A Personal Touch

Teamwork & Leadership

Summer biking trips take lots of preparation.

After six summers as an Overland student and leader, I joined Overland’s Operations team. Operations joins forces with the year-round staff in Williamstown to make sure every summer runs smoothly. In my time with Operations, I managed thousands of pieces of gear, shuttled dozens of leaders to airports, joined countless New England-based trips for hikes and pizza parties, and woke up bright and early for both long days at Leader Training and exciting trip start afternoons. 

Of all the work I did with Operations, however, one thing stands out: bikes. Overland has over 200 bikes that are used by students and leaders all over the country for our summer biking trips. Between trips (and over the winter), these bikes are carefully tuned to ensure that they’re in tip-top shape before they return to service. (These bikes live long, sustainable lives: after three summers with Overland, they’re sold to members of the Overland and Williamstown communities. I have one, as do my mother and sister!) 

A few weeks before Leader Training, the Operations team and I arrived in Williamstown to get to work making sure every bike was set to go for that summer’s students. Although there were hundreds of bikes for us to work on, it was a surprisingly personal process. As we started tuning each bike, we identified which student would ride it and which trip it would eventually go on. Olivia in Nova Scotia, Dan on Cape Cod, Emily in Vermont: as I saw the names and trips, my focus was not only on mechanics and components but also on the teen summer adventures and experiences that those bikes would provide Overland students.

Summer Biking Trip leaders

This personal touch is at the core of the Overland preparation process. The admissions team gets to know each and every student as they place them in a carefully crafted group. Leaders learn students’ names and a bit about them before they’ve even arrived at trip start. And those of us on the Operations team have the students in mind as we contribute to the countless hours of preparation that lead up to each student’s arrival. 

Editor’s Note: It is remarkable to see the effort and care put into each piece of preparation for these trips – whether it’s planning out meals, learning student names and hometowns, or making sure a bike rides just right. Operations staff like Owen do an incredible job of facilitating a smooth transition for our leaders and our students, so they can focus on being present with the group. See the summer biking trips Owen mentioned above here.


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