After studying at Manchester Polytechnic, where she gained a BA in 1975 and MA in 1976, Caroline Bailey taught until the 1980s when she started to paint in watercolour  full-time. She has had major solo exhibitions in London and elsewhere, and here in Broadway since 1995. Selected group exhibitions include the Royal Institute of Painters in Watercolours, the Royal Watercolour Society, the Royal Glasgow Institute and the Royal Scottish Society of Painters in Watercolours, to which she was elected member in 1998.

Caroline Bailey's awards include the NS Macfarlane Charitable Trust Award at the Royal Scottish Academy in 1999, the Glasgow Arts Club Fellowship at the Royal Scottish Society of Painters in Watercolours 1999, and the Scottish Society of Painters in Watercolours 2001.