After 58 years in public education, ‘Skip’ Oakley looks back on career

Skip Oakley

BY STEFANIE JACKSON, Eastern Shore Post —

William “Skip” Oakley witnessed many major changes to the public school system in his 58 years in education, including 48 years as a teacher and administrator and a decade on the Northampton County School Board.

Oakley, age 83, declined to run for re-election in 2023 and decided to give someone younger a chance to serve the community and bring fresh ideas to the table.

“I think you reach a point in time when you can stay too long, and I didn’t want to do that. I didn’t want to stay too long,” he said.

Oakley is an Eastern Shore native and spent most of his youth in lower Northampton County. He attended Cape Charles and Cheriton elementary schools and Northampton High School, from which he graduated in 1959.

His graduating class was the first to have spent all four years of high school at Northampton High, which was built in 1954.

Oakley attended Louisburg College, in North Carolina, and considered becoming an engineer, which was a popular major in the 1950s, he said.

He soon realized he didn’t want to be an engineer and thought back to his time at Northampton High School.

Oakley was “greatly influenced” in his decision to pursue a career in education by his former physical education teacher, George Young, who later was a longtime superintendent of Northampton County Public Schools.

Oakley’s college major was physical education, with minors in science, history, and geography.

He received both a bachelor’s and a master’s degree from East Carolina University, in Greenville, N.C.

Oakley returned to the Shore in 1964 and began teaching his minor areas of study at Northampton High School. He also was an assistant coach in football, basketball, and track and field.

But in 48 years, Oakley never taught physical education. The opportunity never arose, in part because he became a principal early in his career, after just five years.

A master’s degree was required to become a principal, and few educators had one then, he said.

Oakley became the principal of Birdsnest Elementary School, where he also was a 7th grade teacher.

He explained that there was no middle school in Northampton County then. Elementary school included grades 1 to 7 and high school included grades 8 to 12.

At the time, the county had more elementary schools with fewer pupils – Birdsnest Elementary averaged 90 to 100 students, Oakley said — so school employees often wore many hats.

He returned to Northampton High as principal from 1969 to 1971.

Around that same time, Northampton County fully integrated its schools, with Black and White children receiving the same public education.

Oakley said the adults “fought it for a right good while, but it was a smooth transition.”

“It wasn’t a major deal with the students,” he said. “Many of the adults had problems with it, but the students had no trouble.”

After his time as principal at Northampton High, Oakley went to Salisbury, Md., and spent 30 years working for Wicomico County schools.

He came back to the Eastern Shore of Virginia and spent a decade working in Accomack County, first as the last principal of Mary N. Smith Middle School before it closed its doors in 2004, then as an assistant principal at Arcadia Middle School, and finally as the principal of Arcadia Middle.

Oakley retired after 48 years as a teacher and school administrator, yet his career in education wasn’t quite over.

The first year that the Northampton County School Board transitioned from an appointed board to an elected one, Oakley ran for a seat on the school board and won.

He was re-elected twice and served a total of 10 years. (Northampton school board members have staggered terms and Oakley initially served a two-year term.)

He was “excited” to learn that Northampton County decided to move forward with renovation and new construction at its high and middle school complex at the Northampton High campus in Eastville.

He recalled telling Supervisor John Coker, upon hearing the news, “I’m just glad now we have finally quit kicking the can down the road and we’re going to go ahead and get something accomplished.”

Although Oakley was no longer a school board member when the contract was awarded, many will remember him as an advocate for the project throughout his 10 years on the school board.

“I enjoyed my 10 years, and it was a good way to close out my career. … I guess if I look back, I’d do it all over again,” Oakley said.

After spending 58 years in education, he plans to celebrate his 58th wedding anniversary with his wife, Carole Oakley, in April.

The couple has three children, nine grandchildren, and four great-grandchildren. The Oakleys look forward to the arrival of their fifth great-grandchild in July.

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