On January 10, 1854 Charles Shearer was born at Spanish Oaks, in Appomattox. Charles father- James Shearer-was a member of the slave owning family there. Matilda Giles a woman enslaved by the Shearer family was Charles’ mother. Upon becoming free in April 1865, Charles moved to Lynchburg to find work before leaving to attend Hampton Normal and Agricultural Institute in Hampton (today’s Hampton University). Charles graduated in 1880. Henrietta Merchant, Charles free and multiracial wife, was born in 1859 to Madison and Elizabeth George Merchant of Lynchburg. Henrietta too attended Hampton Institute. Charles and Henrietta married in 1884. Following their wedding, Charles taught at Hampton Institute until the two of them moved back to the Lynchburg area, where both he and Henrietta taught elementary school. In 1891 Charles and Henrietta left Virginia and for Everett, Massachusetts where they purchased a home. Charles began work in as a headwaiter in nearby Boston’s Young's Hotel and the Parker House. The Shearers joined Boston's famous long time integrated Tremont Temple Baptist Church. Charles was a profoundly religious man who deeply appreciated the education he received at Hampton Institute. He credited his success in life to his education and religious conviction. A staunch Baptist, Charles often visited Oak Bluffs, then called Cottage City, to attend religious services in Baptist Temple Park in historic East Chop. Charles and Henrietta grew to love Martha’s Vineyard and purchased their first property on the island in the late 1800's. Charles and Henrietta bought their second property at Martha’s Vineyard in August 1903. The homesite is where the Inn at Shearer Cottage now stands. In order to help support her family's summers on Martha's Vineyard, Henrietta built a one-story, open structure known as the "Long House" on the newly purchased property and started a laundry business. She hired several women and specialized in the fancywork of fluting the elaborate petticoats worn in that era. An entrepreneur, Henrietta provided pick-up and delivery service for the laundry with her horse and wagon. In 1912, the couple expanded their home opening Shearer Cottage, a sizeable inn, which was operated in conjunction with the laundry. The inn offered lodging, food, recreation and entertainment to African Americans who were not able to partake of those amenities on the island’s whites only establishments. The Shearer’s Cottage was such a success that by 1917 Henrietta was able to close her laundry business to focus solely on the Inn.