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Saddlebags to Surfboards: Kaleb's Life in Two Paradises

Born and raised amidst the rugged beauty of Skyline Guest Ranch, Kaleb has always placed priority on seeking adventure, exploration, and discovery. Growing up on the ranch, Kaleb's affinity for horses and adventure was evident from an early age. The vast expanse of Yellowstone National Park and the Beartooth Mountains became his playground, and the backcountry trails his second home. 


"Each journey through the rugged mountains of the Absaroka Beartooth Wilderness or the lush green valleys of Yellowstone fills me with gratitude and pride for the place I call home. I believe that Montana’s vastness, beauty, and atmosphere are unmatched by anywhere else on earth. However, at the end of each summer season I find myself packing my bags and saying goodbye to everything I knew growing up." 


Kaleb fell in love with Hawaii while on a family vacation to the Big Island. From that point forward, going to college and living on the islands was a goal he worked hard to achieve. After graduating from high school, Kaleb went to attend Brigham Young University- Hawaii on the beautiful north shore of Oahu. The transition from the rugged Beartooth Mountains of Montana to the tropical paradise of Hawaii was a stark contrast, but he embraced it wholeheartedly, eager to immerse himself in the vibrant culture and diverse landscapes of his new surroundings.


Within just a few days of being on the island, Kaleb realized his passion for surfing. It quickly became his go-to activity while on breaks from studies (maybe even in place of class and homework at times)! His list of hobbies rapidly expanded to include a myriad of adrenaline-fueled pursuits, from spearfishing to rock climbing, each one adding depth and richness to his already adventurous spirit. 


" My hobbies developed from snowboarding, snowmobiling, and flyfishing to surfing, diving, rock climbing and spearfishing. I spend most of my time at the beach surfing or playing in the waves. I love learning the culture, the language, and the customs. I have been blessed to meet local friends and families who have helped me learn and grow as a new member of the community. 

I often get asked the question “What do you miss about home” or “What do you miss about Hawaii”.  Because I am blessed to live in two very unique paradises, it's hard. I'm torn between two completely different worlds.


When I'm in Hawaii I miss a lot of things. I miss breathing cold air. I miss wearing sweatshirts and using blankets. I miss being able to see land as far as you can see. I miss being able to get in the car and drive forever on empty roads. Sometimes I forget how big home is compared to the island. I miss snowboarding and snowmobiling when I hear that there's good snow. I miss my horses and dogs and all of the wild animals we get to see regularly. And most of all I miss my family. I miss my mom and her home-cooked meals. I miss eating together each night laughing and joking with one another.  They are the people that truly know me best and I miss being with them. 

However, when I am at home I miss the ocean. I miss paddling out into good waves with great friends.  I miss the feeling right when the wave's energy gives you that push and you pop up and start barreling down the face of the wave. It's an adrenaline rush like nothing else I've ever experienced. I will never not want “just one more wave”. I often find myself watching surf videos and checking the surf cams. I  miss it being 80 degrees every day. I miss being tan and I miss going to the beach. 

These lists could go on and on forever. I truly love both of these places and am grateful to be able to split my time between them. Although I have definitely broadened my cultural knowledge and hobbies,  I love that I can stay true to my Montana-born upbringing. For the past 3 years, I have worked at two different ranches taking horseback rides, riding colts, and teaching others what I grew up doing. Guiding truly helps me stay connected to home and what made me the person I am today."


Each summer, as the school year ends, Kaleb returns to Skyline, ready to once again embrace his role as a backcountry fly-fishing guide. His transition from surfboard to saddlebag is always seamless as if he had never left the backcountry trails that had shaped him into the person he had become. 




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