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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.

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.  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.

Can you share details about travel?

Our retreats start on Friday and end on Tuedsay. You'll fly into Jackson Hole (JAC) airport and we will pick you up and drop you off at the airport. Please arrive no later than 3 p.m. on Friday; and depart no earlier than 2 p.m. on Tuesday. Some guys choose to add a day on the front end and/or the back end. If you do that, we are happy to pick you up/drop you off at a hotel of your choosing close to the center of Jackson Hole. And, some guys also choose to make the drive to the retreat from their home. If so, please plan to arrive on location between 3:30 and 4 p.m. on Friday.

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.

What does a typical day look like?

Our days are long and satisfying. We typically rise for coffee and breakfast about 7 a.m. and end our days around a fire with a beer or soda about 9 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.

What happens before the retreat? Do I need to prepare?

A month before your retreat, you'll receive a journal and some questions to reflect on and write about. This reflection and writing is optional but intended to help you take advantage of our time together in person. Your Guides will also reach out to you to offer the chance to say hello and answer any questions you have. If you think the hiking may be especially challenging, we also suggest getting in better shape, in consultation with your doctor as needed. That's the prep you need.

How about after the retreat? Do you offer other programs?

About ten days after the retreat, we offer a group video call for guys to reconnect and to share how the return home is going for them. For an additional fee, we also offer regular monthly calls (for guys from our many retreats), an annual alumni gathering, typically in January/February, and one-on-one coaching.

What do I need to bring?

Here is a link to a suggested packing list. In short, bring yourself, a good pair of hiking shoes or boots, layers of clothing for a range of potential weather (warm and sunny, cold and rainy, even light snow), your journal (that we send you), and your toiletries.

What's the food like?

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/preferences (e.g. gluten-free, vegetarian, etc)

What is your refund policy if I can't make it for some reason?

If you cancel more than 60 days in advance, you will receive a full refund (less a 3% processing fee). Cancelations between 31 and 60 days prior to the retreat start will receive a 50% refund. Cancellation 30 days or fewer prior to the start of retreat are not eligible for a refund. If you need to cancel at any time, you also have the option of applying $2100 of your paid tuition to our next retreat, meaning you would need to pay an additional $995 to secure your spot.

What the hell is a cairn?

A lot of guys ask this question. It's a man made pile of stones to mark a trail or a place of significance. Even though it is not a well-known word, we encounter cairns on our hikes in the Tetons and we like how it relates to the metaphorical purpose and values of our retreats.

Contact
FAQs
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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