In 1866, Fletcher entered Pembroke College, University of Oxford and graduated in 1869 with a Bachelor of Arts (second class honours).

In 1875, Fletcher had emigrated to Australia and began working as a teacher at a private school called Oaklands, at Mittagong, New South Wales.

During this period, Fletcher met Anne Marian Clarke, whom he married at St Thomas's Church of England, North Sydney.

Fletcher was involved in the establishment of soccer clubs in the Blue Mountains and from 1891 to 1894, served as President of the Katoomba School of Arts.

In 1893, a major economic downturn forced Katoomba College to close, and Fletcher joined the Bar that same year.