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

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

July 31 - August 5, 2026

Weed, CA, United States

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Hosted By

Jesse Carter

2.3k followers

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5 nights, 6 days

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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.

Location

Weed, CA, United States

Weed, California, is a small town nestled in the shadow of Mount Shasta in Siskiyou County, known for its stunning natural surroundings and rich history. Originally established as a lumber town in the late 1800s, Weed retains its rustic charm while offering a gateway to the outdoor adventures of Northern California. The town is a popular stop for travelers exploring the Pacific Northwest, providing easy access to activities such as hiking, fishing, and skiing in the nearby Shasta-Trinity National Forest. Weed's quaint downtown area features local shops, cafes, and the Weed Historic Lumber Town Museum, which offers insights into the town's logging heritage. With its picturesque setting and welcoming community, Weed serves as a charming and convenient base for exploring the breathtaking landscapes and recreational opportunities of the Mount Shasta region.

Venue

Headwaters Outdoor School

5 11 Reviews

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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

Kitchen

Fire Pit

Fire Pit

Bathroom

Bathroom

Accommodation

Tipi

2-person shared room

$1,980 USD / person

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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

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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!

Schedule

Sample schedule: (Exact schedule to be determined closer to start date.) 7-7:30 AM: Moving or Sitting meditation (Optional) Breakfast: 8-9 AM Morning Workshop: 9-11:30 (Men’s workshops include: Integrity in Relationship, Making Contact, Trusting your Team, Leading from your Core, Facing your Shadow, etc…Wilderness-based workshops include: Animal Tracking, Camouflage, Vision Quest, Sauna, etc) Lunch 12-1 1-2:30 Free time for rest, journaling, reading, wandering the land, etc 2:30-5:30 Afternoon Workshop 5:30-6:30 Dinner 7-8 Evening Circle Be aware that this schedule is subject to change in relationship to what is unfolding on any particular day. We will email you with a more detailed schedule as the retreat nears.

Testimonials

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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, United States

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Host

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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.