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What does Overland offer?

Overland offers hiking, bicycle touring, service, language study abroad and writing programs to young adults ages 11 to 18. Our focus on small, supportive groups, carefully crafted adventures, and inspiring leadership allows both students and leaders to have fun, develop close friendships, be challenged and grow through their experience.

Why lead for Overland?

When we ask our leaders for just one reason to spend the summer with Overland, we get a variety of answers. Spending time with kids. Having fun. Being challenged. Working with inspiring peers. Exploring the world. Serving as a role model. Being part of a spirited community. Developing strong friendships. Making a difference. All Overland leaders agree, however, that it is the unique combination of all of these reasons that makes working for Overland such an amazing opportunity.

Who are Overland's Leaders?

Overland's leaders are bright, dynamic and accomplished college students and recent graduates who are motivated by the desire to have an impact on the lives of the students they lead, while enjoying the camaraderie of inspiring colleagues and the excitement of world travel. Caring, motivated and fun, our staff of over 100 leaders ensures the safety and well-being of every Overland student. Far more than counselors, guides or instructors, Overland's leaders are wonderful role models for our students, inspiring these young adults to understand the importance of friendship, consideration, teamwork and determination.

Our staff ranges in age from 20 to 27, with most leaders between the ages of 21 and 24. Most of our leaders have completed at least their sophomore year of college, worked with kids and had extensive leadership experience--typically through high school and college leadership positions (e.g., sports teams, student government, outing club, service organizations, language clubs, etc.).

Meet some of our spectacular returning leaders.

What is it like to lead for Overland?

Leading an Overland program is one of the most challenging jobs you can imagine, but it's also one of the most fun and fulfilling. You'll begin with a week of leader training. During these days you and your co-leader will learn about the logistics of your program, the backgrounds of your students and the basics of Overland's approach to leading. Once your program starts and your students arrive, you'll find that your days are exciting, fulfilling and fun--and that they are long, tiring and demanding: you will lead 24-hours-a-day, 7-days-a-week on programs that last from one to six weeks. At the end of your program, you will return to Williamstown for a few days to reflect on your experience, your students and your program's logistics. These days serve as a fitting end to your Overland summer as you reconnect with the rest of the staff and share stories from your travels and adventures around the world.

What do Overland leaders have to say about leading for Overland?

“Overland taught me to lead through inspiration. As leaders, Jack and I encouraged our students’ participation, guided their decision-making and imparted knowledge and respect for wilderness travel. But as leaders we also felt we should support their efforts to become leaders themselves. Jack and I worked to build groups that aspired to take responsibility for their own Overland experience.”

Bridget Igoe, Northwestern University ’03

At Overland, I met the most inspiring people I have ever encountered. I was re-energized each summer by my co-leaders, by how hard they were willing to work and how much they were willing to give. I was constantly amazed and motivated by how much faith the staff had in us, and the last thing I was going to do was let them down. Because of Overland, I am confident in my leadership abilities.

Molly O’Connor, Amherst College ’03

Overland taught me that a great leader never gives up; the group is relying on him to persevere and succeed. When others put their faith in me to do something, I know that I cannot and will not let them down.”

Robbie Cowden, Dartmouth College ’06

Overland shows its leaders and students alike the tremendous potential of a single day. Overland trips are essentially experiments in possibility; leaders and students emerge from the summer with the understanding that they can do anything. Really: anything. This changed my life, and I know it has changed the lives of many of the students that I have led.

Elizabeth Turnbull, Colby College ’04

What types of positions are available at Overland?

Outdoor, Service, Writing & Language Leaders

Leaders of Overland's outdoor, service, language and writing programs have completed at least their sophomore year of college. Leaders work in coed pairs. We do not have a senior leader and a junior leader; our leaders are equals who strive to create a family-like environment within the group. We do our best to put together pairs whose strengths complement each other and whose personalities seem likely to work well together. We will occasionally have couples on staff but we will not place them together as leaders.

Support Staff

Our hard working support staff makes up the backbone of the entire Overland operation. Primary responsibilities include assisting with program logistics, especially at the start and end of each program, tuning bikes, managing gear and providing office support for leaders in the field. Additionally some support staff may be scheduled to lead a bicycling trip as a part of their summer duties or provide hiking support for leaders in the field. All support staff must have completed at least their first year of college.