Expedition & Course Instructor

Join to apply for the Expedition & Challenge Course Instructor role at Chesapeake Bay Outward Bound School.

At Chesapeake Bay Outward Bound School (CBOBS), we believe every young person is capable of more than they know. Through immersive outdoor experiences, we help youth develop the courage, character, and leadership to thrive in school, in their communities, and for life. Located in Baltimore’s Leakin Park and our new location at THEARC in Ward 8 of Washington, DC, we serve thousands of students each year from diverse communities by facilitating powerful learning moments in nature.

As part of the Outward Bound USA network, we offer transformative experiences through backpacking, canoeing, Challenge Course, and team‑building that center on social‑emotional learning and equity‑driven education.

The Challenge Course Facilitator job is about much more than teaching youth how to climb. This work is about helping students discover more about who they are, what they’re capable of, and how they want to show up for others as teammates, leaders, and members of their community.

We’re hiring purpose‑driven, growth‑minded Challenge Course Facilitators for our Washington, DC team. You’ll lead 1‑day Challenge Course and team‑building programs, guiding students through purposeful activities, centered around predetermined outcomes, and guiding reflective discussions to drive transference of learning beyond our programming. You’ll help students build social‑emotional skills like teamwork and collaboration, perseverance and assertiveness, physical confidence and self‑regulation, social responsibility and self‑awareness.

If you thrive in a close staff community and are energized by coaching youth through real‑world learning, you’ll feel at home here. You’ll support students through physical, emotional, and social demands and help them turn new experiences into a sense of belonging, trust, self‑efficacy, and more.

Location:

Baltimore, MD

Full‑time, seasonal (Spring–Fall), includes multi‑day expeditions & 1‑day programs

March 23, 2026 & June 15, 2026

Per diem: $120.00 training; $144.00 after training

• Seven (7) days of Paid Sick Leave.
• Up to eight (8) weeks of paid Family/Medical leave.
• 401(k) with a match. Employees are eligible for participation after 6 months of employment. The current match is 3% of the employee’s salary.
• Pre‑tax Commuter/Transit Benefits.
• Employee Assistance Program (EAP).

• Room and basic Board, if you elect to live in CBOBS’ staff house.
• Access to Pro‑deals.
• Discounted rates for Staff Invitationals at other Outward Bound bases during the off‑season.

• Facilitate 1‑day and multi‑day courses (Challenge Course, backpacking, canoeing, sea kayaking, rock climbing and wilderness living) with a strong education focus - not just technical instruction.
• Design and adapt curriculum and session plans toward clear outcomes:
  Belonging, Courage, Physical Engagement, and Reflection. Craft daily progressions, reflection prompts, and debriefs to those outcomes, adjusting for student needs and partner goals.
• Assess student learning by using group feedback tools, facilitated debriefs, and end‑of‑day reflections to transfer course learning into take‑home skills and commitments.
• Coach students through tough moments by leading through humility, resilience, and openness - and helping them turn challenge into growth.
• Co‑lead with a partner instructor to manage group dynamics, logistics, and risk.
• Participate fully in onboarding, expedition prep, field support, and course debriefing.
• Uphold safety policies and procedures and contribute to an emotionally and physically safe course environment.

• 21+ years old.
• Must clear a federal and state background check.
• Adult CPR and First Aid, with Epi Pen training.
• Experience with youth (ages 12–18) in schools, mentoring, camps, or community programs.
• Comfort with camping, backpacking, or wilderness living (training provided).
• Commitment to equity, inclusion, and working with diverse populations.
• Able to work long, variable hours in high‑stress, team‑based, and…