The first resident sisters in Whitesville were Franciscans who staffed St. Mary of the Woods School from 1882 to 1890, the year they withdrew from Kentucky. In August, 1901 in response to an appeal for sisters to reopen the school, three Sisters of Charity of Nazareth arrived, Sisters Agnes Maria Pike, Xaveria and Agnes Lucy. By September 6 the school opened with 60 students in attendance.

High School subjects were added in 1904, but there was no formal high school until 1917. During that year the faculty of four sisters moved into the new convent at O’Sullivan Hall which also included classrooms. The present grade school was completed in 1965 under Fr. Benedict Huff’s administration. The O’Sullivan building was dismantled in 1986.

For the 2009-2010 year student enrollment stands over 160. Kindergarten was added in 2007 and Pre-school in 2008. St. Mary Grade School continues to provide a quality Catholic education for students in the community.