2026 Apr-May Community News

As we move into one of the busiest and most exciting times of the school year, I want to thank our families and community for the energy and commitment you bring to our schools. The beautiful spring weather has arrived, and with it comes a full calendar of events. Spring concerts are scheduled at every school, and classrooms are buzzing with activities and celebrations. Our high schools are also preparing to honor the Class of 2026 as graduation approaches.

This week, we celebrate Staff Appreciation Week. Each school plans their own special and creative ways to say thank you to staff, and the district will join in by bringing refreshment vendors to visit our buildings. I hope families will also take a moment to express their gratitude, whether with a quick thank you or a note of appreciation, to the staff who make a difference in their child's life every day. Our teachers, bus drivers, counselors, custodians, administrators, and so many others work tirelessly to support students, and this is a wonderful time to let them know how much they are valued.

To stay up to date on everything happening across the district, please continue to check the Caroline Schools app, social media, and the district and school websites. There’s so much to look forward to this season!

Derek L. Simmons, Ed.D.

Superintendent

For specific school events, please visit your school's app or website.

May 5 - Board of Education Meeting

May 14 - SECAC Staff Appreciation Celebration

May 19 - Board of Education Work Session

May 25 - Schools & Offices Closed for Memorial Day

May 27 - Colonel Richardson High School Graduation

May 28 - North Caroline High School Graduation

June 2 - Board of Education Meeting

June 17 - Last Day (Half Day!) for Students

June 19 - Schools & Offices Closed for Juneteenth

See All District Events

Start your summer planning now with a FREE PROGRAM for rising 6th, 7th 8th and 9th graders!

Summer Career Enrichment Program

• Session I: July 6 – July 16
• Session II: July 20 – July 30

Location: North Dorchester High School in Hurlock

Free bus transportation

Breakfast & lunch provided

This program will engage students in hands-on activities that lead to career paths in cybersecurity, media arts, video design, health, computer science, and engineering.

Classes offered will include: Animation, App Development, Chess, Cyber Security, Drones, Media Arts, Presentation/Graphic Design, and Robotics.

The program is in partnership with People for Change Coalition, Mid-Shore Regional Council, Rural Maryland Council, and Caroline, Dorchester, and Talbot County Public Schools.

For more info: contact@pfcoalition.org, 310-772-1552

2025 program photos courtesy of Connie Connelly, Caroline Review

Our first Business & Community Update meeting was a great success as local business leaders and community partners joined us to learn about what’s happening in Caroline County Public Schools. We walked through highlights of our 2025–2030 strategic plan and shared updates on budget priorities, Community Schools work, the Blueprint for Maryland’s Future, and Work-Based Learning Continuum initiatives that help students gain real-world experience. The group was engaged, asked great questions, and genuinely appreciated the chance to connect. We’re already excited to build on this idea next year and bring even more voices to the table.

Presentation

Our second annual Community Schools Partners & Vendors Network Meeting brought a full house and the spirit of collaboration. Administrators and Community Coordinators from all nine schools attended, joined by a wide range of community partners committed to supporting students and families.

The Supervisor of Community Schools and Equity Nicole Fisher opened the event with a warm welcome and an overview of the Community Schools strategy, highlighting its benefits, framework, and the collective impact they achieve.

Superintendent Derek Simmons reaffirmed the mission of Community Schools, emphasizing that the work would not be possible without strong partnerships. “You all help us build those connection points that enable wraparound services for our families,” he noted.

Director of Administrative Services Rob Willoughby also addressed attendees, explaining that while Caroline County Public Schools’ security requirements for individuals entering buildings to work with students may be more extensive than those used by some organizations, these enhanced measures are essential to ensuring student safety.

Following the opening remarks, schools, partners, and vendors had the opportunity to connect, discuss needs and services, and explore ways to strengthen collaboration in the year ahead.

Presentation Event Photos on Flickr

Want to learn more about Community Schools? Visit our website for information!