A Message from the Directors:

Kevin & Birgitta Cashman, with Jack & Sam; Susan & Chad Olcott, with Phoebe & Liliana.

Welcome to Apogee’s 21st season! Since the beginning, we have passionately delivered fun, life-changing summer experiences to young people. In the summer of 2022, we will welcome more than 800 students to the Apogee family and run more than 75 adventure and service trips.

Accredited by the American Camp Association, our program continues to thrive because we know that top-notch leadership and a personal connection are both key to the success of our trips. Our trip leaders are, quite simply, the very best you will find. And at Apogee, we know each student by name and invest in them individually. Parents will feel welcome, too – we’re always available and excited to speak with you. This warm, family atmosphere is what we’re all about; it’s what allows Apogee students to flourish and parents to feel at ease.

If you’re already part of the Apogee family, we can’t wait to see you again. And if you’ve never spent a summer with us, we hope 2022 is the year you do!

Please join us!


Kevin Cashman, Founder/Director                       Chad Olcott, Director


Assistant Director Miles Bent was born and raised in Virginia’s beautiful Shenandoah Valley, hiking and exploring the Blue Ridge Mountains. A 2017 graduate of Washington and Lee University (W&L, for short), Miles studied Global Politics and English, played varsity soccer, and served as a peer counselor to incoming first-years at the college. Miles was first introduced to Apogee while at W&L, and went on to lead Maine Coast College Essay in 2015, Pacific Coast in 2017, Europe Coast to Coast in 2018, and Vermont to Montreal in 2021. Before joining Apogee’s full-time team in January of 2022, Miles spent his previous four years in Washington, DC, where he worked as a cybersecurity consultant, a bartender and as a Program Manager at a youth outdoor education non-profit. When he’s not at the office you can find him running with his dog, biking, hiking, snowboarding, reading, or playing board games with anyone who will put up with his competitiveness. Send Miles an email.


Assistant Director Claudia Bueermann was raised all over the country, most recently calling the Pacific Northwest her home. A graduate of Whitman College, Claudia (who also happily goes by “Clouds”) majored in Anthropology and Geology. Outside of her coursework at Whitman, Claudia mastered the art of outdoor trip logistics by working as a trip coordinator and leading rafting, backpacking, and cross-country skiing trips for the Outdoor Program. Claudia has since lent her talents to places beyond Whitman, working as a river guide in Idaho and Oregon and in the rich wine industry in Walla Walla, Washington. Most recently, Claudia worked for NOLS at their river base located in Vernal, Utah before joining the Apogee team full time in May of 2021. When not working, she is most likely out climbing, skiing, knitting, or picking up cool looking rocks saying “wait, but look at this one!” Send Claudia an email.



Founder and Director Kevin Cashman grew up in Westfield, NJ and attended Dickinson College. Since graduating from Dickinson in 1995, Kevin has worked almost exclusively in the outdoor adventure travel field. In 2001, after working for years as a trip leader and director for other outdoor programs, Kevin followed his dream and founded Apogee. His passion and perseverance for Apogee have paid off through the years and have resulted in a thriving, highly respected program. Having led the trips in Apogee’s early years, Kevin knows exactly what goes into crafting a successful adventure. One of his greatest satisfactions is making connections with Apogee students and their families. He has an uncanny ability to remember names and details about many of the thousands of students who have taken part in the program over time. In addition to loving his job, Kevin is an avid runner and loves to travel, especially by bicycle. Kevin is a Licensed Cycling Instructor with the American League of Bicyclists. He lives in Brunswick, Maine with his wife, Birgitta, and their two boys, Sam & Jack. Send Kevin an email.


Associate Director Shem Dixon was raised in the fresh air and among the mountain streams of western Maine. A 2011 graduate of Bowdoin College, Shem double-majored in Biology and Earth & Oceanographic Sciences. He also honed his leadership and communication skills as a Head Proctor in the College’s Residential Life program. With Apogee, Shem led our Coast to Quebec and Pacific Coast trips in the two summers after graduating from Bowdoin. He spent the intervening fall and spring seasons facilitating team-building for young adults at a Maine-based leadership development program. Shem re-joined the Apogee team as an Assistant Director in September 2013. Shem enjoys the challenges and rewards associated with coordinating logistics for more than fifty leaders, eighteen itineraries, and eight hundred students. Send Shem an email.



Associate Director Jack Messerly, a loyal Minnesotan, grew up fishing and playing pond hockey with his family near the Twin Cities. His passion for hiking and camping took-off during his time at Hamilton College, which included leading Hamilton’s Adirondack Adventure program and a semester in New Zealand. At Hamilton, Jack studied Math and Philosophy – his favorite course being “The Philosophy of Mathematics” – and when he wasn’t in class, he was rock climbing and co-captaining Hamilton’s Men’s Rugby team. After graduating in 2014, Jack lived and worked on a farm in northern California before returning for his fourth summer with Apogee, this time as a full time Assistant Director. He’s led four different Apogee trips since he began leading in 2012: New England Mountains & Coast, Maine’s Downeast Explorer, California Mountains & Coast, and Apogee’s inaugural Alps Explorer. Send Jack an email.


Director Chad Olcott grew up between the hills of Western Massachusetts and the palm trees of Miami, Florida before attending Bowdoin College in Apogee’s hometown of Brunswick, Maine. After four summers of leading and supporting outdoor adventure trips throughout the United States during and after college, Chad was hooked on the adventuring lifestyle. Nonetheless, he spent six years practicing law, first as a JAG with the U.S. Navy in San Diego, California and Sardinia, Italy, before joining a law firm in Portland, Maine. In 2009, the siren song of the outdoors and experiential education proved too much to ignore, and Chad was delighted to join Kevin at Apogee. He finds his current mission – furthering Apogee’s goals of instilling personal confidence, character, and community-mindedness in every student – to be the most fulfilling work he could imagine. Chad lives in Brunswick with his wife, Susan, and their twin daughters, Liliana and Phoebe. In addition to his work with Apogee, Chad sits on the board of directors at Paradox Sports, a non-profit dedicated to transforming lives and communities through adaptive climbing opportunities. Send Chad an email.


Assistant Director Hannah Reed grew up in Charleston, South Carolina, and is a 2021 graduate of Washington and Lee University. As a Cognitive and Behavioral Science major, she conducted her senior thesis research on the mental health benefits of outdoor activity. While at school, she spent most of her free time with the Outing Club, whether it was leading pre-orientation trips on the Appalachian Trail, belaying students on the alpine tower, or leading canoeing and hiking trips as part of the club’s Key Staff. Hannah has also spent much of her time outside of W&L in the outdoor industry as she has spent summers working as a paddling counselor in North Carolina and leading outdoor adventure trips for teenagers in New England. Hannah moved northward to join the Apogee team in January of 2022 and when she’s not at work you can find her hiking, playing her guitar, whitewater kayaking, and reading books about geology. Send Hannah an email.


Associate Director Will Robertson is a 2014 graduate of Hamilton College, and grew up in the city of St. Paul, Minnesota. He was a Music Composition major at Hamilton, and could often be found singing on campus – be it with his A Cappella group, “Duelly Noted,” or one of the three other choral ensembles with which he sang. Will spent three years in the Twin Cities after graduating, running his freelance music business, singing in a professional choir, and coaching high school track and Nordic skiing. He would put these jobs on hold in the summer in order to lead with Apogee, starting with our Caribbean Service trip in 2014, Northwest Explorer in 2015, and capping off his Apogee leading career with our Alps Explorer trip in 2016. Will joined the full-time Apogee team in the spring of 2017. Send Will an email.



Assistant Director Andi Schweers grew up in the cornfields of rural Illinois before setting off to seek mountains and adventure. After graduating from the University of Colorado – Boulder with a degree in Ecology and Evolutionary Biology in 2013, Andi spent time moving through careers in professional hockey, hospitality/coffee shop management, before settling in the outdoor industry. Before joining Apogee in the fall of 2021, Andi spent five years coaching competitive climbing and working as the manager of the Alaska Rock Gym in Anchorage. While in Alaska, Andi also spent time as an ice climbing guide with Exit Glacier, where she guided a number of our Alaska Mountains & Coast groups during their day on the glacier. When not at work, Andi spends most of her time climbing, skiing, and reading book after book. Send Andi an email.