It was Maya Angelou who said that all great achievements require time. Lady Mary Bailey was a late bloomer in the aviation industry. But when she finally took flight, her reputation as an aviator remained solid for the remainder of her life.
LADY MARY BAILEY: EARLY LIFE
Mary Westenra was born in London in 1890 but spent most of her childhood in her father’s home county of Monaghan in Ireland. Westenra is not a typical Irish name but is instead an anglicised version of the Dutch Wassenaar. Her father inherited the title of Lord Rossmore.
Mary’s mother came from a wealthy and well-connected family in London; the then Prince of Wales (later King Edward VII) was a family friend. Later in life, Mary’s stepson married Winston Churchill’s daughter.
By all accounts, Mary loved her adventurous Irish childhood. She became an accomplished horse rider and motorcyclist. She moved in London high society circles, meeting and eventually marrying widower Sir Abraham (Abe) Bailey in 1911.
Abe was South African born of British parents and became the largest landowner is what is now Zimbabwe. He was a gold mine entrepreneur and was equally well-connected, counting Winston Churchill and Cecil Rhodes as good friends. The couple travelled between South Africa and London, and facilitated behind the scenes political meetings at their London house for their politician friends.
When Lady Bailey returned to England in 1916, she joined the war effort as a driver and a mechanic.
In 1918, she returned to London from France when she became pregnant again – Mary’s first child was born in 1913.
TAKING FLIGHT
When all five of Mary’s children started boarding school, she began taking flying lessons in London. Lady Mary Heath was one of her instructors. Lady Bailey took her first solo flight in 1926, gaining her ‘A’ Certificate in 1927 which she used to enter competitions.
She became good friends with Geoffrey de Havilland, aircraft engineer and co-founder of the de Havilland Aircraft Company. De Havillands were her choice of aircraft.
Among Lady Mary Bailey’s aviation achievements are:
- She was the first woman to enter the King’s Cup race.
- She co-piloted the flight, with Louie de Havilland, which broke the world altitude record in July 1927.
- She was the first woman to fly solo across the Irish Sea.
- She was awarded the 1927 and 1928 Harmon Trophy for the world’s outstanding female aviator. Charles Lindbergh won the 1927 trophy in the male category.
But the aviation achievement that Lady Bailey is most noted for is her solo return journey from London to Cape Town. She was the first woman to fly from London to Cape Town, doing so in March/April 1928. This trip combined with her return journey was the longest solo flying achievement up to then. She flew to Cape Town via East Africa and returned via West Africa.
Her epic journey was not without its problems. The British authorities refused to let her fly over southern Sudan by herself. Dick Bentley eventually accompanied her. She misjudged her landing at Tabora Airport and crashed. A new plane had to be purchased.
Inclement weather at the start of her return journey, in May 1928, caused the plane to crash land. Although Geoffrey de Havilland arranged for a replacement plane, she could only recommence her journey in September 1928.
She faced difficulties from the French authorities in West Africa. She experienced engine problems, and poor weather in France. She finally landed back in London on 16th January 1929, ten months after embarking on her heroic adventure.
FURTHER AVIATION LIFE
Lady Bailey continued as an aviator, competing in races and studying for her ‘B’ Commercial licence. In 1930, she was awarded a DBE, the first female aviator to become a Dame.
She carried out survey flights for archaeological and geological surveys, and flew campaign posters around the UK for Prime Minister MacDonald. In 1933, she attempted to break the London to Cape Town record but abandoned the journey near the Sahara desert.
She acted as consultant in the development of civil aviation in Ireland while Abe supported the development of civil aviation in South Africa.
Abe died in South Africa in 1940 with Lady Mary unable to attend his final days due to World War II. Her second war effort was as part of the women’s auxiliary air force. Both of her sons were WWII fighter pilots.
Lady Mary Bailey retired to Cape Town where she died in 1960.
Interested in reading about more pioneering aviators? Then have a look at my biographies of Lady Mary Heath and Lilian Bland.
Arrivals Hall 