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Our Programs
The Retreat; a place to connect and reflect
Our signature program is our 5 day, 4 night retreat near Jackson, Wyoming close to the majestic Teton Range.
Here small groups of men of all ages and life-stages gather to pause, reflect, laugh, hike, connect and discover new possibilities for themselves.
Fall Retreat Dates: October 1-5, 2025
August 31 Deadline to Join
Our signature program is our 5 day, 4 night retreat near Jackson, Wyoming close to the majestic Teton Range.
Here small groups of men of all ages and life-stages gather to pause, reflect, laugh, hike, connect and discover new possibilities for themselves.
Fall Retreat Dates: October 1-5, 2025
August 31 Deadline to Join
Have questions? Want to learn more?
Email Scott at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 617-599-0468 and share your name and any questions you may have about Cairn & Sky.
Email Scott at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 617-599-0468 and share your name and any questions you may have about Cairn & Sky.
"One of the most enlightening, rewarding and amazing experiences."
Heath, September 2022
Heath, September 2022
Who joins?
Our programs serve a wide range of guys of all ages and life-stages. We have execs and engineers at Fortune 500 companies to stay-at-home dads and retirees. We have small business owners and craftsman, entrepreneurs and creatives. Guys who are single, married, divorced, and separated. Guys with kids, without, and empty-nesters.
What really matters?
The thread that connects us is we're all working on something in our life. For some it's our relationships with our partners, spouses or family members. Or it's our careers, passions and purpose. For others it's our friendships and community or we're in a moment of transition in our lives.
What really matters is you're open to exploring what's true for you, to creating new friendships with other guys, and you're willing to show up and engage.
Our programs serve a wide range of guys of all ages and life-stages. We have execs and engineers at Fortune 500 companies to stay-at-home dads and retirees. We have small business owners and craftsman, entrepreneurs and creatives. Guys who are single, married, divorced, and separated. Guys with kids, without, and empty-nesters.
What really matters?
The thread that connects us is we're all working on something in our life. For some it's our relationships with our partners, spouses or family members. Or it's our careers, passions and purpose. For others it's our friendships and community or we're in a moment of transition in our lives.
What really matters is you're open to exploring what's true for you, to creating new friendships with other guys, and you're willing to show up and engage.
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"The experience was deep and meaningful in the connections I made with others, myself and with the outdoors" - Keith |
Space is very limited.
We keep groups small on purpose.
Our group size creates the space for you to explore what’s relevant and valuable for you given your unique story and life experience. It also supports deeper connection with your fellow guys.
If this approach to learning and growing seems right for you, join us.
We keep groups small on purpose.
Our group size creates the space for you to explore what’s relevant and valuable for you given your unique story and life experience. It also supports deeper connection with your fellow guys.
If this approach to learning and growing seems right for you, join us.
2025 Retreat Details
The Retreat
A one-time opportunity to pause, reflect, connect and imagine new opportunities with a small group of guys in a beautiful place.
Dates: October 1-5, 2025
Key Elements
Enrollment: Only 10 spaces available
Deadline to Join: August 31
Pricing: $2,995
A one-time opportunity to pause, reflect, connect and imagine new opportunities with a small group of guys in a beautiful place.
Dates: October 1-5, 2025
Key Elements
- A 5-day, 4 night in person retreat for you to consider who you are and where you in your life, to do some beautiful hikes, to share your story and listen to others, to work on a dilemma or challenge you're facing and to explore what's possible for your life.
Enrollment: Only 10 spaces available
Deadline to Join: August 31
Pricing: $2,995
- Includes all programming and materials as well as food and lodging on retreat. Doesn't include travel to and from our retreats.
"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, September 2022
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"Powerful, game-changing, eye-opening" - Chris, May 2022 |
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"Aside from the birth of my girls, the most influential experience of my life" - Kevin, September 2021 |
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"While it may sound dramatic, it was life-changing" - Neil, May 2022 |
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"It changed me. Improved me. Inspired me. Challenged me. " - Rick, September 2022 |
FAQs
What the hell is a cairn?
A lot of guys have asked this question. It's a man-made pile of stones used to mark a trail or a place of significance. Even though it's not a well-known word, we encounter cairns on hikes in the Tetons and we like how it relates to the metaphorical purpose and value of our retreats.
What are the accommodations like?
We stay in rustic cabins with bunk rooms and bathrooms. We aren't fancy which is one way we try to keep the price affordable for more guys.
What's a typical day look like?
Our days are long and satisfying. We typically rise for coffee around 7 AM and end our days around a fire with a beer around 9 PM. Each day includes some yoga in the mornings, 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 laughter 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 is optional but intended to help you take advantage of our time together in person. Your Guides also will reach out to you to offer the chance to say hello and answer any questions you have. That’s all the prep you need.
What do I need to bring?
Here is 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 or and even light snow), and your toiletries.
What's the food like?
Sharing delicious meals together and staying fueled up for our hikes is an important part of our time together. While our menus will vary, we provide breakfast, lunch and dinner, try to source local and organic ingredients as much as possible and make sure dietary restrictions are accommodated.
What's 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). Cancellations between 31-60 days prior to the retreat will receive a 50% refund.
Cancellations 30 days or less prior to the start of your retreat are not eligible for a refund.
If you need to cancel at any time you have the option of applying your paid amount to the next date of the same program.
What the hell is a cairn?
A lot of guys have asked this question. It's a man-made pile of stones used to mark a trail or a place of significance. Even though it's not a well-known word, we encounter cairns on hikes in the Tetons and we like how it relates to the metaphorical purpose and value of our retreats.
What are the accommodations like?
We stay in rustic cabins with bunk rooms and bathrooms. We aren't fancy which is one way we try to keep the price affordable for more guys.
What's a typical day look like?
Our days are long and satisfying. We typically rise for coffee around 7 AM and end our days around a fire with a beer around 9 PM. Each day includes some yoga in the mornings, 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 laughter 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 is optional but intended to help you take advantage of our time together in person. Your Guides also will reach out to you to offer the chance to say hello and answer any questions you have. That’s all the prep you need.
What do I need to bring?
Here is 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 or and even light snow), and your toiletries.
What's the food like?
Sharing delicious meals together and staying fueled up for our hikes is an important part of our time together. While our menus will vary, we provide breakfast, lunch and dinner, try to source local and organic ingredients as much as possible and make sure dietary restrictions are accommodated.
What's 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). Cancellations between 31-60 days prior to the retreat will receive a 50% refund.
Cancellations 30 days or less prior to the start of your retreat are not eligible for a refund.
If you need to cancel at any time you have the option of applying your paid amount to the next date of the same program.
FOUNDERS
Cairn & Sky was born from our desire for more connection, adventure and community in our lives and we thought other men might want more too.
Scott Taylor
Scott has been in the learning and leadership development space for over 20 years and has led programs for men since 2016. He's been an executive in the private and non-profit sectors, an outdoor educator, a Peace Corps Volunteer and a consultant and leadership coach. He has trained in life and executive coaching with Co-Active Training Institute. Scott holds a masters degree from Harvard, loves cycling trips in Europe, a smooth bourbon, the stillness of mornings and his dog Weezie.
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Jerry Casagrande
Jerry is a social entrepreneur and writer. He's launched a couple of organizations, written and produced screenplays, and worked in international development. He's lived in Mongolia and Costa Rica and got his MBA from Stanford back in the day. He has trained in positive psychology coaching with The Whole Being Institute. Jerry is married with three kids and loves spending time on Lake Joe in Canada, dipping into freezing lakes, rivers (or even buckets), and hanging with his dog Lucy.
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Have questions? Want to learn more?
Email Scott at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 617-599-0468 and share your name and any questions you may have about Cairn & Sky.
Email Scott at [email protected] and he'll be in touch within 24 hours.
Or you can call or text to 617-599-0468 and share your name and any questions you may have about Cairn & Sky.