Earl Cunningham was born on a farm in Edgecomb, Maine, near Boothbay Harbor in 1893. He left home at 13 and supported himself as a tinker and a peddler. When he was 16, Cunningham, who lived in a fisherman’s shack on Stratton Island off Old Orchard Beach, began painting images of boats and farms on wood he scavenged. In the early 1910s, Cunningham sailed on one or more of the giant coastal schooners that carried coal, ice, naval stores and lumber between Maine, the mid-Atlantic states and Florida.

In 1915, Cunningham married Iva Moses. During World War I, he drove a truck for a naval yard and visited Florida for the first time. For the next 10 years, the couple spent winters in Florida — Tampa Bay, Cedar Key and St. Augustine. In 1937, troubled by marital problems, Cunningham left Maine and bought land in South Carolina, where he farmed and raised chickens.

Cunningham settled in St. Augustine in 1949, where he opened a curio shop called the Over Fork Gallery. He displayed his paintings there, although the works were not for sale. In 1969, collector Marilyn Mennello convinced Cunningham to sell her a work; and in 1970, she made possible an exhibition of selected paintings at the Loch Haven Art Center (now the Orlando Museum of Art). In 1974, Cunningham’s second museum exhibition, Earl Cunningham: American Primitive, opened at the Daytona Beach Museum of Arts and Sciences.