About Mary Bailey
Lived 1890 – 1960 (aged 69). Mary Bailey was a British aircraft pilot and engineer.
Dame Mary Bailey, Lady Bailey, ( Westenra; 1 December 1890 – 29 July 1960) was an Anglo-Irish aviator. She was known as one of the finest aviatrixes of her time, who '"personally guided a plane from England to the nether tip of South Africa and back"
Early life The Hon Mary Westenra was the only daughter of Derrick Westenra, 5th Baron Rossmore, of Rossmore Castle, County Monaghan and his wife, Mittie (née Naylor). She had two brothers.
She spent most of her childhood in Ireland where she was taught by governesses after running away from school in 1906. Adventurous from a young age, she apparently bought a motorbike in her youth and was gaining a reputation for speeding in cars by 1914. She became the first woman to fly across the Irish Sea.
Between 9 March and 30 April 1928, Bailey made an solo flight from Croydon to Cape Town, flying a Cirrus-engined de Havilland DH.60 Cirrus Moth with an extra fuel tank which gave an endurance of about 10 hours. At about the same time (January to May 1928), Lady Heath was flying solo from Cape Town to the UK.
She then made the journey back between September 1928 and 16 January 1929. The return journey involved flying across the Belgian Congo, then along the southern edge of the Sahara and up the west coast of Africa, then across Spain and France back home again. It was the longest solo flight and longest flight accomplished by a woman that far. This feat won her the 1929 Britannia Trophy.
In 1927 and 1928, she twice won the Harmon Trophy as the world's outstanding aviatrix. She also participated in the Challenge International de Tourisme 1929, which she completed off the contest, and Challenge International de Tourisme 1930, in which she took 31st place for 60 participants, being one of only two women.
In 1930 she held a seat on the Women's Engineering Society Council. In 1931, she became a member of a group of female pioneers for science, the members of which shared her adventurous and determined spirit. She also attained the rank of Section Officer in the Women's Auxiliary Air Force, during World War II.
Contributions to archaeology Bailey was also able to use her talents for aviation to take aerial photographs of important archaeological sites. She was very likely the first woman to accomplish this during her work in February 1931 on the Kharga Oasis project in Egypt. They had five children including Sir Derrick Bailey, 3rd Bt. (15 August 1918 – 19 June 2009) a fighter pilot cricketeer and businessman and James R A Bailey (23 October 1919 – 29 February 2000) fighter pilot, writer and co-founder of Drum magazine.
Don’t just read it —
keep it.
Full-length biographies made to live with: read them, listen on the way to work, watch them tonight.
- E-book
- Audio
- Video
Instant download · yours to keep · every purchase keeps this site free
Important facts
Family & relationships
People in Mary Bailey's life
Named in this biography and alive at the same time
Contemporaries
People whose lives overlapped Mary Bailey's
Frequently asked questions
Who was Mary Bailey?
Anglo-Irish aviator (1890-1960)
When was Mary Bailey born?
Mary Bailey was born on 1 December 1890 in Rossmore Castle.
When did Mary Bailey die?
Mary Bailey died on 29 July 1960 in Kenilworth.
What was Mary Bailey's occupation?
Mary Bailey was an aircraft pilot and engineer.
What nationality was Mary Bailey?
Mary Bailey was British.
Sources & further reading
· DBpedia: Mary Bailey (aviator)
Cite this page
APA: Biography.guide. (2026). Mary Bailey. https://biography.guide/mary-bailey/
MLA: "Mary Bailey." Biography.guide, https://biography.guide/mary-bailey/.
Chicago: "Mary Bailey." Biography.guide. https://biography.guide/mary-bailey/.
Data last updated: 2026-09-22 · Spot an error? Report a correction.
Page generated 2026-09-27 05:31 UTC