Chesapeake Bay Outward Bound School is seeking experienced wilderness instructors to lead expeditions in the summer of 2021 and continue into the fall. This position requires extensive wilderness experience and the ability to safely and effectively manage risks in the backcountry. Instructors would engage in a variety of trainings to support their transition into a leadership role. Trainings may include backpacking, sea kayaking, canoeing, challenge course training, rock climbing, student management training, as well as shadowing other expeditions. In addition to managing the safety of expeditions, lead instructors are individuals who can mentor new instructors, meet desired educational outcomes, role model positive social and emotional skills, and deliver culturally relevant programming for a wide range of participants and socio-economic backgrounds. Instructors must be familiar with leadership models and understand how expeditionary learning can fit into the development of social and emotional skills for youth. During the spring and fall seasons, we partner with nearby public, charter, and independent schools to deliver 5-day peer leadership expeditions. In the summer, we welcome students meeting for the first time to go on longer 7 to 12-day expeditions. We backpack on the Appalachian Trail and in the Dolly Sods Wilderness, canoe on the Potomac River, and sea kayak on the Nanticoke River near the Chesapeake Bay. All expeditions are led by teams of 2 or 3 individuals, 1 of which is the lead instructor. We offer day programs as well, which mostly serve local schools in the shoulder seasons. This position offers on-going professional development opportunities, room and board, and the chance to connect with an incredibly strong and inspiring community of educators. Located in the 1,216 acre Gwynns Falls Leakin Park in Baltimore, MD, the Chesapeake Bay Outward Bound School provides the best of both worlds by being located within city limits, as well as a protected wilderness area. This is a full time seasonal position with advancement opportunities on a yearly basis.


Knowledge & Skills

  • Must have Wilderness First Responder certification
  • 1-2 years field experience
  • Basic knowledge of the Outward Bound mission
  • Demonstrates multicultural awareness and ability to engage a wide variety of student populations
  • Strong communication  and leadership skills
  • Strong organizational skills with an ability to prioritize time-sensitive tasks
  • Creative and flexible
  • Able to give and receive effective feedback that fosters positive professional development

Physical Requirements

  • 21 years or older
  • Complete a federal and state background investigation and a motor vehicle record screen
  • On feet most days, sometimes for long hours (e.g. extended wilderness expeditions and occasional support days that run from early morning to late evening)
  • Ability to carry, lift and move a minimum of 40 pounds

Essential Duties & Responsibilities

  • Participates in staff training and actively takes initiative in personal professional development
  • Delivers programs that foster students success by building a positive group culture and teaching teamwork and leadership skills
  • Being a positive role model and mentor for other staff
  • Manages and assists with field evacuations, student supervision and other various program tasks as needed
  • Manages logistical functions of expeditions, including gear pack, food pack, transport, and resupplies
  • Adheres to all local operating procedures, safety policies and emergency procedures outlined in the staff handbook

Compensation & Benefits

  • 5 month full time position with a guaranteed minimum stipend of $1600 per month. Per diem continuation of this position is expected to continue through the Fall.
  • Pay above $1600 built from per diem rate commensurate with experience and days worked
  • Exposure to Outward Bound curriculum and facilitation training
  • Exposure to Outward Bound technical training
  • Room and board
  • Professional Development: 15-20 formal opportunities per contract year that promote technical and non-technical skill mastery

How to Apply

Please submit resume and cover letter via email to Rice Ermilio, People & Culture Coordinator, at

Chesapeake Bay Outward Bound School prohibits discrimination against any student or applicant because of race, color, religion, sex, gender, ethnic or national origin, sexual orientation, qualified individuals with disabilities on the basis of disability, or any other category which may be protected by applicable state or federal law. Chesapeake Bay Outward Bound School also promotes respect for all people, and will not tolerate harassment based on any of these characteristics nor on differences based on gender identity or expression.