Next Retreat is October 2 to 6, 2026
About Our 5 Day Retreats in Jackson, WY
Our retreat is for men ages 40–60 navigating transition including career shifts, relationship changes,
life transitions, or the quiet sense that something needs to change.​​
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This is a space to step away from the noise and gain clarity on what comes next.
Our signature program is a 5 day, 4 night secular retreat in Jackson, Wyoming
home of the majestic Teton Mountains.​​
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Who Is This For?
This is for you if:
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You’re navigating change and don’t want to drift through it
What used to drive you doesn’t anymore
You’ve built a good life, but it no longer feels like the whole story
You’re ready to decide what the next chapter looks like
What Happens
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Over five days in the Tetons, you’ll step out of routine and into structured reflection,
guided conversations, time in nature, and honest dialogue
with a small group of peers in similar seasons of life.
This is not religious. It’s not self-help hype.
It’s a deliberate pause to reset direction.
Space is limited.
We intentionally limit the group size to ensure depth, focus, and meaningful engagement.
If you’re ready to stop circling the question and start answering it, apply below.
Our next retreat: October 2 to 6, 2026.​
​If that sounds right for you, apply to join us.
Ooh man, it was incredible. The whole thing. It was all sort of unexpectedly overwhelmingly good." - Elliot
"It changed me. Improved me. Inspired me. Challenged me." - Rick
"Powerful. Game-changing. Eye-opening." - Chris
"While this may sound dramatic, it was life-changing." - Neil
Aside from the birth of my girls, the most influential experience of my life." - Kevin
Common Questions
Who joins one of your retreats?
Cairn & Sky is designed for men roughly 40–60 who are navigating a life transition — career shifts, relationship changes, new life-stages or a deeper question about what comes next.
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Is this a religious retreat?
No. Cairn & Sky is a secular retreat. While many men come with their own spiritual perspectives, the retreat itself is not affiliated with any religious tradition.
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What's the cost?
The cost is $3,095 and includes everything from the time we pick you up on Day 1 until we drop you off on Day 5. All food and beverages, local transportation, 4 nights accomodation, and activities are included.
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Is this group therapy?
No. This is not therapy. The retreat includes structured conversations, reflection, and time in nature, but it is not a clinical or therapeutic program.
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How many men attend each retreat?
We intentionally limit the group to about 8–12 men to ensure depth, trust, and meaningful conversation.
How fit do I need to be?
Our hikes can be challenging for some and we expect each guy to be reasonably fit. ​You don’t need to be an outdoorsman or athlete, but you should be comfortable hiking several miles and spending extended time outside. We move at a group pace and take breaks as needed. Many men find that the physical challenge is part of what makes the experience meaningful.
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What are the accomodations like?
We stay in rustic cabins with bunk rooms and shared bathrooms. We're not fancy. In this way, we keep the price affordable for more guys. Many guys find the simplicity helps them unplug and reset. The cabins are located in the National Park and the setting is both spectacular and allows easy access to trails.
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What does a typical day look like?
Each day includes guided conversations, time for reflection, hiking, and small group dialogue. There is also space for solitude and informal connection.​​​​
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What is your refund policy if I can't make it for some reason?
Because we keep group sizes small, deposits are non-refundable. If you need to cancel after registering, we’ll do our best to help you transfer your spot to a future retreat if space allows. Full details are available in our registration agreement.
