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What's Special About Us?

Our Family

The Caroline Family is comprised of a strong teaching, support, and administrative staff and a diverse group of students and their families.

Our Community

  • Caroline schools are at the heart of our towns and county.

  • We are the largest employer in the county.

  • We enjoy collaborative partnerships with local businesses, agencies, and county and town governments.

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Support for New Teachers

  • New teacher orientation in August

  • Seminar series throughout the year

  • Three year mentoring program

  • Robust professional development for all teachers throughout the year

Employee Benefits

  • Starting salary $50,000+

  • By 2026, starting salary increases to $60,000

  • High quality, comprehensive health insurance

  • Holistic employee assistance program

  • Opportunity for tax sheltered annuity

  • Nine credits of tuition reimbursement per year towards a Master's degree

  • Generous retirement benefits

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Location and Size

We enjoy our small town, rural lifestyle! We also love being a short drive from the beaches and city life in historic Annapolis, Baltimore and Washington, D.C.

We have a family-like atmosphere in each school and the district as a whole. School board members, the superintendent and district administrators are friendly, families faces.

Safety, Health & Wellness

  • A School Resource Officer is a full time member of each school family.

  • All schools have buzz-in entries, multiple surveillance cameras, and visitor management systems.

  • Crisis drills and trainings are regularly conducted with staff and students.

  • Every school has a full-time nurse on staff.

  • In partnership with the local community health system, each school has a School Based Health Center open to students and staff.

  • We partner with the local mental health agencies to provide services to students and staff.


Student Opportunities

  • We offer a wide range of programs for students, some through partnerships with Chesapeake College, Recreation and Parks, the Arts Council, and the YMCA:

  • PreK for qualifying students

  • Fine Arts including band in elementary

  • Gifted and Talented Program

  • Advanced Placement and Dual Enrollment

  • Afterschool and Summer School

  • A variety of clubs and organizations


Robert Willoughby
Supervisor of Human Resources
410.479.2894 x1140 |

Debbie Siachos
410.479.2894 x1134 |

Hannah Brewster
Human Resources Specialist
410.479.2894 x1133 |

Kimberly Purnell
Human Resources Specialist
410.479.2894 x1144 |