The 16-week probationary period lets new instructors assess their readiness for the role of full-time instructors, as well as allowing Chesapeake Bay Outward Bound School (CBOBS) to determine their ability to meet all job requirements. Upon satisfactory completion of the training period, you may be offered a position as either a per diem or full-time… READ MORE >

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… READ MORE >

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… READ MORE >

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.

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.

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… READ MORE >

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… READ MORE >

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.

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… READ MORE >

Yes, we are here to chat.  We encourage you to send inquiries about the position to jobs@outwardboundchesapeake.org. We look forward to connecting!