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Who are Overland Leaders?

Overland leaders are bright, dynamic and accomplished college students and recent graduates from America’s best colleges and universities. Overland leaders 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 travel.

Far more than counselors, guides or instructors, Overland leaders are wonderful role models for our students, inspiring these young adults to understand the importance of friendship, consideration, teamwork and determination. Caring, motivated and fun, our staff of over 130 leaders ensures the safety and well-being of every Overland student.

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.). Last summer, more than 40 leaders returned to Overland for a second, third or fourth summer.

What Leadership Opportunities does Overland Offer? 

Outdoor, Service, Language and Writing Leaders:
Leaders of Overland's outdoor, service, language and writing programs have completed at least their sophomore year of college. We do our best to put together pairs whose strengths complement each other and whose personalities seem likely to work well together. 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 will occasionally have couples on staff but we will not place them together as leaders.

Support Staff:
Our dedicated support staff are the backbone of the entire Overland operation. Primary responsibilities include assisting with program logistics, especially at the start and end of each program, managing gear and providing office support for leaders in the field. Additionally, some support staff may be scheduled to lead a program as a part of their summer duties or provide hiking support for leaders in the field. Support staff fully participate in leader training. All support staff must have completed at least their first year of

“I am so impressed with the caliber of leaders chosen, and I feel honored to have been asked to lead for Overland.”   Victoria Thomas, Bates College ’08; Virgin Islands Service and Support ’08

What is it like to lead for Overland?

Challenge and Growth  
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. Overland offers summer hiking, bicycle touring, service, language study abroad and writing programs to young adults ages 11 to 18. Programs locations range from New England, Western US, Alaska, Hawaii, the Virgin Islands, Costa Rica and Europe.  Our focus on small, supportive groups and carefully crafted programs allow both students and leaders to have fun, develop close friendships, be challenged and grow through their experience.

 “From the moment you arrive at leader training you feel part of something completely amazing.”  Reid Berrien, Middlebury College ’08, Yellowstone Teton Explorer ’08; New England Explorer ‘07

Leader Training
Summer begins for all with ten days of leader training in Williamstown, Mass.  Through delicious meals, camping and leadership seminars, new leaders come to understand Overland traditions and culture from long- tenured directors and returning leaders.  Leader training also includes multi-day hiking or biking trips in the beautiful Berkshires. This training trip gives you an incredible opportunity to get to know your co-leader and focuses on creating a positive group dynamic.  During leader training, you and your co-leader will learn about the logistics of your program, the backgrounds of your students and the fundamentals of Overland's approach to leading students through a great summer.

“Leader training is a great way to start the summer.  Seminars, the backpacking trip, dessert circle, meals; all were amazing. The energy of returning leaders is infectious! “  Dan Golub, Williams College ’08; Language and Service Costa Rica.

Commitment to Overland
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 are again filled with delicious meals, laughter and friendship. Leader closing serves 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.

“I cannot even begin to list the numerous reasons why leading for Overland made me the adult I am today.” Anika Basu, Syracuse University ’10; Vermont Bike Trip ’08, Support, Summer Writing Program, Berkshire Adventure ’07 

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 make working for Overland such an amazing opportunity.

“My summer with Overland was the most fulfilling, fun, and inspiring summer of my life. I was surrounded by the friendliest, most hard-working and interesting people I have ever met.”  Annie Bigwood, Connecticut College ’11;  Support Staff, New England Adventure, Berkshire Adventure ’08

What do Past 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

Meet some of our spectacular returning leaders.