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

A Message from the Directors:

Welcome to Apogee’s 20th season! While a global pandemic was most certainly not on our list of ways to mark this special milestone in our program’s history, it has unexpectedly crystallized and reconfirmed our belief in the value of what we do. Now more than ever we all recognize the importance of community, friendship, and service, not to mention the incalculable benefits of life experienced outdoors, where minds expand, bodies thrive, and spirits soar. 

There are still a number of uncertainties as we plan for Apogee 2021, but one thing is absolutely certain – we are committed to responsibly fostering the experiences that have, year in and year out since 2001, opened up the world to our students, nurtured individual confidence, and created communities built on respect and compassion. We pledge to put the physical and emotional well-being of our students and staff at the forefront of every decision we make, and to be open and transparent with our Apogee families about what to expect in the coming year – a year that will require careful planning, but one that holds so much promise. 

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 2021 is the year you do!

Please join us!


Kevin Cashman, Founder/Director                       Chad Olcott, Director


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 young boys, Jack & Sam. Send Kevin 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 enjoys volunteering with the Brunswick-Topsham Land Trust. Send Chad 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 sixty leaders, twenty-two 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 an Assistant Director. He’s led seven Apogee trips since he began leading in 2012: New England Mountains & Coast, Maine’s Downeast Explorer, California Mountains & Coast (3 times), and Apogee’s inaugural Alps Explorer (twice). Send Jack 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.