Kester was born in 1870, some 30 miles north of Columbus at Delaware, Ohio. He was the younger of two sons raised by Franklin "Frank" Cooley and Harriet Kester. His father was traveling salesman, and mother an art teacher who in 1882 helped found the Cleveland School of Art. Kester was educated by home tutors and at private schools where he excelled in the dramatic arts. His first success came in January 1892 with Countess Roudine, which premiered in Philadelphia at the Chestnut Street Theatre and opened a week later at the Union Square Theatre in New York City. Countess Roudine was a collaborative effort written with the actress Minnie Maddern Fiske. In 1896 his adaptation of Edward Bulwer-Lytton's Eugene Aram was produced by Walker Whiteside's company and in 1902 with George Middleton adapted the George W. Cable Southern romance The Cavalier that was staged at the Criterion Theatre with Julia Marlowe. Actress Annie Russell produced and starred in his 1906 Quaker tale Friend Hannah, written with the help of his brother, Vaughan. Kester worked on nearly 30 plays over his career. His most successful Broadway effort was probably The Woman of Bronze, which ran for 252 performances between September 1920 and April 1921 at Manhattan's Frazee Theatre. He also authored a number of books, with His Own Country most likely the more popular. Described as shy and diffident, Kester preferred country life to that of the city. In 1902, with his brother, he purchased and renovated Woodlawn Plantation in Northern Virginia. Five years later the two acquired nearby Gunston Hall, where Vaughan Kester died in 1911. A few years later Kester and his mother relocated to Belmont, an estate near Alexandria, Virginia, which is today part of the campus of St. Stephen's & St. Agnes School. Kester spent his final years at Lake Mohegan, a small community near Peekskill, New York. He died there in 1933 at the age of 62, a victim of thrombosis. At the time the closest surviving member of his family was the mezzo-soprano opera singer Florence Wickham, a cousin. He is buried in the graveyard at Pohick Church, once the parish church of Gunston Hall, as is his mother; at one time he had served as a member of the church vestry.
Kester spoke of his novel His Own Country in the aftermath of World War I:
The Race problem is always with us, and as my story deals in a serious way with its more serious aspects, I do not think it can be untimely. New phases of this great problem come up from day to day – but the problem itself is as old as history – very likely it will remain a problem to the end of history. Racial differences and the prejudices resulting from them have always confronted practical statesmen. The old method of dealing with them was by conquest, subjugation, or extermination. Such methods are now obsolete. Better ones must be found. Understanding must precede intelligent action along any lines, and my reason – perhaps I would better say my justification – for writing His Own Country has been my hope and belief that it would bring some little considered phases of this menacing and mighty problem more clearly before the minds of readers who live remote from it, yet whose consent is necessary, as it should be in a democracy, to any adjustment of settlement of living conditions where the races are existing side by side.
"Home"
I want to go home To the dull old town With the shaded streets And the open square And the hill And the flats And the house I love And the paths I know - I want to go home. If I can't go back To the happy days, Yet I can live Where their shadows lie, Under the trees And over the grass - I want to be there Where the joy was once. Oh, I want to go home, I want to go home.