Daughter of Derry Westenra, the fifth Baron Rossmore of Rossmore Castle, Co. Monaghan, Lady Mary Bailey (1890-1960) married the South African millionaire Abe Bailey in 1911.
Awarded her pilot’s licence in 1927, Lady Bailey left Stag Lane on a Standard De Havilland Moth with an A.D.C. Cirrus Mk. II engine of 75/80 h.p. on March 9, 1928. She reached Cape Town on April 30th after a journey of 8,000 miles. The return journey, which started in September, was made across the Belgian Congo, along the southern edge of the Sahara and up the west coast of Africa and home across Spain and France. Lady Bailey reached Stag Lane on January 16th after flying some 18,000 miles. She became the first woman to fly solo from England to South Africa. A mother of five children, she saw this act as a gesture of female independence and of faith in light aircraft.
She also flew in many international competitions and was awarded the Britannia Trophy.