May Paine lived most of her life in her native Charleston, recording the Lowcountry’s beauty in impressionistic scenes and participating in local arts initiatives. An active and early member of the Sketch Club of the Carolina Art Association, Willis served as treasurer for the organization which was devoted to artists’ mutual encouragement. This affiliation enabled her to take classes with the array of visiting artists who came to Charleston at the club’s invitation. Many of these professionals were landscape painters with ties to the school in Woodstock, New York, an outpost of the Art Students League. Paine’s instructors included Henry Leith-Ross, Frank Swift Chase, Emil Gruppe, Ivan Summers, and Alfred Hutty. Primarily a landscape painter herself, Paine painted outdoors on small prepared boards enlivened by energetic brushwork and rich color. She often spent her summers in the mountains of North Carolina, a pleasant escape from the heat of Charleston.
In addition to the shows at the club’s space at the Gibbes Art Gallery, Paine exhibited seven times with the Southern States Art League. During these years, she resided with her brother M. B. Paine, a noted photographer of historic buildings and contemporary life. After her brother’s death, Paine moved to Savannah in 1940, dying there the following year. According to her obituary in a Charleston newspaper, Paine’s paintings were widely exhibited in such places as New York, Philadelphia, Washington, Atlanta, and other major cities throughout the South.