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 a protected wilderness area. This is a full-time seasonal position.

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

Compensation & Benefits:
Room and board
Professional Development: 15-20 formal opportunities per contract year that promote technical and non-technical skill mastery.
Employee Assistance Program (includes counseling and financial coaching)
Instructor Pay Range: Lead Instructor Level 1: $105/day, Lead Instructor Level 2: $120/day, Lead Instructor Level 3: $135/day

Tagged as: Backcountry Skills, Climbing Skills, Instruction and Guiding, Teaching/Education, Therapeutic Counselors, Water Skills


Wilderness First Responder
21 years or older
1-2 years field experience

Required Skills:

Basic knowledge of the Outward Bound mission
Demonstrates multicultural competence and awareness
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
Able to mentor and coaching new instructors

About Chesapeake Bay Outward Bound School

The Chesapeake Bay Outward Bound School is part of an international education movement dedicated to the idea that people are capable of far more than they know. Our leadership programs and character curriculum empower individuals in local schools, community organizations, and the police department to effect positive change in Baltimore and Washington D.C.

Application Instructions

Please send all applications to Joey Barness at [email protected]