Tara Fischer

Staff Writer

​(Oct. 29, 2026) With the Worcester County Board of Education’s District 1 and District 6 positions contested, voters in Pocomoke and Bishopville may cast their ballots next week for their preferred school system representative.​

As voters head to the polls on Nov. 3, some will be able to choose who they want to serve on the county’s board of education.

Contested races are taking place in District 1, which covers much of southern Worcester and is anchored by Pocomoke City, and District 6, which covers Bishopville, northern Berlin, and portions of Ocean Pines.​

District 6, Background​

Jackie Cutlip, the board’s current District 6 seat holder, is looking to retain her position against challenger Kathy Cater. Cutlip was appointed as the board’s District 6 representative after Katie Addis’s early resignation late last year.​

Cutlip studied criminal justice and early education at community college before opening Bayside Boat Rentals in Ocean City with her husband. The couple has owned and operated the business for over 25 years.

“I’m proud of our years of hard work, commitment, and perseverance that have led us to a business that has stood the test of time in a seasonal tourism town, serving an estimated 30,000-plus customers each summer and becoming a local favorite along the way,” Cutlip said.

Cutlip has three daughters, one in sixth grade and another in 11th grade enrolled in Worcester County Public Schools, which she believes sets her apart from her competitor.

Cutlip said that she has spent 15 years involved in WCPS as a volunteer, parent, advocate, and PTA president.

“My face has been a familiar and consistent positive presence in our schools since day one,” she said.

Former WCPS employee Kathy Cater is challenging Cutlip for the board of education’s District 6 position.

Cater moved to Worcester County more than 35 years ago and currently lives in Bishopville. She and her husband raised their two sons in the area.

Cater said she began her three-decade-long career in public education as a classroom teacher. She spent the final 16 years as an assistant principal at Stephen Decatur High School and retired in 2021.

Cater served as assistant principal at Parkside High School, Mardela Middle School, and Mardela High School, and as a conflict resolution/human relations liaison at James M. Bennett High School.

Cater maintains that her community connections set her apart. Her oldest son, Brandon Cater, is the current theater teacher at SDHS, and her granddaughter attends Buckingham Elementary School.

Additionally, while raising her sons through the school system, Cater said she served on Stephen Decatur Middle School’s School Improvement Advisory Committee and has coached Berlin Little League and local soccer programs.

District 6, Important Issues

On the school system’s pressing issues, Cutlip said she is always willing to ask tough questions in public to promote transparency and accountability.

“I believe we can be proud of our school system while still acknowledging where improvements are needed,” she said. “Recognizing our challenges does not diminish our successes. It gives us an opportunity to become even better.”

Cutlip said she believes a challenge WCPS faces is rebuilding public trust, alluding to an embezzlement scheme discovered in 2025. Former assistant superintendent Denise “Dee” Shorts pleaded guilty last month to one count of felony theft of over $100,000.

Shorts used Title I funds, money set aside for low-income students, to buy personal items like clothes, cosmetics, and furnishings for a vacation home, and altered the invoices to make it appear the dollars were spent as intended.

As part of Cutlip’s plan to regain the community’s confidence, she said communication must be open and proactive, and families and staff should be informed before worries escalate.

One of Cater’s concerns is the decline of WCPS’ competitive salary scale and the recruitment and retention of high-quality teachers and staff.

She said if elected, she intends to work collaboratively with the local government to ensure the school system’s presented budgets are fully funded “in order to maintain the level of achievement that we have been known for statewide.”

“Not only to offer competitive salaries, but to do so without sacrificing the programs that are necessary to support the levels of success we have been able to achieve,” Cater added. “That will not continue to happen without fully funding our school system.”

Cater also said she will prioritize students’ education and safety, adding that young learners should be at the center of every board of education decision.

“We need to understand the diverse needs of our student population and provide them with what is necessary to achieve their desired goals,” Cater said.

District 6, Priorities

Safety is a top priority for Cutlip. She said she intends to push for stricter disciplinary procedures if elected to the board.

“I am a huge supporter of firmer, more consistent discipline at every level,” she said. “We need more meaningful consequences that reflect real-world accountability … Every child deserves support, but no child’s behavior should prevent others from learning.”

Cutlip added safety ensures students may learn in a disruption-free environment. She also wants to maintain WCPS’ reputation as a top-performing school district and include teachers and staff in major decisions.

“Worcester County Public Schools doesn’t consistently rank among the top school systems in Maryland for no reason,” she said. “…We truly have an amazing school system with so much for all of us to be proud of, but that doesn’t mean there isn’t room for improvement.”

Cater’s agenda champions small class sizes and recruiting and retaining high-quality educators and support staff, which she said are vital to student success. She also said she advocates for physically and emotionally safe schools to keep student learning the focus every day.

Cater also hopes to prioritize compliance with educational requirements and listen to families and residents when they bring concerns to the board. Additionally, she plans to keep looking for ways to advance WCPS’s success.

“Our school system is the best in the State of Maryland, and I want to work to make sure it stays that way,” Cater said. “It is what draws people from all over to want to reside in our community. That doesn’t mean that we can’t always be looking for ways to make improvements.”

District 1

Caroline Bloxom would bring a 40-year career in education to the board. Of that time, 30 years were spent with the local system.

Bloxom taught middle and high school mathematics for 14 years. She later became a curriculum planner at Pocomoke Middle School, then served as the WCPS PreK-12 mathematics coordinator and professional development coordinator, and returned to Pocomoke Middle School as principal, a role she held for 12 years.

In 2012, Bloxom became principal of Worcester Technical High School and the district’s Career and Technology Education Coordinator. She retired in 2018.

“I understand the challenges teachers face because I have been a teacher,” Bloxom said. “I understand the responsibilities of school administrators because I have led schools. I understand the importance of curriculum, instructional quality, staff development, and career preparation because I have worked directly in each of those areas.”

Bloxom continues to be involved with the community, particularly with the Delmarva Discovery Museum and the Worcester County Library Foundation.

District 1’s other contestant, Glen Ennis, is a retired Maryland teacher and administrator with 30 years of experience, mostly in Somerset County. Ennis grew up in Pocomoke and graduated from Pocomoke High School.

Ennis worked as a classroom teacher, vice principal, and principal of a career and technical center. He was named Somerset’s Teacher of the Year in 2002. Ennis also served on the State of Maryland task force to update middle school curriculum.

Ennis is a bus driver for students throughout the county. His work as a driver includes everyday pickup, field trips, nighttime athletic events, and summer school.

“I’m really familiar with the county because when everyone gets on the bus, they like to talk,” he said.

District 1, Important Issues

Bloxom said effective communication is necessary for a functioning school system. If elected, she said she will maintain an open dialogue with her constituents, explain policies, and answer questions.

Bloxom noted that securing top-notch teachers and support staff remains a critical issue for WCPS. She said the board must prioritize these educators’ concerns and provide them with the tools and resources they need.

The candidate said she would push for a continual review of instructional programs to guarantee students are prepared for not only graduation, but life beyond school.

Bloxom said she would also be a responsible steward of taxpayer dollars, if selected to the board.

“Educational decisions should be made with careful consideration of student needs, available resources, and long-term fiscal responsibility,” she said.

As for Ennis, he believes the board should recruit and retain high-achieving teachers and staff through competitive salaries and benefits.

Ennis said WCPS has fallen behind in hiring and retaining qualified educators because nearby counties, even those with lower test scores like Somerset County, offer more attractive compensation packages.

Ennis also said the board of education should take a closer look at the budget and cut wasteful spending. He noted that during the Covid-19 pandemic, the federal government offered more grants than in the past, and now that those dollars are used up, the school system has absorbed the costs of programs implemented during that time. Some of those programs may no longer be needed.

District 1, Priorities

Additional priorities for Bloxom include physical and mental safety for students and staff, stronger partnerships between the school system and its stakeholders, responsible budgeting, and student achievement.

Bloxom said she intends to prioritize education “that builds strong academic skills, encourages critical thinking, and prepares students for life after graduation.”

“I have always believed that one of education’s greatest responsibilities is teaching children how to think, not what to think,” she added.

Ennis said he would like to encourage more students towards the trades instead of college and push for higher enrollment at Worcester Technical High School.

He said that students are coming out of college with debt and a job unrelated to their major. He also maintained that trades are facing a shortage.

“I think what we’ve come to now is we are in a desperate shortage of trades people and we have a lot of kids in college debt not doing what they got a degree in,” Ennis said.