeremy works as a therapist while continuing to expand his own practices and awareness around the disconnection between where we are now and the path forward toward ecological and spiritual alignment.