Robert W. Caldwell was born about 1822. Caldwell began his career as a farmer and shipped produce to Philadelphia markets by rail from West Chester. In 1860, he purchased a Locust Grove Village general store at sheriff’s sale. Robert Caldwell, or his children, ran this store from 1860 through 1930. Robert Caldwell’s occupations included farmer, market man, shopkeeper, and postmaster. His vocations included: assessor and collector of taxes for Pocopson; director and treasurer of the Pocopson School Board; and delegate to the first Republican County Convention in 1855.