Explore your path
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Break away from
your day to day. Gain elevation, perspective and insight. |
Our Retreats
Our signature program is our 5 day, 4 night retreat near Jackson, Wyoming. We base ourselves on a 64 acre ranch along the Hoback River, adjacent to three million acres of wilderness and 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.
Our signature program is our 5 day, 4 night retreat near Jackson, Wyoming. We base ourselves on a 64 acre ranch along the Hoback River, adjacent to three million acres of wilderness and 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.
"One of the most enlightening, rewarding and amazing experiences."
Heath, September 2022
Heath, September 2022
Who joins?
Our retreats serve a wide range of guys, from execs at Fortune 500 companies and stay-at-home dads, to small business owners and techies, to 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 retreats serve a wide range of guys, from execs at Fortune 500 companies and stay-at-home dads, to small business owners and techies, to 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.
Our retreats typically have between 7 to 11 guys and 2 guides. They're 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.
Our days include beautiful mountain hikes, facilitated discussions, relaxing down-time, some basic yoga, delicious shared meals, roaring fires, a bit of meditation and casual conversations.
If this approach to learning and growing seems right for you, join us.
Our retreats typically have between 7 to 11 guys and 2 guides. They're 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.
Our days include beautiful mountain hikes, facilitated discussions, relaxing down-time, some basic yoga, delicious shared meals, roaring fires, a bit of meditation and casual conversations.
If this approach to learning and growing seems right for you, join us.
2024 Retreat Dates
May 24-28, 2024 - Sold Out - Join us in September!
September 27-October 1, 2024
May 24-28, 2024 - Sold Out - Join us in September!
September 27-October 1, 2024
"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 |
Retreat 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's the price?
The price is $2,650 for 5 days and 4 nights. This includes all activities, local transport, accommodation, food and beverages. It doesn't include your flight to and from the Jackson area. Once you arrive (either a nearby airport or at the ranch itself if you are driving), you don’t need to spend another dime until you leave us.
Who goes on a retreat?
Each retreat has a maximum of 11 men and two Guides. Guys range in age from their 20s to 60s. Our retreat is a space to get some perspective. We may have stalled, stumbled, strayed, or even become a little lost on our life's path. We are looking for new insights to help us clear the brush and discover new possibilities. The challenges we face range from career, marriage or relationship, to family, self-worth, faith or health.
How hard is the hiking? How fit do I have to be?
You should be reasonably fit. Our goal is to get you outside to have fun and to explore beautiful places. Our hikes range in length from about 5 miles to 10 miles each, with some significant elevation change. We think most men who are reasonably fit can handle the hikes. We are happy to talk with you and answer any concerns you may have about your fitness for the experience.
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% or $75 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 $1800 of your paid tuition to our next retreat, meaning you would need to pay an additional $850 to secure your spot.
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's the price?
The price is $2,650 for 5 days and 4 nights. This includes all activities, local transport, accommodation, food and beverages. It doesn't include your flight to and from the Jackson area. Once you arrive (either a nearby airport or at the ranch itself if you are driving), you don’t need to spend another dime until you leave us.
Who goes on a retreat?
Each retreat has a maximum of 11 men and two Guides. Guys range in age from their 20s to 60s. Our retreat is a space to get some perspective. We may have stalled, stumbled, strayed, or even become a little lost on our life's path. We are looking for new insights to help us clear the brush and discover new possibilities. The challenges we face range from career, marriage or relationship, to family, self-worth, faith or health.
How hard is the hiking? How fit do I have to be?
You should be reasonably fit. Our goal is to get you outside to have fun and to explore beautiful places. Our hikes range in length from about 5 miles to 10 miles each, with some significant elevation change. We think most men who are reasonably fit can handle the hikes. We are happy to talk with you and answer any concerns you may have about your fitness for the experience.
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% or $75 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 $1800 of your paid tuition to our next retreat, meaning you would need to pay an additional $850 to secure your spot.
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 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 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 text him on 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 text him on 617-599-0468 and share your name and any questions you may have about Cairn & Sky.