Join Our Team


Current Job Openings

Recruiting Fair Schedule: Come See Us!

2022 Recruitment Schedule


  • February 24, 2022 - UMES (Virtual) 11am - 2pm
  • February 26, 2022 - Area Education Fair  (Teachers, Teacher Assistants, Paraprofessionals, Bus Drivers, Food Service Workers) 9am -1pm
  • March 14, 2022 - Kutztown University of Pennsylvania (Educators) 10am - 2pm
  • March 15, 2022 - Delaware State University 11am-4:30 pm
  • March 18, 2022 - Bloomsburg Education Fair (Education and Teacher) 1pm - 3pm
  • March 23, 2022 - Pittsburg Education Recruitment Consortium (Virtual) (Education) 12pm - 5pm
  • March 31, 2022 - SU/UMES Education Fair (Education) 11am - 2pm
  • April 1, 2022 - Towson Mega Career Fair 11am - 2pm
  • April 4, 2022 - University of Delaware Education Fair (Education) 4pm - 530pm
  • April 7, 2022 - Morgan State (Virtual  (Community Health, Education) 1pm - 4pm
  • April 11, 2022 - Penn State Education Fair (Education) 9am- 2pm

join our team!

Caroline County – You Belong Here!

Caroline County is a rural community known for its welcoming and collaborative culture. Our teachers are well respected within the community, and there is tremendous support for our public school system. There are many reasons why you belong here!

  • Outstanding school system with an excellent reputation
  • Competitive salary and benefits package
  • Student achievement in Caroline has been recognized as one of the best in the state
  • Class size averages are reasonable
  • Technology in Caroline is recognized as one of the most advanced in the state
  • Location is ideal: rural but within easy driving distance to Washington, D.C., Baltimore, Dover, Annapolis, and the Maryland and Delaware beaches
  • Cost of living is low compared to more urban areas
  • Low incidence of crime
  • A smaller school system is able to give its employees more individual attention
  • Rich and comprehensive program of staff development, including a supportive new teacher mentoring program
  • Strong foundation of community support

About CCPS

Caroline County Public Schools is a rural district in the heart of Maryland’s Eastern Shore. Learn more about our district by exploring the About Us, Leadership, and How We Teach pages on our website.


CCPS has more than 5,500 students and over 500 professional staff members with 10 schools located in a rural county on Maryland’s Eastern Shore.


CCPS has five elementary schools (Pre-K – grade 5), two middle schools (grades 6-8), two high school (grades 9-12), and one countywide career and technology center. Special education offers a continuum of services for all students with disabilities, including a preschool program. Visit each school's website (under Schools on the menu tab) for details.

Teaching Advantages

The Caroline County Board of Education has a long-standing commitment to maintaining desirable class size. A continuous building program serves to keep our schools’ maintenance and construction needs up-to-date.


Our school system prides itself on the use of technology in the classroom, both by staff and students. We offer many innovative opportunities for students to practice digital citizenship, communication, collaboration, creativity, and critical thinking skills using a variety of technologies.

recruitment incentives

  • Early decision bonus
  • Classroom supplies $200
  • Critical Needs Stipend (must be eligible for standard certification in Maryland and offered employment in the following areas: World Languages, Mathematics, Science, Special Education, and Technology Education)
  • Relocation Reimbursement
    • Up to 100 miles – up to $300
    • More than 100 miles – up to $1000

new teacher support

New Teacher Orientation

Teachers new to the county report four days before regular staff to become acquainted with their school, the school system, and the community.

Mentor Teacher Program

Each new teacher is assigned a mentor to assist with becoming acclimated to the school and instructional program. Teachers enjoy the benefits of a mentor for the first three years of teaching at CCPS.

New Teacher Seminars

A series of seminars are provided for new teachers. Seminars are designed to support teachers by extending their learning as well as providing opportunities for collaboration with others new to CCPS. The content of these sessions is dictated by the needs of the teachers.

New Teacher Newsletter

Every other month, CCPS publishes a newsletter designed to inform and assist new teachers in their first year of instruction.

New Teacher Handbook

Every new teacher receives a copy of The New Teacher Handbook which contains information about the school system and the county.


Deborah Siachos
Supervisor of Human Resources
410.479.2894 | [email protected]

Penny Bradley
Personnel Coordinator
410.479.2894 x1133 | [email protected]

Bridget Pennington
Human Resources Specialist
410.479.2894 x1128 | [email protected]