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.
The Cunningham Family, Boothbay Harbor, Maine circa 1917. Fourth and fifth from left: Charles and Elwilda, Parents of Earl. Sixth from left: Earl Cunningham. Click on thumbnail to view larger image.
Captain Earl Cunningham on the Hokona in 1916. Click on thumbnail to view larger image.
Written by Earl Cunningham on the back of the photograph: "The Nellie G near her landing, Boothbay Harbor, Maine 1909". Click on thumbnail to view larger image.
Written by Earl Cunningham on the back of the photograph: "1912 Taken by me on River Kennebec from ferry. Note ice in river". Click on thumbnail to view larger image.
Written by Earl Cunningham on the back of the photograph: "I came from Portland Me to B. B. Harbor here on The Grace, and watched this big hotel known as the MENAWARMET burn. I saw it afire inside, then the fire streamed out of the Sailor's Walk, where the flag is. Burned flat, everything. Captain Foster's Daughter and I went to the fire 'round 9 O'clock at night. June 1913". Click on thumbnail to view larger image.
Dirigo, The Good Barge, Earl Cunningham's camp car photographed in Freeport, Maine July 16, 1921. Written by Earl Cunningham on the back of the photograph: "July 16, 1921 Auto in yard, Freeport, me our Camp Car We Went to Florida in Earl Cunningham". Click on thumbnail to view larger image.
Earl Cunningham photographed standing on the Dixie Highway between Jacksonville and St. Augustine, Florida in 1922. Written on the back of the photograph: "Dixie Highway between Jacksonville and St. Augustine, Fla.". Click on thumbnail to view larger image.
Earl Cunningham photographed with his dog in Cartersville, Georgia on April 30, 1922. Written on the back of the photograph: "Cartersville, Ga Apr 30, 1922. Earl Cunningham and dog". Click on thumbnail to view larger image.
Earl Cunningham photographed his camp in Anastasia, Florida, September 1923. Written on the back of the photograph: "Our camp Anastasia Fla The camp car we went to Florida in Earl Cunningham". Click on thumbnail to view larger image.
Maggie Cunningham photographed at Anastasia, Florida in 1923. Written on the back of the photograph: "Storm covering (street) car track 5ft deep in sand 1923 Maggie my wife Earl Cunningham". Click on thumbnail to view larger image.
Earl Cunningham photographed at Anastasia, Florida in 1923. Written on the back of the photograph: "Sand dunes on Anastasia, back of St. Augustine Beach Fla 1923 Earl Cunningham". Click on thumbnail to view larger image.
Earl Cunningham 1916. Written on the back of the photograph: "Earl Cunningham 1916". Click on thumbnail to view larger image.
Written on the back of the photograph: "Product of our farm 1916". Click on thumbnail to view larger image.
Written on the back of the photograph: "Harraseeket River Earl Cunningham 1916". Click on thumbnail to view larger image.
Written on the back of the photograph: "Cap'n sitting on a sand hill filled by the wind 1917 Captain Earl Cunningham". Click on thumbnail to view larger image.
Written on the back of the photograph: "1919 Everette Pratt and Earl Schenectady N.Y." Click on thumbnail to view larger image.
Written on the back of the photograph: "1919 Bertha on top of wheels. Fla. Near St. Augustine on Dixie Highway. Earl Cunningham" Click on thumbnail to view larger image.
Written on the back of the photograph: "E. R. Cunningham on the top of Fort Marion, St. Augustine Fla. July 1924" Click on thumbnail to view larger image.
Written on the back of the photograph: "E. R. Cunningham beside the hot shot furnace at Fort Marion, St. Augustine Fla. July 1924" Click on thumbnail to view larger image.
Written on the back of the photograph: "Aug. 16 1942 garage and outbuildings this is some of my carpenter work" Click on thumbnail to view larger image.
Written on the back of the photograph: "Aug. 6 1921 Niagara Falls Have to come down 23 flights of stairs 10 steps to a flight to get to the foot of the falls or can go down on an elevator " Click on thumbnail to view larger image.
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