Sherwood's paternal grandfather was a judge and a Senator and his grandmother, who was also a skilled musician, had ancestry traces back to the English nobility.

Mary Balis Sherwood was a well-educated woman, born near Catskill, New York where she grew up in a home that had been given to her great-grandfather for service in the Revolutionary War.

Recognizing this challenge, Sherwood drafted his own manipulations of the joints within his thumbs, practiced slowing and accurately, and over time was able to successfully demonstrate his octave exercises to Kullak.

[5] Sherwood's most successful and popular concert recognition comes after the 1872–1873 winter season, when he performed Ludwig van Beethoven’s “Emperor” Concerto, No.

Fay was an accomplished pianist in her own right, having excelled under a number of piano teachers in America and Germany and moving on to public performances.

Sherwood and Fay spent about six months in Weimar, Germany where they had the privilege of hearing and studying under the guidance of Franz Liszt, who offered to act as their eldest daughter's godfather.

[4] However, their marriage ended in divorce, and Fay even sued Sherwood for child support in April 1886 after he had neglected to pay on an order from November 1885.

Sherwood remained the president of his school and the director of the piano department at Siegel-Myers until he suffered a stroke and became bedridden from paralysis in late 1910.