Greenfield began in 1841 where the town's site was selected as the place for Dade County's first courthouse. A pioneer couple, Matthias and Mary Ann Allison, gave the county fifty-one acres "in consideration of the location of the county seat". A year later the courthouse was finished and Greenfield's first business had opened all on the new town's square.
Greenfield, called the "Gate City of the Grotto" in early history, grew as the emigrants from Kentucky, Tennessee and the Carolinas, were lured by the wooded hills, fertile valleys and a wonderful abundance of water in the streams and springs.
Visitors to Greenfield see the square lined with brick buildings built in the 1880's - with bricks made in the Greenfield Brickyard. The Opera House, which opened in 1888, was called the "Jewel of the Square".
The Greenfield High School, the oldest high school in Southwest Missouri, opened in 1889. Other historic buildings include three churches built in the late 1800s and early 1900s are still used for worship.
A Mecca for history buffs and seekers of family history is the Dade County Library housed in a historic house. The Library has a large collection of Missouri history plus the Dade County Genealogical Society is also housed in the Library with extensive research materials available.