Lindsay studied medicine at Ohio’s Hiram College from 1897 to 1900, but he did not want to be a doctor; his parents were pressuring him toward medicine. Once he wrote to them that he wasn’t meant to be a doctor but a painter; they wrote back saying that doctors can draw pictures in their free time. He left Hiram anyway, heading to Chicago to study at the Art Institute of Chicago from 1900 to 1903. In 1904 he left to attend the New York School of Art (now The New School) to study pen and ink. Lindsay remained interested in art for the rest of his life, drawing illustrations for some of his poetry. His art studies also probably led him to appreciate the new art form of silent film. His 1915 book The Art of the Moving Picture is generally considered the first book of film criticism, according to critic Stanley Kauffmann, discussing Lindsay in For the Love of Movies: The Story of American Film Criticism.

While in New York in 1905 Lindsay turned to poetry in earnest. He tried to sell his poems on the streets. Self-printing his poems, he began to barter a pamphlet titled Rhymes To Be Traded For Bread, which he traded for food as a self-perceived modern version of a medieval troubadour.

From May to September 1912 he traveled—again on foot—from Illinois to New Mexico, trading his poems for food and lodging. During this last trek, Lindsay composed his most famous poem, “The Congo”. Going through Kansas, he was supposedly so successful that “he had to send money home to keep his pockets empty”. On his return, Harriet Monroe published in Poetry magazine first his poem “General William Booth Enters into Heaven” in 1913 and then “The Congo” in 1914. At this point, Lindsay became very well known.

Subtitled “A Study of the Negro Race” and beginning with a section titled “Their Basic Savagery”, “The Congo” reflects the tensions within a relatively isolated and pastoral society suddenly confronted by the industrialized world. The poem was inspired by a sermon preached in October 1913 that detailed the drowning of a missionary in the Congo River; this event had drawn worldwide criticism, as had the colonial exploitation of the Congo under the government of Leopold II of Belgium. Lindsay defended the poem; in a letter to Joel Spingarn, Chairman of the Board of Directors of the NAACP, Lindsay wrote that “My ‘Congo’ and ‘Booker T. Washington Trilogy’ have both been denounced by the Colored people for reasons that I cannot fathom…. The third section of ‘The Congo’ is certainly as hopeful as any human being dare to be in regard to any race.” Spingarn responded by acknowledging Lindsay’s good intentions, but saying that Lindsay sometimes glamorized differences between people of African descent and people of other races, while many African-Americans wished to emphasize the “feelings and desires” that they held in common with others.

Growing up in Springfield influenced Lindsay in other ways, as evidenced in such poems as “On the Building of Springfield” and culminating in poems praising Springfield’s most famous resident, Abraham Lincoln. In “Lincoln”, Lindsay exclaims, “Would I might rouse the Lincoln in you all!” In his 1914 poem “Abraham Lincoln Walks at Midnight (In Springfield, Illinois)”, Lindsay specifically places Lincoln in Springfield, with the poem’s opening:

Lindsay’s private life was rife with disappointments, such as his unsuccessful courtship in 1914 of fellow poet Sara Teasdale before she married rich businessman Ernst Filsinger. While this itself may have caused Lindsay to become more concerned with money, his financial pressures would greatly increase later on.

Lindsay himself indicated in the 1915 preface to “The Congo” that no less a figure than William Butler Yeats respected his work. Yeats felt they shared a concern for capturing the sound of the primitive and of singing in poetry. In 1915, Lindsay gave a poetry reading to President Woodrow Wilson and the entire Cabinet.

Most contemporaries acknowledged Lindsay’s intention to be an advocate for African-Americans. This intention was particularly evident in the 1918 poem “The Jazz Birds”, praising the war efforts of African-Americans during World War I, an issue to which the vast majority of the white US seemed blind. Additionally, W.E.B. Du Bois hailed Lindsay’s story “The Golden-Faced People” for its insights into racism. Lindsay saw himself as anti-racist not only in his own writing but in his encouragement of a writer; he credited himself with discovering Langston Hughes, who, while working as a busboy at a Washington, D.C., was at the restaurant where Lindsay ate and gave Lindsay copies of his poems.

In 1924 he moved to Spokane, Washington, where he lived in room 1129 of the Davenport Hotel until 1929. On May 19, 1925, at age 45, he married 23-year-old Elizabeth Connor. The new pressure to support his considerably younger wife escalated as she bore him daughter Susan Doniphan Lindsay in May 1926 and son Nicholas Cave Lindsay in September 1927.

Lindsay, a versatile and prolific writer and poet, helped to “keep alive the appreciation of poetry as a spoken art” whose poetry was said to “abound in meter and rhymes and is no shredded prose”, had a traditional verse structure and was described by a contemporary in 1924 as “pungent phrases, clinging cadences, dramatic energy, comic thrust, lyric seriousness and tragic intensity”. Lindsay’s biographer, Dennis Camp, says that Lindsay’s ideas on “civic beauty and civic tolerance” were published in 1912 in his broadside “The Gospel of Beauty” and that later, in 1915, Lindsay published the first American study of film as an art form, The Art of The Moving Picture. Camp notes that on Lindsay’s tombstone is recorded a single word, “Poet”.

Crushed by financial worry and in failing health from his six-month road trip, Lindsay sank into depression. On December 5, 1931, he committed suicide by drinking a bottle of lye. His last words were: “They tried to get me; I got them first!”

In 1932, Edgar Lee Masters published an article on modern poetry in The American Mercury that praised Lindsay extensively and wrote a biography of Lindsay in 1935 (four years after its subject’s death) entitled Vachel Lindsay: A Poet in America.

The Illinois Historic Preservation Agency helps to maintain the Vachel Lindsay House at 603 South Fifth Street in Springfield, the site of Lindsay’s birth and death. The agency donated the house to the state, which then closed it for restoration at a cost of $1.5 million. As of October 8, 2014, the site was again open to the public, with guided tours available on Thursday through Sunday from 1 to 5 pm. Lindsay’s grave lies in Oak Ridge Cemetery. The bridge crossing the midpoint of Lake Springfield, built in 1934, is named in Lindsay’s honor.

Desperate for money, Lindsay undertook an exhausting string of readings throughout the East and Midwest from October 1928 through March 1929. During this time, Poetry magazine awarded him a lifetime achievement award of $500 (equivalent to about $7445 in 2012 dollars). In April 1929, Lindsay and his family moved to the house of his birth in Springfield, Illinois, an expensive undertaking. In that same year, coinciding with the Stock Market Crash of 1929, Lindsay published two more poetry volumes: The Litany of Washington Street and Every Soul A Circus. He gained money by doing odd jobs throughout but in general earned very little during his travels.