Ena Collymore was born in Spanish Town, Jamaica, which was the Spanish capital of Jamaica until 1655, and then the British capital of Jamaica until 1872, when it moved to Kingston. In other words, a large, long-established city. When she was born, the typical life path for a girl was to leave school by 12-14, and any job would likely to be domestic work, or even more difficult physical labor in plantation fields: sugar was still the dominant estate crop in Jamaica at the time. Otherwise it was marry and bear children. Collymore had a strike against her in that her father, a railway stationmaster, died when she was young, but on the plus side her mother moved the family to Kingston to find better work. Her mother found it: she was a postmistress (the period’s official title for a female postmaster). Her two sisters dropped out of school to work, but Ena was able to finish high school …and then her mother died.
Collymore took a room at the YWCA, and got a job as a bookkeeper at a bakery. When she saw a temporary job as an administrative clerk in the courthouse, she applied, but was turned down because she was female. She apparently argued well, because the manager relented and gave her the job on a trial basis. The trial proved her worth, and she stayed on not just as a temp, but was made a permanent administrative clerk of the Kingston Criminal Court. Then World War II struck, and Collymore enlisted with the Auxiliary Territorial Service of the British Army, and assigned to the stenography pool in Jamaica. No, she said; she insisted on being assigned overseas. They sent her to England. “When I got to England, they offered me an office role typing, but I told them that I hadn’t joined up just to type!” She wanted to work an anti-aircraft gun! The Army met her halfway, training her as a radar operator — the first West Indian, male or female, to become a radar operator in the British Army; she served in Belgium and the U.K., with her final position being in the War Office in London.
After the war she stayed and studied law at The Honourable Society of Gray’s Inn, one of four legal “Inns” in London going back to the 1300s. Membership in an Inn is still a requirement to become a barrister (court attorney) or judge in the U.K. Her only university training was a side course in juvenile delinquency at the University of London. She was called to the Bar in 1948 — meaning she was declared proficient in practicing law — then returned to Jamaica and the courthouse in Kingston. There, Collymore was appointed a Deputy Clerk of Courts, which sounds like the same thing, but rather than being administrative, the Clerk of Courts is a professional legal position. She also married and had three children — and kept being promoted, including to Clerk of Courts, and finally to Assistant Crown Solicitor. In all these positions, she was the first woman to hold the post in Jamaica. Once the Juvenile Courts of Jamaica were formally introduced, Collymore-Woodstock was appointed chair of the Eastern Circuit, and later rose to Senior Resident Magistrate for St. Andrew Parish. In 1975 she was honored as an officer in the Order of Distinction for her contributions to the justice system of Jamaica. She retired from the bench in 1977, but continued to serve post-retirement in the Turks and Caicos and in Anguilla.
On the side during her legal career, Judge Collymore-Woodstock served as a District Commissioner for the Girl Guides, the British equivalent of the Girl Scouts. She was honored as a member of the Order of the British Empire in 1967 for her work with the Girl Guides. In 2020 she was recognized as the oldest surviving female veteran of the British Army — at 103. One of her daughters, Marguerite Woodstock-Riley, followed in her mother’s footsteps and is now a King’s Counsel in Barbados. Ena Collymore-Woodstock died on December 2, at 108.