He paid town founder EW Henck $1.50 to help him fill out the paperwork for the homestead act. He was granted 77 acres that spanned both sides of what is now State Road 434 in Longwood, to the east of Rangeline Road. On the land grant, his last name is “Sheppard,” but the correct spelling is “Shepherd.”
Thomas Shepherd first came to Longwood in 1879. He was recruited to come work on the South Florida Railroad and became the patriarch of one of the pioneer black families that settled in West Longwood. He was a former slave from Georgia born in 1849 and lived to be 101.
Once he was settled in Longwood, he brought the rest of his family, including his father (Nathan Shepherd), sister (Millie Shepherd), brother-in-law (Henry Peterson), and his brother (Peter Shepherd). Peter became the first pastor at the Corinth Baptist Church, now known as Mt. Olive Missionary Baptist. One of Shepherd’s daughters married George Jones, another pioneer black family in Longwood.
Thomas was a skilled piano player. In his later years, he lived with the family of Fredrick Rand and helped care for their homes in Longwood and Orlando. He had known Rand since the day of the railroad; Rand was one of the founders.
Family’s roots firmly planted in Longwood land (Orlando Sentinel, June 3, 2001)