Cairn & Sky

Cairn & Sky Retreats for men in Jackson Hole, Wyoming. Explore your path.

We bring together guys of all ages and life-stages to pause, reflect, laugh, hike, connect and discover new capabilities and possibilities for themselves.

06/21/2026

Happy Father’s Day from Cairn & Sky 💙

A retreat can be a powerful experience and we believe that if you are a guy with some questions, challenges, or dilemmas in his life, you will very likely benefit from joining us in Jackson.

If you are the spouse or partner of a guy like that—or the sibling, parent, or child of that guy—we think you will see how the retreat has benefited the man you love.

OUR NEXT RETREAT IS OCTOBER 2nd-6th

06/08/2026

Do you know a man craving deeper connection, clarity, and real friendship?

Our upcoming 5-day men’s retreat in Jackson, WY—set near the Tetons—is an invitation to slow down, reflect, and reconnect with what matters.

Small group. Big landscapes. Honest conversations.

If someone you care about is searching for purpose and community, please share this with him.

06/08/2026

Do you know a man who could benefit from deeper connection, clarity, and friendship? Our upcoming five-day, four-night retreat in Jackson, Wyoming, near the Teton Mountains, offers space to step back, reflect, and explore a more grounded, intentional path forward.

Jerry and Scott founded Cairn & Sky in 2022 because we were seeking these same things. We believe we can help other men find them as well.

In the last three years, dozens of men have joined us on the trail and around the fire.

The retreat is a gathering of six to ten men of all ages and life-stages invited to hike among the incredible Tetons, reflect and journal on where they’ve arrived in life, challenge themselves, enjoy wisdom and support from peers, have deep conversations, and share some laughs.

If someone you care about is searching for greater purpose, connection, and community, this retreat may speak to him. Please share this invitation to explore a more meaningful path.

Cairn & Sky is excited to share an opportunity for growth with practitioners we deeply respect: Bob Soulliere and Jerry ...
03/24/2026

Cairn & Sky is excited to share an opportunity for growth with practitioners we deeply respect: Bob Soulliere and Jerry Hill.

Breath and movement aren’t techniques to master, but the body’s most direct way to settle, organize, and restore trust. When they work together, effort softens and awareness sharpens.

Join them for the Durable Foundations Retreat (Primal Movement)
May 31–June 5 | Omega Institute, Rhinebeck, NY

Five days of accessible breathwork and natural movement to reduce tension, restore clarity, and build a grounded sense of presence. This work is not about pushing limits, but meeting each moment with more ease and responsiveness.

You’ll leave with practical tools to regulate, move with confidence, and stay oriented as life unfolds.

Link in bio to learn more and register

Cairn & Sky occasionally collaborates with practitioners doing truly incredible work and today we’re honored to share ou...
03/19/2026

Cairn & Sky occasionally collaborates with practitioners doing truly incredible work and today we’re honored to share our friends at Sacred Wyld

Based in Arizona, Sacred Wyld is stewarded by Wes Atkinson, a career hunter and guide, and Joanna Kraft, an artist and former farmer devoted to sustainable food systems.

Together, they guide individuals and communities into more conscious, reciprocal relationships with the animal kingdom (especially the animals that nourish us).

Through educational experiences, rites of passage, and a private membership program, they’re helping restore reverence to the way we source and share food.

On our recent Sedona retreat, Sacred Wyld nourished our group of 14 men from sunup to sundown with deeply intentional meals. Beyond the food itself, Joanna and her team brought a powerful presence into the kitchen, creating a space for connection, gratitude, and a deeper understanding of what it means to truly be fed.

We are grateful for the work they’re doing.

Please reach out to them directly to learn about their upcoming events.

Cairn & Sky offers nature-based retreats for men in beautiful Jackson Hole, WY.Our retreats bring together guys of all a...
03/07/2026

Cairn & Sky offers nature-based retreats for men in beautiful Jackson Hole, WY.

Our retreats bring together guys of all ages and life-stages to pause, hike, reflect, laugh, connect and discover new possibilities for themselves.

We have limited spots available for our next retreat October 2nd-7th 2026.

If you’re interested or know a guy who might be, please reach out via DM.

Explore your path.

02/24/2026

Co-founder and retreat facilitator Scott Taylor tells us a bit about his “why?”

Our signature 5-day / 4-night retreat takes place near Jackson, WY, in the shadow of the Tetons.

You’ll join a small group of 6–10 men—across ages and life stages—to hike, reflect, journal, challenge yourself, and talk honestly about where you’ve been and where you’re going. Expect meaningful conversations, peer wisdom, laughter, and space to reset.

Regular men having an extraordinary experience.

Please message us with questions.

jacksonholeretreat

đź“Ť Jackson, Wyoming
📅 October 2–6, 2026

02/17/2026

Co-founder & retreat leader shares his “why”?

Our signature 5-day / 4-night retreat takes place near Jackson, WY, in the shadow of the Tetons.

You’ll join a small group of 6–10 men—across ages and life stages—to hike, reflect, journal, challenge yourself, and talk honestly about where you’ve been and where you’re going. Expect meaningful conversations, peer wisdom, laughter, and space to reset.

Regular men having an extraordinary experience.

Please message us with questions.



đź“Ť Jackson, Wyoming
📅 October 2–6, 20

WHY a men’s retreat?The benefits of our retreat to Jackson are too many to name and each guy will discover different one...
02/11/2026

WHY a men’s retreat?

The benefits of our retreat to Jackson are too many to name and each guy will discover different ones—the chance to destress and reset; the chance to enjoy the outdoors; the chance to reflect, journal, and be quiet; and many more.

Two of the biggest and most consistent take-aways, however, are friendships and insight.

It’s remarkable the bonds of friendship you can create on an intentional five day retreat and the unexpected insights you can draw—insights that before retreat you may have thought were unrelated to the questions and challenges in your life; but which on retreat, you realize are actually fundamental to those questions and challenges—right at their beating heart.

A retreat can be a powerful experience and we believe that if you are a guy with some questions, challenges, or dilemmas in his life, you will very likely benefit from joining us in Jackson. If you are the spouse or partner of a guy like that—or the sibling, parent, or child of that guy—we think you will see how the retreat has benefited the man you love.

OUR NEXT RETREAT IS OCTOBER 2nd-6th

Twelve of our C & S Jackson, WY retreat alumni have just returned from an extraordinary retreat to Sedona, Arizona.The f...
02/03/2026

Twelve of our C & S Jackson, WY retreat alumni have just returned from an extraordinary retreat to Sedona, Arizona.

The four day adventure featured hiking amongst incredible views, deep conversation and connection, and lots of laughs.

Our days included not only superb hiking, but also introductory yoga classes to get our bodies moving, and conversations that allowed guys to connect on the things that matter most to them - family, relationship, career, faith, friendship.

Alumni retreats like Sedona include the essentials of our Jackson retreats — yoga, mindfulness, great food, deep conversation, and gorgeous hikes through mind-blowing natural beauty — but are designed for guys who already have experienced the transformative experience of Jackson.

OUR NEXT RETREAT TO JACKSON, WY IS OCTOBER 2ND-6TH, 2026


Address

13055 US 191
Jackson, WY
83001

Telephone

+17037173603

Website

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