Solomon Henkel once owned the house that stood on this property, but after it burned down, Henkel moved his family down the road where they built a brick house. Several other buildings stood on this lot afterwards, including: the original Henkel Printing Press.
In 1869 Jessie H. Rupert received funds from the 34th Massachusetts Veterans, the Freedmens’ Bureau, and Massachusetts friends to build the Cottage Institute for Young Ladies. The institute was a day and boarding school, and at night acted as the Woodworth Cottage for African Americans. Woodworth Cottage was supported by the American Missionary Association of New England and continued through until 1874.
After the school closed, Rupert traveled often, but the building remained her home until she died in 1909.