James Whitcomb Riley was born in 1849 in a log cabin. That cabin, constructed in 1847, is now the kitchen wing of the current house. The two story main portion of the house was built by James’ father, Reuben, from 1850-1853. Reuben Riley was a lawyer by profession and was the first mayor of Greenfield.
James’ education began at home. He would make up rhymes to amuse his mother. Once he started attending school, his teacher noticed his great interest in literature but little else. He left school at age 16 and never returned.
James spent most of his childhood in this house until the family sold the property in 1864 because of financial difficulties. However, the impact the house had upon his childhood is evident. He often used portions of the house for the settings of his writings. Little Orphant Annie was based upon a real orphan named Mary Alice Smith who stayed with the Rileys during the Civil War. She helped raise James and frequently told mesmerizing stories about ghosts and fairies to keep him entertained.
During his young adulthood, Riley spent a few years traveling the state. He eventually returned to Greenfield and worked as the editor of the newspaper there for a few months. He worked at the Anderson Democrat in 1877 and while he was there his writings received some national recognition. He then moved to Indianapolis and continued his writings there.
By the 1890s, James Whitcomb Riley had found some financial success. One of his first acts was to purchase his childhood home, which he did in 1893. He leased the house to various tenants until 1912. After that, his sister-in-law, Julia, ran the property. She maintained it until 1916. In 1935, the city of Greenfield purchased the house and it has served as a museum ever since.