Outdoor Educators work with residential school programs leading groups of students on base-camping trips and teach outdoor living, team building and ecology through facilitating a variety of lesson topics; natural history, sustainability, organic farming, and canoeing. Educators live with their students and school chaperone in small camping groups at shore-side campsites on Chewonki Neck or on Islands out in Hockomock Bay, sleeping in tents, cooking over open fires or camp stoves to facilitate positive learning experiences in nature. In addition to their job responsibilities by season, educators are expected to take initiative and be part of the greater community, to support the Chewonki Mission of promoting personal growth, natural history, and community development.

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