Outward Bound Outdoor Educator

Chesapeake Bay Outward Bound School

Baltimore, Maryland

Job Type Permanent
Salary Details 10000-14000


As leaders in the wilderness based experiential education field, we look to hire staff that have a strong desire to educate youth. Our staff are mission-driven, creative, diverse, and inclusive. Our staff members come from varied backgrounds; they are traditional classroom educators, wilderness educators, outdoor enthusiasts, veterans and much more. They are folks who have sought out a work life that is inspiring, impactful, challenging and fun. 

The populations we work with are just as varied as our staff. The youth of Baltimore and DC make up the greatest segment of our student population. Field staff must have a strong will and desire to deliver our mission to those who could benefit most from it. We also serve students who come from all over the country, youth who have risen to leadership roles in their schools, on sports teams, and within other community organizations. We serve veterans, large corporations, kids as young as 10 and adults of all ages. 

Applicants who demonstrate professionalism, commitment, and interpersonal competence will be extremely successful. Outward Bound field staff are also flexible, humble, and open-minded leaders. They seek out opportunities for growth, can give and receive feedback and demonstrate effective communication skills. They display proven and sound judgment in challenging circumstances but also the ability to learn from mistakes. Our community and culture are centered around humility, self-awareness, sense of humor and compassion. 

We deliver our mission on High Ropes courses, backpacking on the Appalachian Trail, canoeing on the Potomac River, and kayaking the Chesapeake Bay. Applicants who have outdoor experience will be highly competitive. That said, a proven and sustained ability to work with underserved populations in an urban setting is of utmost importance. As you can imagine, individuals who encompass these skills are the most desirable candidates for field staff positions. 

Excellent candidates:  

  • Can meet our students where they are, adapting instruction to support learning styles and educational needs, as well as guide meaningful discussions, develop and organize lesson plans, and practice humility, humor, and compassion in their approach.  
  • Value relationships and practice effective self-care, individuals who can build rapport with students and staff from diverse backgrounds, have effective communication skills, and can give and receive honest feedback.    
  • Comfortable managing risk inherent to our programs includes understanding and supporting the social, psychological, and physical challenges for themselves, fellow staff, and all students.  


During the Spring and Fall seasons, we partner with nearby public, charter, and independent schools to deliver 5-day expeditions and 1-day programs. In the Summer, we welcome students from around the world on longer, 8- 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. Our day programs serve mostly school students during the Spring and Fall. Over the Summer, we work with groups from summer enrichment programs, camps, or mentorship groups. From mid-November to mid-March, our base shuts down for the Winter months; during this time, instructors often travel, find other work in education or the service industry, and/or pursue other interests in the Baltimore area.  

Chesapeake Bay Outward Bound School’s Baltimore base provides the best of both worlds. Located in the 1,216-acre Gwynns Falls Leakin Park in Baltimore, MD, the base is within city limits, with easy access to Baltimore City while still being in a huge, wooded park. Chesapeake Bay Outward Bound School is also actively developing its base in Washington, D.C., with offices located at the Josephine Butler Parks Center. Our D.C. partnerships are growing constantly, and we work directly with D.C. Parks and Recreation to revitalize several of D.C.’s green spaces. 


  • Must be 21 years of age or older.  
  • Ability to clear federal and state background checks.  
  • Have exposure to and comfort with backpacking, camping, and wilderness living.  
  • Must work well in a team environment and excel under pressure.  
  • Current Wilderness First Responder (WFR) certification preferred. Adult CPR and First Aid Certification required. 
  • Vaccinated for COVID-19 
  • Ability to work in a team environment and support CBOBS philosophy and mission. 


  • Actively engages in personal and professional growth, participating in mandatory and educational training opportunities.  
  • Engages in sharing and receiving clear, effective, and timely communication and feedback with their supervisors, co-instructors, and other staff members.  
  • Work effectively with students 12 - 18+ years in age, students who have never camped before, and students from marginalized communities.  
  • Be a positive role model for staff/board members/clients/students by maintaining an appropriate appearance, a positive attitude, and professional demeanor. 
  • Deliver the Outward-Bound mission and Education Framework while teaching course components and encouraging teamwork, cooperation, challenge, and service.  
  • Supports other instructors and program managers in all aspects of course safety; identifying, assessing, and managing environmental and social risks within their scope of experience.  
  • Adheres to all local operating procedures, safety policies and emergency procedures outlined in the staff manuals and employee personnel policies, procedures, and handbook 
  • Assists with logistical functions such as food packing, course transport, equipment resupply, gear maintenance, and facility support.  
  • Participate in the emergency response system as assigned, which may include driving, supporting evacuations, assisting in field support calls, or managing a student group in lead or instructor absence.  
  • Takes personal ownership to initiate, seek out, and commit to professional development through training and additional work experience.  


  • Basic knowledge of the Outward-Bound mission 
  • Demonstrates multicultural competence and awareness 
  • Demonstrates sustained ability to work with underserved populations  
  • Background in Coaching, Mentoring, Education, Physical Sciences, Social Sciences, Experiential Education, Non-Profit Management, or other related disciplines  
  • Effective communication skills  
  • Proficient with computers  
  • Organized, with an ability to prioritize time-sensitive assignments  
  • Creative and flexible 


The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job. Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions.  

  • Ability to carry 45–65-pound hiking pack on and off trail for 12 hours or more a day.  
  • Possesses mental stamina, adaptability, and emotional maturity to supervise students and support co-instructors in a wilderness, remote course environments 24/7.  
  • Be sufficiently fit to participate in all required activities, including but not limited to backpacking, climbing, paddling, ropes courses, rock climbing, running including ability to work in small spaces, at height, and to lift, crawl, bend, carry, push, and pull.  
  • Ability to maintain energy, strength, and focus to assist students and staff with physical and emotional challenges in complex situations.  
  • Ability to objectively assess staff and participant behavior, determine its appropriateness, enforce safety regulations and emergency procedures, and apply appropriate management techniques.  
  • Visual, auditory, and physical ability to identify and respond to hazards related to activity and emergencies and possess strength and endurance required to maintain constant supervision of staff.  
  • Capacity to care for personal needs (physical, mental, and emotional) in a high stress, sometimes unpredictable outdoor environment.  
  • Capability to work on feet most days, sometimes 16+ hours, with daily exposure to the sun, heat, and animals such as bugs, snakes, bats, bears, etc.  
  • Maintain a positive outlook and make clear, concise decisions regardless of changes in weather, schedules, and plans in a remote environment.  
  • Operate office equipment including computer, keyboard, calculator, copier machine, and other office equipment.  


  • Compensation: $90/day as a New Instructor in training. The training period usually lasts 16 weeks (about 3 and a half months). Promotion to Assistant Instructor is rolling, is expected in your first year, and is paid at $105/day. On average, a New Instructor who starts in March and works the full program year (through November) grosses about $10,000--$14,000 their first year. Opportunity for promotion ongoing. 
  • Outward Bound curriculum and facilitation trainings  
  • Outward Bound technical trainings  
  • Room and board  
  • Professional Development: 15-20 formal opportunities per contract year that promote technical and non-technical skill mastery 

Please apply via our website


When you apply, please indicate that you are responding to the posting on Conservation Job Board.

Category Environmental Education , Outdoor Recreation
Tags Trail Maintenance