Spring: March - June
Summer: June - August
Fall: August -November


The Instructor Apprenticeship at Chesapeake Bay Outward Bound School is a 10-week program meant to prepare participants to become full-time Field Instructors at the end of their apprenticeship. During the 10-week program, apprentices perform essentially two types of work: shadowing and support. Through shadowing on both Day Programs and Expeditions, apprentices observe, try, and experience what makes an excellent Outward Bound program with the support of seasoned instructors. Apprentices also provide invaluable logistical support to the base. Through working logistical support, apprentices also gain an inside look at how our base operates and the work that goes into creating a successful program. Both program shadowing and logistical support work provide apprentices with experiences and knowledge that will serve them immensely as instructors. Because the organization invests so much in the development of apprentices, we ask that applicants have both interest and ability to instruct at Chesapeake Bay Outward Bound School for at least one year, but preferably more, after their apprenticeship.

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 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. Similarly, our day programs serve mostly school students during the spring and fall. Over the summer, groups of summer enrichment programs, camps, or mentorship groups. Each week throughout the year, we 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 pursue other interests. A few stick around base to work the PYC program each week.

Located in the 1,216 acre Gwynns Falls Leakin Park in Baltimore, MD, Chesapeake Bay Outward Bound School provides the best of both worlds. The base is within city limits, with easy access to Baltimore, while still being in a huge, wooded park.

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


Outward Bound Apprenticeship: What to Expect

Instructor Jake Wills gives insight on the experience.  "Fulfilling. Energetic. Immersive. Growth. Current instructors chose these words to describe their Outward Bound Apprenticeship. Many instructors consider this position to have been an exceptionally influential time in their lives. The focus on self-development, experiential learning, and community sets the tone for your tenure at Outward Bound."
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Knowledge & Skills

  • 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 discipline
  • Strong communication skills
  • Proficient with computers
  • Organized, with an ability to prioritize time-sensitive assignments
  • Creative and flexible

Physical Requirements

  • 21 years or older
  • Complete 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.

Essential Duties & Responsibilities

  • 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
  • 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

Secondary Duties & Responsibilities

  • Takes personal ownership to initiate, seek out, and commit to professional development through training and additional work experience
  • Other duties as assigned

Compensation & Benefits

  • Exposure to Outward Bound curriculum and facilitation training
  • Exposure to Outward Bound technical training
  • 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.

How to Apply


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

Baltimore 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. Baltimore 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.