Bernard Howard was born into slavery in 1789 and lived on the nearby Needwood Forest property, where he was involved in the daily operations of Needwood Farm, a successful enterprise owned by Mary Digges Lee Gouverneur that in 1850 produced 800 bushels of wheat, 1000 bushels of Indian corn, 100 bushels of oats, 100 pounds of wool, 50 pounds of honey, 200 pounds of butter, as well as potatoes, beans, hay, and orchard products. He labored on the Needwood property until gaining his freedom in Maryland on November 1, 1864, when the new Maryland Constitution freed enslaved people in the state; by then, he, his wife, and children, including his oldest child Daniel, about twenty, and his youngest, Judson, six, were free after lifetimes of forced labor. Bernard Howard remained in the area after emancipation and began farming, purchasing 5 acres in 1869 from Mary Gouverneur, his former enslaver, and building a small stone house three miles away that later passed to his daughter Julia Ann Smothers. Bernard and his wife Sarah lived in the home they built nearby and often shared it with their children and grandchildren, while two of their oldest children, Daniel and Julia, continued working on farms throughout the area. Daniel's daughter Mary later worked as housekeeper and cook for the Charles Flook family on this property for many years, and her niece Regina Thomas recalled coming to the farmhouse to help her aunt. Julia worked on the nearby Lee farm as a housekeeper and helped care for the family's children, who knew her as Aunt Julie; she married John Smothers and raised her family nearby. One of Julia's sons, Charles Smothers, played baseball in the Black Baseball League for the Yales of Brunswick. Bernard Howard continued working in local agricultural production until about 1880, when his health prevented further labor, and he died on July 17, 188 having spent nearly 80 years helping grow and harvest the region's agricultural goods. Other farms in the region, including the Gouverneur and Hilleary farms, also benefited from the agricultural knowledge that members of the Howard family passed on for generations.