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EXPLORE YOUR PATH

Are you looking to write the next chapter of your life?
Wanting more meaning, connection, and joy?
Seeking adventure, laughter, and friendship?
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About Our 5 Day Retreats
in Jackson, WY

Our signature program is a 5 day, 4 night retreat near Jackson, Wyoming, close to the majestic Teton Mountains.

When you join us, you will gather with 6 to 10 other men of all ages and life-stages to hike among the incredible Tetons, reflect and journal on where you've arrived in life, challenge yourself, enjoy wisdom and support from your peers, have deep conversations, and share some laughs. It's regular men having an extraordinary experience.

If that sounds right for you, email or call us today.

Our next retreat: October 2 to 6, 2026.

Contact

In their words...

Here is what just a few of the many men who have joined us have said about their experience.

"While this may sound dramatic, it was life-changing." - Neil

 

"One of the most enlightening, rewarding, and amazing experiences."  - Heath

"Ooh man, it was incredible. The whole thing. The setting, the people, the structure, the physical and mental stretching and pushing, the organic opportunities to connect and learn and contribute, it was all sort of unexpectedly overwhelmingly good. It impacted me profoundly." - Elliot

"It changed me. Improved me. Inspired me. Challenged me." - Rick

"The experience was deep and meaningful in the connections I made with others, with myself, and with the outdoors" - Keith

"Powerful, game-changing, eye-opening." - Chris

"Aside from the birth of my girls, the most influential experience of my life." - Kevin

"Powerful. Game-changing.

Eye-opening."

 - Chris

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Frequently Asked Questions

Who joins one of your retreats?

We get men from across the country--23 states to date--and from a wide swath of careers: doctors, plumbers, tech execs, small business owners, attorneys, government workers, men in sales, education, the arts, and more. Most guys are between 35 and 65, though men in their 20s and 70s have also joined. They may be single, married, divorced or separated; with kids, without kids, empty-nesters.

What do guys have in common?

A desire to move forward in their lives, to get unstuck, to find connection. The guys who join us are willing to show up and engage, they are ready to explore what is true for them, and to be open to new friendships.​​ Also, the vast majority of men who join us have never been on a men's retreat before--this is new to them too.

What is 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. We will pick you up on Day One at Jackson Hole Airport, or the hotel of your choosing should you arrive earlier. And we will drop you off again at the airport or a hotel. All food and beverages, local transportation, 4 nights accomodation, and activities are included.

How hard is the hiking? How fit do I have to be?

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 5 to 10 miles each day. Jackson sits at about 6200 feet above sea level and our hikes go up from there. If you have concerns, we are happy to discuss them with you. Just reach out.

Reach out for more information

How to reach us:

Call or text us at 703.717.3603 or

Email us at Jerry@CairnAndSky.com or

Fill out our contact form.

Ready to join? Click here.

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