Olive Warner Kellogg Damon was born on November 3, 19ll, in Vernon, Connecticut. She was the third of six children of Walter Edward Kellogg, a farmer, and Elinor Belle Warner. The Kellogg family moved often but finally in 1918, when Olive was seven, the family moved to the Warner family farm in Haydenville (Williamsburg), Massachusetts. She was educated in the Haydenville schools and graduated from Smith Vocational and Agricultural School in Northampton, Massachusetts, in 1931. She married Alan Wells Damon of Williamsburg in 1937. They settled in Whately, Massachusetts, where together they operated a dairy farm from 1937 to 1979. A premature son, born in 1937, died shortly after birth. A second son, Alan Wells Damon Jr. ("Pete") was born March 25, 1939. Alan Wells Damon Sr. died in 1999 and Alan Wells Damon Jr. died in 2005.

A self taught local artist, Damon painted murals and oil paintings and made more that 30,000 hand-made pressed flower cards which she sold privately, at craft fairs, and through commercial outlets. She was a founding member of the Williamsburg Brush and Palette Club, an active member of the Whately Congregational Church, the local chapter of the Daughters of the American Revolution, and the Williamsburg (Massachusetts) Grange. An avid diarist, she self published Memoirs, Things I Remember in 1999. She died September 11, 2003, at the age of 91.

Olive Damon represents a generation of women whose lives were formed by the Depression and World War II, and who lived within the confines of the daily hard work and unpredictability of rural life. Her world centered around home, family, church, and a close knit community. Despite hardships and domestic trials, Olive made a life for herself in a supportive community of extended family and women friends. In 1984 she wrote, "1984 has ended and in spite of adversities…. it was happy because I made it that way. I made up my mind to 'do my thing' as people say today and not try to change what I knew couldn't be changed.… Along with counting my blessings, I made big strides in a small business I had started a couple of years ago. This has been a great pleasure." She was especially close to her son, "Pete," with whom she kept up a lively correspondence when he was away and with whom she traveled frequently. In her final diary entry, July 2002, she writes about her wedding: "Alan told me when Dad brot (sic) me down the stairs I looked like an angel. Pete told me I have always been beautiful."