At the Stoopley-Gibson farm, where buildings have existed since at least 1670 and the manor house was likely built by the Bright family in 1860, Henry Massey was born into slavery around 1835 to the Bright family. In 1845, Joseph Bright inherited Henry as one of five of twenty-eight enslaved people from his deceased father. As the Bright estate broke up and Joseph Bright faced financial problems, Henry feared being separated from his family and sold off the island, so he planned his escape. In October 1849, at age 14, he fled the farm and made his way into Pennsylvania, where he lived near Harrisburg for five years until authorities arrested him in September 1854 under the Fugitive Slave Law. He was taken to Philadelphia for trial, where Franklin Bright claimed him and returned him to the Bright family farm as a slave. Records show that he later married a woman named Amaud, had a daughter named Mary born in 1863, and appeared in 1880 as a literate house servant in Dixon, Maryland.