Major Wilkins was born around 1859 in Warrenton, (Warren County) North Carolina. Wilkins worked as a laborer. Wilkins was charged with larceny on February 22, 1875, and sentenced to two years in the North Carolina State Penitentiary. Wilkins was recorded in the North Carolina State Penitentiary's Descriptive Register for the Years 1869-1884 as prisoner number 1105. In his marriage records, Wilkins’ race is listed as “colored.” Wilkins was sixteen years old when he was arrested. Wilkins was noted as possessing no formal education, meaning he could not read or write at that time. He escaped from the prison on August 10, 1875, and was recaptured on August 22, 1875. During his incarceration, Wilkins was leased to the Western North Carolina Railroad Company to work on railroad construction. He was discharged from the railroad on March 27, 1877. Wilkins married Laura Pitts on April 19, 1887, in Halifax (Halifax County), North Carolina.