Spring Start: March - June Training
Summer Start: July - October Training


New instructors at Chesapeake Bay Outward Bound School start their employment with a rigorous, training-heavy 16-week period meant to prepare them to become full-time instructors at or before the end of the 16-week period. New instructors will spend the first phase of this period in formal trainings designed to introduce instructors to what it means to work with students, how to manage risk in our course areas, and how to create the outcomes-oriented student experience we strive for. In the second phase, new instructors will begin to engage with our work! New instructors will work primarily in support roles and as co-instructors on programs. Through working in the support role, new instructors gain an inside-look at how our base operates and the work that goes into creating a successful program. While co-instructing on both Day Programs and Expeditions, they will observe and experience what makes an excellent Outward Bound program and apply their training, all with the support of experienced lead instructors. Both program support work and co-instructing provide new instructors with experience and knowledge that will be formative for their career as an instructor. 

A Year at CBOBS

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 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. Similarly, 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. Throughout the year we also run the Police Youth Challenge – a program designed to bring students from Baltimore and Baltimore Police Officers together for a day of building trust and breaking down bias. 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 a 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 in an effort to revitalize several of D.C.’s green spaces. 

If you are motivated to serve young people and be a part of a supportive, fun, and hard-working community, apply to be an Instructor today! 




  • 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 
  • Strong communication skills 
  • 21 years or older 
  • Pass 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 
  • Must have all vaccines recommended by the CDC, including a COVID 19 vaccine 
  • Should be comfortable in the outdoors and able to responsibly care for personal needs in outdoor environments
  • Participates in staff training as appropriate 
  • Works towards clear, effective, and timely communication and feedback with their supervisors, instructors, and other staff members 
  • Helps Outward Bound staff and students succeed by encouraging teamwork, cooperation, and individual effort 
  • Is a positive role model for staff/board members/clients/students by maintaining an appropriate appearance, a positive attitude, and professional demeanor 
  • Is growth-oriented and works towards a deep understanding of Outward Bound programming with the goal of being able to mentor other new instructors 
  • Assists with field evacuations, student supervision, and other various program tasks as needed 
  • Assists with logistical functions such as food packing, course transports, equipment resupply, gear repair and cleaning 
  • Performs base site tasks as assigned, such as building and maintenance of program facilities, sites and equipment 
  • Assists with administrative functions such as development of marketing materials, school briefings, event planning, and data entry 
  • Adheres to all local operating procedures, safety policies and emergency procedures outlined in the staff handbook 
  • Takes personal ownership to initiate, seek out, and commit to professional development through training and additional work experience 
  • Other duties as assigned
  • Outward Bound curriculum and facilitation trainings 
  • Outward Bound technical trainings 
  • Room and board 
  • Monthly stipend of $1,500 
  • Professional Development: 15-20 formal opportunities per contract year that promote technical and non-technical skill mastery
What is the schedule like?
During training, you will be doing all sorts of different work to get you a taste of everything we do. You can expect to work approximately 18—23 days a month during this time, and you’ll be notified of your expedition programs well in advance. Once you transition to per diem employment, you will be given a work agreement at the beginning of each season that outlines your expedition programs. During and after training, you will receive your schedule through the When I Work scheduling app. For single day work, you can expect your schedule to be final at 2 weeks out. 
What is a typical day like?
There aren’t many “typical” days as an OB instructor; it all depends on what kind of work you are doing that day! You might be in the backcountry on an expedition or facilitating a day program on our high- and low-ropes course at base. When you’re not directly instructing, you might be supporting our logistics team with putting away gear or driving an expedition crew back to base on their last day of expedition. You will get to experience all the work CBOBS has to offer in training after you start! 
What is your hiring process?
While we are accepting applications year-round, we have two main starting periods for incoming instructors. One in mid-March, and one in mid-July. Both start dates kick off an extensive instructor training period including field training, logistics training, and educational effectiveness workshops.
What trainings are available to instructors?
While we value hiring people with youth and/or outdoor experience, we train to meet excellent industry standards in education and wilderness management. We offer instructors training in Risk and Safety Management, Technical Outdoor Skills, Facilitation Skills, and Student Support Skills.
What is the position and pay like after the initial training period is complete?
During training, instructors are paid a training stipend of $1500 a month. Upon completion, instructors will move into per diem employment (meaning you are paid “per day,” as opposed to hourly or salaried employment) with a daily rate ranging from $105-120 depending on competency and program type. Once instructors have a proficiency in all aspects of CBOBS programming they are encouraged to apply to the Full Time Exempt (FTE) role, which is a salaried and benefitted role starting at $20,000 per year. As a perk of employment, CBOBS offers all instructors in training and any instructor who works in a student-facing part time capacity, room and basic board. 
What populations does CBOBS work with?
We work with a diverse population of people and students of all ages, 11 through adult. The majority of our programming however is with teenage and college-aged students across the Baltimore and Washington, DC regions. Throughout the spring and fall, we regularly partner with a range of Public, Charter, and Private schools and students 7th grade through 12 grade to run both day programs and multi-day expeditions.  
Can I work part-time?
Yes, once you have finished training. We consider part-time work to be an average of 10—15 days per month, and we have similar minimum work requirements for living in our staff house.
What does room and board look like?
Shared community housing is available for the duration of your time instructing with CBOBS. The recently remodeled historic mansion is located at our Baltimore base, with shared bunk rooms, community kitchen, laundry, library and porch. The Leakin Park location is one of the largest city parks in the country with plenty of hiking trails within your own backyard.  Food staples are provided and personal food that is labeled is welcomed. 
I have some questions about the application process. Is there someone I can talk to?
Yes, we are here to chat.  We encourage you to send inquiries about the position to our Culture and Communication Coordinator at


You may also submit your resume and cover letter to Patrice Ermilio at:

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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.

At The Chesapeake Bay Outward Bound School we believe that the most successful communities are made up of many perspectives and lived experiences. We want to hear your story and give you an opportunity to lead. We hope to eliminate systemic barriers to entry through the following hiring strategies. Learn more about our staff hiring practices.