Wilson was born in Parker, Pennsylvania in 1850. In his teens, he moved to Pittsburgh and, with little formal training, he became a self-taught painter and poet. Wilson eventually traveled to and settled in Frankfort, Kentucky, where he achieved his greatest fame. In 1901, Wilson married Anne Hendrick, daughter of General William J. Hendrick, a former Attorney-General of Kentucky, during a visit to New York. Wilson moved from Kentucky to New York in 1904, and died there in 1916. His body was returned to Frankfort for interment, which he considered his home. He is buried in Frankfort Cemetery near the grave of Daniel Boone.
As a painter, Wilson is best known for his landscapes of the Kentucky countryside.
Wilson found success as a poet, publishing poems in the major monthly magazines of his day, including Harper's Magazine. Perhaps his most famous poem is "Remember the Maine", based on the battle cry that spurred the United States into the Spanish–American War. While his martial poetry met the spirit of the times, Wilson was best known during his day as a nature poet.
After achieving success as a poet, Wilson tried his hand at prose fiction, publishing Until the Day Break in 1900.