Charlotte Wynn Pyles Crum, one of the area's early white settlers, is the first known burial in Brooksville Cemetery. Born in 1792 near Savannah, Georgia, she married Col. Samuel Robert Pyles, who in 1824 moved his family to what later became Alachua County, Florida. After Pyles died in 1837, Charlotte married Richard R. Crum, who secured this portion of land through the Armed Occupation Act of 1842 and settled at Chuccochattie, less than one mile south. On September 12, 1842, while traveling nearby with her daughter Rebecca Harn, granddaughter Mary Catherine Harn, and escort John Francis McDonnell, the party was fired upon by Seminoles who were unaware the Second Seminole War had ended and were evidently retaliating for recent aggressive acts by white settlers seeking to remove the area's native population. In the struggle that followed, all escaped except Charlotte, who was killed; her death, coming immediately after the war, drew sensationalized attention and became symbolic of the conflict among diverse cultures for control of Florida's expanding American frontier. She was buried less than one-eighth mile from her home in a grave once entombed with brick.