Thompson was born in Randolph County, North Carolina, and graduated from the University of North Carolina. He served as a high school principal at Concord High School in Concord, North Carolina from 1895–99, where he wrote an essay about the transformation of southern culture from a rural agricultural to textile/manufacturing way of life that he witnessed while an educator in Concord. This essay, in part, gained Thompson admittance to Columbia University where he received his Ph.D. in 1901, and became a full professor of history at City College of New York.
In 1905, Thompson married Isobel Graham Aitken of New York and they had one son, Lawrence.
Thompson, while professor at CCNY, was among the leading scholar/historians of the social and industrial transformation of the New South in the early decades of the 20th century.
- From the Cotton Field to the Cotton Mill: A Study of the Industrial Transition in North Carolina (1906). New York: Macmillan. OCLC 16411826
- The New South: A Chronicle of Social and Industrial Evolution Yale Chronicles of America Series (1919). New Haven: Yale University Press. OCLC 17361006
- The Age of Invention: A Chronicle of Mechanical Conquest (1921). New Haven: Yale University Press. OCLC 3616164
- "Holland Thompson, 1873-1940". Retrieved 2008-05-19.
- Works by Holland Thompson at Project Gutenberg
- Works by or about Holland Thompson at Internet Archive
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