Chelsea Colby

During my time at Middlebury College, I fell in love with the community in Addison County, Vermont. After graduating, I began my teaching career at a local elementary school where I was the school’s beekeeper and loved taking my students out snowshoeing and Nordic skiing. During winter weekends, I taught alpine skiing to students of all ages at the Middlebury College Snow Bowl. As a teacher, I spent my summers seeking adventures throughout New England including thru hiking the Vermont Long Trail and the New Hampshire Cohos Trail. In subsequent summers, I was looking for a way to bring my passions together and Overland was the perfect match – teamwork, discovery, and sustainability. In the summer of 2022, I had the incredible opportunity to lead Rocky Mountain Expedition and in 2023 I returned to lead Service and Hiking Alaska.

As a teacher and a leader, I love to experience the intense and wonderful power of immersive outdoor experiences and the ways they invite us to grow as individuals and bring us together in community. I’m thrilled to join the Overland year-round team where I can develop relationships with families and cultivate these inspiring and empowering experiences for students.