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.

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

📍 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.

📍 Jackson, Wyoming
📅 October 2–6, 20

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

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

01/27/2026

What is a day like at our retreat?

Our days are long and satisfying.

We stay in rustic cabins with bunk rooms and shared bathrooms. We’re not fancy.

We typically rise for coffee and breakfast about 7:00am, and end our days around a fire with a beer or soda about 9:00 p.m.

Each day includes some yoga in the morning, a facilitated conversation or activity, a hike, three meals, some down time to reflect or journal independently, and an evening session to share stories, insights, and laughs from the day.

Our hikes can be challenging for some, and we expect each guy to be reasonably fit. Our goal is to get you outside to have fun and explore beautiful places. Our hikes range in length from five to ten miles each day.

Sharing delicious meals together and staying fueled for our hikes is an important part of our time together. Food is provided by the chefs at Murie Ranch, our home for 5 days, and can cater to those with dietary restrictions and/ or preferences.

If this sounds like something you or a man you know would enjoy, please message! We’d love to connect!

01/20/2026

What the heck is a cairn??

A cairn is a pyramid of stones, assembled by explorers as both a landmark and a record of having been there. Over time, it becomes a collaborative act, each hiker adding a stone, extending guidance to those who follow.

Seen in landscapes around the world, cairns offer a metaphor for the sharing of knowledge: a quiet agreement among seekers to build upon what came before, so the path ahead is clearer for the next traveler.

01/12/2026

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

Our upcoming 5-day men’s retreat in Jackson, WY, near the majestic Teton Mountains, 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.

01/09/2026

5 Days. Big Mountains. Real Conversation…

If you’re interested in learning more about our October retreat, please drop your email in the comments and we will add you to our mailing list. 🏔️

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.

📍 Jackson, Wyoming
📅 October 2–6, 20

01/07/2026

5 Days. Big Mountains. Real Conversation.

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.

📍 Jackson, Wyoming
📅 October 2–6, 20

05/28/2024

The root of the word courage is couer - French for heart. And each of these guys brought so much heart to our time together in Jackson. Heart in what they shared with each other, in their kindness and compassion, in their resilience on some tough hikes, in their full throated laughter and big smiles, in their curiosity to learn about each other and themselves. I leave Jackson with a full heart and more faith in our capacity as men to live more emotionally full lives filled with greater connection and joy and response-ability.

10/04/2023

Thanks for a fun, connecting, challenging and meaningful few days together guys.

Address

13055 US 191
Jackson, WY
83001

Telephone

+17037173603

Website

http://www.CairnandSky.com/

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