Work That Changes Lives - Empower students, explore nature, and grow as an educator and leader.

Location: Baltimore, MD
Schedule: Full-time, seasonal (Spring–Fall), includes multi-day expeditions & 1-day programs
Start Dates: March 23, 2026 & June 15, 2026

Compensation and Benefits: 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).

Other Perks:

• Room and basic Board, if you elect to live in CBOBS’ staff house

• Access to Pro-deals

ABOUT US

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 expanding into Washington, DC, we serve thousands of students each year of all ages, backgrounds, and socioeconomic status by facilitating powerful learning moments in nature. As part of the Outward Bound USA network, we offer transformative experiences through backpacking, canoeing, sea kayaking, rock climbing, Challenge Course, and team-building that center on social-emotional learning and equity-driven education.

This is not a job about teaching outdoor skills for their own sake. This is about helping students discover who they are, what they’re capable of, and how they want to lead.

WHAT WE’RE LOOKING FOR

We’re seeking purpose-driven, growth-oriented Field Instructors to lead multi-day expeditions and 1-day Challenge Course programs for our Baltimore team. You’re an educator first, using the outdoors as your classroom to plan, facilitate, and assess learning that builds confidence, teamwork, and empathy. 

Full-time Instructors are cross-trained and expected to lead both Day Programs and Expeditions. Most students will be new to the outdoors; you’ll meet them where they are and guide incremental growth through intentional challenge.

WHAT YOU’LL DO

• 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.

WHAT YOU’LL BRING

Minimum Qualifications

• 21+ years old

• Must clear a federal and state background check

• Adult CPR and First Aid, with EpiPen 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 outdoor environments for single-day and multi-day experiences

• Ability to carry a 45–65 lb pack, hike 5-15 miles a day in uneven terrain, supervise students 24/7 on expedition, and remain emotionally regulated under pressure.

• Valid driver’s license with insurable driving record (preferred, not required).

WHAT SUCCESS LOOKS LIKE

• Students report a stronger sense of self-confidence, trust, and teamwork because of their Outward Bound experience

• You build meaningful, trust-based relationships with students and peers
  You demonstrate resilience, flexibility, and reflection, modeling calm, reflection, and follow-through

• You commit to and complete at least one full season (March–November or June-November preferred)

• You grow as a facilitator, teammate, and changemaker

For full details on training, expectations, and onboarding, review the detailed Candidate Infosheet here.

WHAT MAKES THIS ROLE EXCITING

This is not just a job - it’s a journey of personal transformation, just like the ones you’ll lead students through. You’ll:

• Make real-time impact: Enable students to build courage, empathy, and self-trust, one challenge at a time.

• Grow alongside others: Join a tight-knit, passionate community that values learning, feedback, and purpose.

• Gain professional tools: Facilitation, trauma-informed care, group management, risk management and emotional intelligence - all transferable to future careers in education, counseling, or social impact.

• Step into purposeful growth:  If you enjoy pushing yourself to the edge of your boundaries - emotionally, physically, and professionally - and believe people grow through challenges, you’ll feel at home here.

This work can include extended field weeks and quick turnarounds. We design experiences to be demanding for growth, and we prepare you to lead them well - with training, mentoring, clear safety systems, and a supportive team. Our aim is to set honest expectations, provide the tools to succeed, and recognize your impact.

DIVERSITY, EQUITY, AND BELONGING AT CBOBS

Chesapeake Bay Outward Bound School serves students across the DMV - Baltimore, Washington, D.C., and communities throughout Maryland and Northern Virginia - and welcomes young people from around the world in the summer. We believe every student deserves access to safe, challenging, and joyful outdoor learning close to home.

We’re building a team that reflects the populations of the communities we serve. We welcome candidates of all backgrounds, identities, and lived experiences, including multilingual staff and educators with deep ties to Baltimore and D.C. communities. If you share our commitment to equity, inclusion, and belonging - and to helping students grow courage, confidence, and empathy - we’d love to hear from you.

ADA & Reasonable Accommodation

CBOBS provides equal employment opportunity and will consider reasonable accommodations for qualified applicants and employees. If you need an accommodation for the application or interview process, or to perform the essential duties of this role, please contact jobs@outwardboundchesapeake.org. Requests are reviewed on a case-by-case basis consistent with the ADA and applicable law. 

Essential functions (with or without reasonable accommodation) include hiking on uneven terrain, carrying 45–65 lb packs, supervising students overnight, and working outdoors in varied weather.