Although it was along the National Road, the residence was described as being near lots of woodland animals, but very few people. The front porch had two doors. The left led into the family parlor, while the right door led to Reuben Riley's law office. The influx of visitors to Reuben Riley's office gave James Whitcomb Riley a chance to learn how to entertain several people at a time with speeches and tales, as his father had. Visitors such as a ragged man and an orphan girl, Mary Alice Smith (Little Orphant Annie), inspired James Whitcomb Riley to write the poems he would later tell in his adulthood. Reuben had organized a militia of Greenfield residents during the American Civil War. However, his involvement with the War hurt his law career, forcing him to sell the house in 1870. In 1893 James Whitcomb Riley bought the house, but kept his residence in Indianapolis, at what is today James Whitcomb Riley Museum Home. Although James Whitcomb Riley never again lived in Greenfield house, his brother John and John's wife resided there; James would often visit them. It was on one of these visits in 1898 that James Whitcomb Riley called Greenfield the best town outside of Heaven.
Before his death in 1916, Riley wrote over 1000 poems, including Little Orphant Annie, When the Frost is on the Punkin, and the The Bear Story. During his time, he was regarded as more important than Mark Twain. The city of Greenfield bought the property in 1936, creating the Riley Old Home Society to run the property.
The Riley home is now operated as a museum by the Riley Old Home Society and the City of Greenfield, through the Greenfield Parks and Recreation Department. The museum is open to visitors, several thousand a year, from April through November, usually closed for the winter. An adjacent home, the Mitchell House, was where James Whitcomb Riley's poem publisher John Mitchell lived. Mitchell's former domicile is used as a museum, allowing for Riley's home to be kept as it would have looked like during his time of residence.
The garden behind the Riley house is frequently enjoyed by visitors during the seasons of spring and summer. Since 1991 this garden has been developed and maintained by the Greenfield Herb Society. An annual festival celebrating James Whitcomb Riley's connection with Greenfield is celebrated in first Thursday through Sunday in October.
For more on James Whitcomb Riley, visit the Clio entry: James Whitcomb Riley Home.