Born in Baltimore and raised on Robert Street, he was a 1947 Frederick Douglass High School graduate. He earned a bachelor's degree at Lincoln University and a law degree at Howard University, where he was a founding editor of its law journal.
Family members said that while a student at Howard, he witnessed Thurgood Marshall in a moot court argument of the landmark Brown vs. the Board of Education case.
They said Mr. Woolford was a former neighbor of Justice Marshall's in the Sandtown section of West Baltimore and he received a letter of recommendation from Justice Marshall's mother, Norma, to attend Howard.
"He had witnessed an incident of police injustice as a child and wanted to work for justice," said his wife, the former Sadie Alston, a Baptist pastor active in Columbia.
She said they met working together in the 1950s at a downtown Baltimore law firm where he was a clerk. She had just moved to Baltimore and on a subsequent Sunday, he took her to the Union Baptist Church, where they later married and where, in 2010, they renewed their vows at a ceremony covered by The Baltimore Sun.
In 1956, he was sworn in as a lawyer in Annapolis. He then formed a law firm, Howard, Woolford and Leeds, on Pleasant Street.
In 1965, Mr. Woolford became an early African-American attorney in the Social Security Administration's Office of the General Counsel. He served for nearly 30 years, family members said.
During the administration of President Gerald R. Ford, Mr. Woolford was named to the Presidential Clemency Board.
Mr. Woolford's "work product has been superlative and of such quality that his case summaries have been considered among the most comprehensive and best written by our staff reviewers," wrote Charles E. Goodell, the board's chairman.
In 1970, Mr. Woolford, who had been living in Pimlico, decided to leave Baltimore and buy a new home in Columbia.
"It was a bold move and we wanted to be a part of what was being called the new America," his wife said. They moved with their children and his widowed mother.
Family members said he met and formed a friendship with Columbia's founder, James W. Rouse. "He worked for the betterment of the county because he believed in Rouse's dream of integration and unity," Mrs. Woolford said.
Howard County Executive Omar Jones named Mr. Woolford to the county Human Relations Commission in April 1972. A few months later, he became its chairman.
In a 1973 Sun article, Mr. Woolford said the county's school board and superintendent were "blocking" an investigation. He contended that "the school officials definitely do not want a full disclosure of the processes they use in classifying students in regard to learning disabilities." Other articles detailed his role in investigating alleged discrimination against female county employees. He also sought to have more African-American teachers hired, family members said.
He accompanied a Sun reporter to a bar in rural Howard County, where black and white patrons voluntarily occupied different parts of the same building. The article said Mr. Woolford was served "politely" in the white section and "the barmaid called him 'Sir,'" but the taproom remained segregated.
He was then quoted in the article: "You know, we may not have a law case, but that bar tells a lot about race relations in this country."
In a 1973 Washington Star article, Mr. Woolford cited an incident that he said epitomized the black experience in Columbia. "He recalls playing cards one night with a white neighbor who happened to mention that he had voted for Sen. Barry Goldwater in 1964," the news story said. "Woolford said he immediately reacted because of what he considered the Republican candidate's racial views, and the discussion became heated for a time. 'Then I thought, if we both still were living [elsewhere], we'd never even have talked about it.'"
Mr. Woolford served on the Executive Committee of the Columbia Foundation in the late 1970s. In 1977, he worked with Mr. Rouse in planning aspects of Columbia's 10th birthday celebration.
"You played a special part in our festivities as Chairman of the [Columbia] Forum that gave our 'newcomers' a peek into the early planning of their city through the eyes of the original work group," Mr. Rouse wrote in a letter to Mr. Woolford in 1978.
In 1974, he became a founding member of the Columbia chapter of the Kappa Alpha Psi fraternity. He also acted in Howard County theatrical productions, including the role of mayor in "Day of Absence."
He was a lifetime member of the National Association for the Advancement of Colored People and a member of Mensa.
Funeral services will be held at 11 a.m. Wednesday at St. John the Evangelist Baptist Church of Columbia, 9055 Tamar Drive, a congregation he helped found.
In addition to his wife of 51 years, survivors include a son, Llewellyn W. Woolford Jr. of Washington, D.C.; and two daughters, Pamela W. Woolford and Johnetta Woolford, both of Columbia.