The Mother-Son Summit: Kristin & Simon’s Kilimanjaro Adventure
Some climbs are about summits. Others are about stories, and the people you share them with.
For Kristin and her 12-year-old son Simon, their Kilimanjaro expedition became both a test of endurance and a shared journey between mother and son that changed how they see each other, and the mountains, forever.
They trained side by side for months—running, hiking, and swimming—trading weekends with friends and dive competitions for long miles under heavy packs. It was the first time they had ever trained for something together, and the shared challenge brought them closer in ways neither had expected.
Preparing from their low-altitude home, they improvised, with heat replacing thin air and determination replacing elevation. To simulate altitude before the trip, they flew to Colorado to hike a 14er. When a snowstorm swept in near the summit and they sheltered in a rock cave, they realized they were learning lessons far bigger than fitness. Kristin recalls the learning curve they had to adapt to, such as when to keep pushing, when to pause, and, of course, when to turn around.
Alongside them was CTSS guide Pega Sherpa, an eight-time Everest summiter known for his quiet strength, humility, and generosity. His steady presence on the mountain would become a defining part of their experience, and a friendship that’s lasted long beyond the climb.
These moments brought this mother-and-son duo closer, shaping the bond that would carry them to the Roof of Africa.
Kristin, how did it feel to be standing on the summit, staring out at the roof of Africa together?
“It was overwhelming. We were both in tears from the relief and wonder of actually realizing our dream. Simon had pulled ahead of the group with Mary, our head Tanzanian guide, and I watched from a distance to see him approaching the summit.
For me, it was one of the most emotional experiences of my life, something I compared only to childbirth. To watch my son, who had nurtured a dream from a seed to its completion, in the protective hands of a team of adept mountaineers—it was truly soul-filling. The team was so supportive of both of us, but they picked Simon up in the air, whooping and celebrating his victory. It was such a beautiful thing, full of pride, joy, and the relationships that had developed through such an intense and amazing feat.”
Before that moment on the summit, the real work began long before they reached Africa. Kristin and Simon shared what it was like to train together for Kilimanjaro.
“The process definitely brought us closer, as we had never trained for anything together up until that point. There were weekends when, instead of spending time with friends or competing on the dive team as in summers past, we went out for solo hikes, runs, or swims. Living at low altitude, we had to get resourceful—carrying heavy packs, hiking up to fifteen miles in the heat, and eventually flying to Colorado to hike a 14er to simulate altitude. There was a real learning curve with gear and pacing—when to push through and when to pause and reassess. Those challenges brought us closer and prepared us for the unknowns of Kilimanjaro.”
Shared Summits, Shared Generations
Kristin and Simon were not the only family team on the summit of Kilimanjaro that day. A father–daughter duo also shared the trail with them, adding to the sense of community that makes CTSS climbs so special. Watching different generations move toward the same goal brought something unique to the mountain, a reminder that adventure has the power to connect us at any age.
At CTSS, we’ve seen this again and again. Intergenerational climbing has become one of the most inspiring themes across our expeditions, and for good reason. Research shows that engaging in outdoor activities together across generations strengthens family bonds, communication, and mutual understanding. On the mountain, those benefits come to life in real time. Families learn to move at each other’s pace, trade leadership, and rediscover the value of shared challenge.
This year alone, we’ve seen that spirit unfold across continents. Emma and Sam Schwerin have climbed side by side from Ecuador, Kilimanjaro, and Mont Blanc to Denali, Aconcagua, and Everest, where Emma became the youngest American woman ever to reach the summit. Their journey to complete the Seven Summits has been a shared pursuit from the very beginning, a testament to how partnership and family can carry you to the world’s highest places. Also in Nepal, but on a different journey, Ethan Ong and his father, Harold Ong, took part in our Rugged Luxury Everest Base Camp Trek and Stay, where Ethan not only completed the trek to Everest Base Camp but also raised more than $9,000 for the Tendi Sherpa Foundation, proving that purpose and adventure can go hand in hand.
For Kristin and Simon, Kilimanjaro became part of that same story. Their climb reflected what we believe at CTSS: that the mountains are more than destinations. They are classrooms for patience, trust, and teamwork, places where generations come together to learn from each other, supported by guides who embody that same spirit of belonging and shared purpose. Our world-class team doesn’t just lead the way; they walk beside you, helping each climber find confidence that lasts long after the descent.
You climbed alongside Pega Sherpa, one of our top Everest guides. Simon, what did you learn from his leadership and experience on the mountain?
“Pega was so amazing. He told me about all kinds of different mountains he had climbed or wanted to climb in the future. I asked him so many questions about Everest and the Himalayas.
One day, my sleeping mat popped, and Pega gave me his because he said he didn’t need it. On summit day, he helped me feel better and told me to put on a hat because my head hurt. Five minutes later, my headache was gone. I just can’t believe how many mountains he’s climbed. He’s such an amazing guide, and I hope to climb with him again.”
For Kristin, watching Pega guide her son was something she’ll never forget.
“Pega was an incredible leader. He has an extensive mountaineering skillset, including hundreds of technical climbs throughout Nepal and eight Everest summits. Where some people might develop an ego around such mastery, Pega was the opposite—always humble, always calm, always helpful.
He carried our heavier items to lighten our load, lent us his sleeping mat when ours popped, gave Simon inspiring advice, taught him card tricks, checked our oxygen levels and heart rates every night before bed, and made us laugh.
We were all in tears when we had to part ways. We’re sure we’ve made a friend for life in Pega and continue to stay in touch. Simon follows Pega on Instagram and loves seeing his radical climbs throughout Nepal.”
Beyond the climb itself, you also experienced Tanzania—the food, the culture, and even waterfall and village tours before the expedition. Kristin, what stood out to you most?
“We spent a lot of time in the van traveling from place to place, and it gave us an opportunity to observe people we would never have seen otherwise. We were amazed to see young children walking unaccompanied to and from school, sometimes in uniforms, along busy highways.
The porters were incredible athletes, carrying up to twenty kilograms each day and arriving to camp hours before us. Other children had built toys out of bottle caps and scraps—showing such creativity and resilience.
At a coffee farm, we saw an extended family running the business together from plant to roast to sales, with song woven into every part of the process. That same joy and music carried us up the mountain on summit night. Whenever I felt overwhelmed, our guides’ voices seemed to lift me up and carry me. It was a transcendent, spiritual experience—hope, aspiration, determination, and teamwork all in one.”
Simon, you were our youngest climber to summit Kilimanjaro. How does it feel to tackle something so big at your age?
“I read a book in school called No Summit Out Of Sight, about Jordan Romero’s journey to climb the Seven Summits. It inspired me to climb Kilimanjaro and maybe more. If I’m being honest, I didn’t know I was CTSS’s youngest Kilimanjaro climber until after our trip. It was so amazing to be standing up there on the roof of Africa as a 12-year-old. I have been hiking my whole life, but never at high altitude.
Whenever I face a challenge now at home, I think of Kilimanjaro. If I can climb Kilimanjaro, I can push through and finish this. This was probably the most memorable thing I have done, and I can’t wait for the Mount Baker Alpine Academy next summer with CTSS.”
School is back in session, so we’re eager to know what you’ve told your friends about this experience. How do you describe what you achieved and learned?
“In Lexington, Kentucky, no kids really understand how difficult mountaineering is, nobody does it. When I got back to school, everyone was like “wow! You climbed Kilimanjaro”, and then forgot about it. One person actually congratulated me and made me feel really good about what I had done: my best friend, Aleksa. I called him every night before the climb, even though there was a seven-hour time difference. Anytime I got reception on the mountain, I tried to call him. My sixth-grade English teacher, Mrs. Hamby, had me read the book that inspired me, No Summit Out Of Sight. This year, I am going to be a guest speaker in her class when they are reading the book.”
Shared Summits, Shared Generations
Kristin and Simon’s journey to the Roof of Africa marked the start of a new kind of confidence, the kind that only comes from facing something vast together and emerging stronger on the other side. It reminded them that patience and trust sit at the heart of every challenge, on and off the mountain.
Their guide, Pega Sherpa, modeled that same quiet strength throughout the climb, steady, attentive, and deeply present. Guides like Pega embody what makes CTSS expeditions so unique: world-class skill paired with humility, heart, and genuine care for every climber’s journey.
For the Weeks-Sweeney family, that leadership turned an extraordinary adventure into a life-changing experience.
At CTSS, we believe mountains have the power to shape lives and strengthen relationships, one step and one shared summit at a time.
If you’re ready to start your own journey with a parent figure, or with a young person in your life, join us for a Rugged Luxury trek to Everest Base Camp, Kilimanjaro, or Machu Picchu, or for one of our introductory mountaineering courses on Mount Baker—where you just might bump into Kristin and Simon.
