Instructor Apprentice
Chesapeake Bay Outward Bound

Instructor Apprenticeship! Opportunity to develop into lead expeditionary instructor

CBOBS base is tucked away in beautiful Leakin Park, just a car ride away from the inner harbor


Instructor Apprentice

Chesapeake Bay Outward Bound
Baltimore, Maryland
No experience required
Start Date:
Starts in about 2 months. (Aug 23, 2021)

The Instructor Apprenticeship at Baltimore 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 Baltimore 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.

How to Apply

Send a cover letter and resume to


Contact Info