1868 – He was born on August 23 of this year in Garnett, Kansas, where his father had briefly moved to set up a law practice.
1880 – His family moved to Lewistown, Illinois, where he attended high school and had his first publication in the Chicago Daily News.
1889 – He attended The Knox Academy from this year until 1890. A defunct preparatory program run by Knox College, but was forced to leave due to his family's inability to finance his education.
1898 - He married Helen M. Jenkins, the daughter of a lawyer in Chicago, and had three children. He published several other volumes of poems including Book of Verses in this year.
1903 – During his law partnership with Clarence Darrow, from this year until 1908, Masters defended the poor.
1911 – He started his own law firm, despite the three years of unrest (1908-1911) due to extramarital affairs and an argument with Darrow.
1914 – He truly began developing as a notable American poet, when he began submitting a series of poems (this time under the pseudonym Webster Ford) about his childhood experiences in Western Illinois, which was published in Reedy's Mirror, a St. Louis publication.
1915 – His series was bound into a volume and re-titled Spoon River Anthology.
1936 – He was awarded the Mark Twain Silver Medal this year.
1941 – He was awarded at the Poetry Society of America medal in this year.
1942 – He was awarded at the Academy of American Poets Fellowship.
1944 – He received an award in the Shelly Memorial Award in this year.
1950 – He died March 5 of this year. He was buried in Oakland cemetery in Petersburg, Illinois.
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- "Genius is a bend in the creek where bright water has gathered, and which mirrors the trees, the sky and the banks. It just does that because it is there and the scenery is there. Talent is a fine mirror with a silver frame, with the name of the owner engraved on the back."