Skip to main content
Winter Park Library Archive

1892 ~ 1948

Erland (Earl) Ronald Cunningham was born in Edgecomb, Maine near Boothbay Harbor. He was the third child of six born to Charles and Elwilda Cunningham. His family lived and worked on the family farm that had been in the family since the early nineteenth century.
In 1905, at the age of thirteen, Earl left home to make his way in the world. He worked as a tinker and peddler selling or trading old beads, pocket knives, and other odds and ends. About 1909 he was living in a fisherman's shack on Stratton Island off Old Orchard Beach, Maine. He acquired some paints and painted on salvaged wood washed in from the sea. He painted pictures of boats, New England farm scenes and sold his paintings for fifty cents each. He acquired a sailboat and sailed to within fifteen miles of New York City, to Jamaica Bay, Sandy Hook, Long Island Sound, and up beyond the narrows of the Hudson River.
In 1912 he graduated from the Hamlin-Foster Company School of Automobile Engineering in Portland, Maine. Later he studied coastal navigation and received a license to work as a harbor and river pilot. He sailed on large schooners rigged with four and five masts that traveled up and down the East coast carrying coal, naval stores and other cargo, stopping at ports from Maine to Florida. These experiences, along with family stories about the sea, would provide material for his later paintings.
On June 29, 1915, Earl Cunningham and Iva Moses, a piano teacher, were married. Throughout their marriage Earl called her "Maggie." They purchased a thirty-five foot cabin cruiser named "Hokona" and lived aboard.
Between 1918 and 1936 the Cunninghams divided their time between Maine and Florida. They earned a living digging for Indian relics, collecting opalized coral, and catching fiddler crabs which Earl preserved and took back to Maine to sell. They continued to call Maine home and maintained a twenty-five acre farm there called "Fort Valley". Earl continued to paint.
Sometime shortly after 1936 the couple divorced. In 1940 Earl sold his Maine farm and purchased a fifty-acre farm in Waterboro, South Carolina. When World War II erupted the farm was converted to raise chickens for the U.S. Army. Earl continued his painting.