Samuel Brooks Tobie Caldwell was born on 8 Jan 1792 and lived in Newburyport, MA until he was about twenty-four years old. In 1816 he wrote in his diary that he was in Leesburg, VA where he began publishing a newspaper called . The first issue of his paper was published on 10 Jan 1817. Finding the printing business very difficult, he sold it on 13 Oct 1819 to B.W. Sower. He continued to sell books and stationery supplies for several years, but found this business very dull and unprofitable. He wrote in 24 Jul 1820 that he tried to, "...settle up my business and go to the western country. The times are so hard that it is impossible to close to any advantage at this time." His diary does not say how long he continued in that business.

From 1831-1832, Caldwell represented Loudoun County in the Virginia House of Delegates. While serving in this office, Caldwell met with other prominent citizens of Virginia to found the Virginia Historical and Philosophical Society on 29 Dec 1831. In 1848 he bought a grist mill at Wheatland which he traded in 1859 for the Catoctin Mill on the south fork of Catoctin Creek. In the Census of 1850 he is listed as a merchant; in 1860, a miller. Samuel B.T. Caldwell died on 29 Mar 1866 and is buried in the Leesburg Presbyterian Churchyard.