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Tracking Your Wilderness: A 5-Day Men’s Retreat at Mount Shasta



Tracking Your Wilderness: A 5-Day Men’s Retreat at Mount Shasta
July 31 - August 5, 2026
Weed, CA, United States
5 nights, 6 days
25 person retreat
Highlights
Men’s Work
Connecting with the Land
Shadow Work
Wilderness Skills
Relational Healing
Unique and Beautiful Setting
Developing Community and Leadership
Tree Climbing and Fire-Making
Traditional Sauna
Trust-building Exercises
Local Food
Ecological Discovery
Gaining Self Knowledge
Details
Your next step is here. This retreat will bring you closer to your core, closer to the ground on which you walk, and to those who walk beside you. This retreat takes place in the pristine wilderness of Northern California, with a view of Mt Shasta. Streams of spring water flow throughout the land, for taking a morning cold plunge, or just listening to as you fall asleep in your teepee tent. Giant Doug Fir trees tower over the property, and the forest is host to bears, mountain lions, eagles, and beyond. Our intention is to bring men together to experience the raw and relational power of nature. This will be a unique combination of wilderness skills, cultivating presence, and establishing meaning and belonging amidst like-minded men. Three meals a day are cooked in the open air kitchen, and eaten outdoors by the river at picnic tables. We can accommodate all diets, and the food is prepared with love, and some of it comes straight from the organic garden on the property. The schedule is subject to change based on the groups needs. You can expect at least 1 wilderness skill workshop each day. The final night will be an optional solo on the land, to integrate your experience and perhaps answer any lingering questions you have in your life right now.
Venue
Headwaters Outdoor School
5 ★ 11 Reviews

At Headwaters Outdoor School in Northern California, we teach primitive skills to help people build a personal relationship with nature. Skills include Wilderness Living Skills, Nature Awareness, Earth Philosophy, and many others. We also offer custom classes for schools, groups, and individuals. Entering our primitive camp is like walking into a magical forest. You will cross over meandering creeks, some run full, allowing people to jump in the dipping holes, and some run at a steady trickle, inviting one to sit and get lost in the slower-than-slow pace. Our open-air camp kitchen and campfire area are the central meeting spaces between classes. Our tipi village consists of primitive, cedar bark shelters that were built in previous classes. There are also designated spaces for personal tents if you choose. There are also a few canvas tent cabins scattered throughout the camp.
Kitchen
Fire Pit
Bathroom
Accommodation
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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. Visitors encounter sacred spaces and signs of past guests—trails, art, and stories that enrich the experience. The Memorial Garden, nestled among manzanita and tall trees, honors lives that left lasting impressions. Fresh spring water flows through creeks and rivers, nourishing lush forests and wildflower meadows. Headwaters also features abundant food and flower gardens, including greenhouses, an orchard, and vibrant blooms that invite relaxation and reflection. With on-site amenities like hiking trails, hammocks, a sauna, and a nature library—as well as nearby adventures around Mt. Shasta—Headwaters offers both solitude and excitement for those seeking renewal. The teepee village consists of primitive, cedar bark shelters that were built in previous classes. These spaces will keep you dry, safe, and comfortable. Bring your favorite sleeping pad and bag. There is also a space to set up your tent if you prefer.
Meals

Meals provided
Breakfast · Lunch · Dinner
Diets catered
Vegetarian · Organic · Gluten-free · Nut Allergy Friendly · Dairy-free · Keto Friendly
Our gardens provide fresh, organic produce for meals and a space to unwind. With two greenhouses, an orchard, and thriving vegetable beds, we cultivate food that nourishes both body and soul. Meat provided from local farms perfectly complements the organic vegetables straight from the garden. Any dietary needs must be stated when a student signs up. The outdoor kitchen uses some primitive cooking methods to deliver delicious and nourishing meals throughout the day. You can taste the care that goes into all the grown vegetables. The food here is an absolute highlight!
Testimonials
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Host

Jesse Carter
Great Barrington, MA, USA
Jesse is a woodland wanderer, singer/songwriter, and world traveler always with an instrument. He believes in magic, and that sound and how we communicate have the power to awaken, transform, restore,...
4 languages
English, Español, Türk, and Français
Teaching for 5 years
Joined Insight Timer in Jul 2020
What's Included
Accommodation
Three delicious meals per day
Pristine Wilderness
Workshops led by experts in their field
Opportunities for ongoing connection
Integration call
Not Included
Transportation including airfare
Sleeping gear (sleeping bag, sleeping pad, and pillow)
FAQs
Guest requirements
Deposit and full payment due before arrival
Cancellation policy
The remaining balance for the retreat is due 90 days prior to the start date. If this balance is paid earlier than these 90 days, you are eligible to cancel and receive a full refund of this remaining balance, provided you do so at least 90 days before the retreat begins.
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