Leader Profiles: Josh Cutler, Laura Armstrong, Sam Tripp, & Ally Bolger

Without further ado, it’s time to dedicate this blog space to the four fearless leaders guiding our America Coast to Coast bike tours this summer. At more than 2700 miles – every single inch between the rising sun over the Atlantic near Charleston, South Carolina, and the Pacific’s setting sun at San Diego, California – this epic trip attracts the very best of the best in students and leaders alike.  We’re thrilled and proud that Josh Cutler and Laura Armstrong (ACC1), and Sam Tripp and Ally Bolger (ACC2) have heeded the call this summer. Read about our superstars here:

JOSH CUTLERApogee Adventures Leader Josh Cutler

He grew up in Uganda and Eritrea, he calls the shores of Lake Geneva home, he attended high school in Wales, is fluent in three languages, and he studies at the University of British Columbia.  Josh Cutler is our international man of mystery.  We are honored to have Josh return to Apogee for a fourth summer to lead our America Coast to Coast trip. In 2011 and 2012, Josh and his students had absolutely incredible adventures as he led our Maine’s Downeast Explorer, Northwest Explorer and Montana Service Adventure trips. Last summer, Josh returned to support our America Coast to Coast trip as they rode some of the hottest (and toughest) terrain in the country. Probably the only person you’ve ever met who has actually been chased by a hippo, Josh is remarkably down to earth.   An avid sailor and adventurer, Josh has taught safe-boating in South Africa, served as a camp-counselor in Italy, trekked through New Zealand, practiced wilderness rescues in Arizona, and worked in an orphanage in the Sudan.   At school, Josh has taken leadership positions with Greenpeace, a boat-building club, and Amnesty International.   The oldest of four boys, Josh takes every opportunity he can to work with young people.  He can’t wait to get back on his bike this summer with Apogee, and his cross-country students are sure to benefit from Josh’s outstanding leadership, his compassion and his truly global perspective.

Apogee Adventures Leader Laura ArmstrongLAURA ARMSTRONG

Apogee is thrilled to have returning leader Laura Armstrong back with us this summer! A 2012 graduate of Bowdoin College, Laura has a long history with Apogee: she was a student in 2004 and 2005 on our Cape Cod & the Islands and Montana Service Adventure trips, and in 2011, Laura joined Apogee’s leader ranks.  She led Apogee’s Coast to Quebec and Tuscan Service Adventure trips in the summers of 2011 and 2012, respectively. Last summer, she taught English in Costa Rica on a Fulbright Fellowship. Since returning last December, she has been teaching 11th grade social studies in Portland, Maine. At Bowdoin, Laura majored in History, with a concentration in Latin American Studies. Her semester abroad in Chile cemented her love for Latin American culture, doubtless feeding her interest in traveling to Costa Rica. Laura’s warmth and enthusiasm are evident to everyone that meets her, and her Apogee students will love her wonderful perspective on life and her interest in the wide world.

SAM TRIPPApogee Adventure Leader Sam Trip

We just can’t get enough of Sam Tripp at Apogee! Sam is a long-time Apogee veteran; he went on his first Apogee trip in 2007 on Coast to Quebec, and came back the next two years on our Montana Service Adventure and (the inaugural) America Coast to Coast trips. Sam returned to Apogee in 2012 as support staff, and will be an incredible addition this summer as he leads his students on our America Coast to Coast trip! Sam is from Rutland, Massachusetts where he grew up living and assisting his parents on their working farm. Sam’s passions lie in academics, the outdoors, and travel. Sam has been to many places around the world including British Columbia, Kenya, and Ireland. Sam graduated from Williams College in 2014.  At Williams, Sam studied Math and Economics. Sam completed his Senior Thesis this year on algebraic number series (already way above our heads), and has also been making time to spend outside. He recently has been involved with a program called Outdoor Outreach, where Sam and other college-aged leaders took elementary and middle school students hiking, rock climbing, and canoeing. Sam is looking forward to his second cross-country ride – this time as an Apogee leader. His students are going to love his hilarious personality, his passion for cycling, and, of course, his crazy math skills!

Apogee Adventures Leader Ally Bolger


After spending the summer of 2012 working with Apogee as support staff and 2013 leading our Pacific Coast trip, we can’t wait to send Ally Bolger out to lead our America Coast to Coast trip!  Ally is a New Jersey native with a serious passion for the outdoors.  She was a mere babe of eighteen months when her family took her on her first camping trip, a month-long road trip across several states.  It was on this trip that Ally’s impressive 44-state visit tally began, and since that first camping trip, Ally has traveled with her family all over the country, stopping to hike, kayak, and camp in National Parks on every journey.  Her outdoorsy and adventurous upbringing fostered hobbies like alpine and Nordic skiing, hiking, backpacking, kayaking, scuba diving, swimming, and, of course, cycling. Ally graduated from Colby College in 2013, where she studied Russian and Geology.  At Colby, Ally was an officer in the Outdoor Club and rowed on Colby’s varsity crew team.  During a semester abroad in Nepal, Ally completed a two-week backpacking trek through the “Khumbu” – the stunning region surrounding Mount Everest.  Ally has led pre-orientation backpacking trips for incoming freshmen at Colby, and worked as a camp counselor near her home in New Jersey. Last fall, Ally and her twin sister cycled through Europe, and then spent the winter working on a local ski mountain before joining the staff of an environment education school in Maine this spring. She can’t wait to combine her love for kids with her passion for the outdoors as she leads her Apogee students across the United States.

Apogee Leaders Ally and Sam

The dynamic-duo in 2012 – We can hardly wait to see more!