Warrenton had its origin at the junction of the Falmouth-Winchester and Alexandria-Culpeper roads, where a trading post known as the Red Store was established. At the time of the Revolution a settlement had begun, and by 1790 the first courthouse was built, a jail was erected and an academy named for General Joseph Warren, a Revolutionary War hero, was founded. Richard Henry Lee donated 71 acres of land for the county seat, which was incorporated as the Town of Warrenton in 1810.

The Orange and Alexandria Railroad, which ran through the county, had strategic significance because it was part of the only rail link between Washington and Richmond. It was also part of rail connections to the Shenandoah Valley, Charlottesville, Lynchburg, and into Tennessee. From Lynchburg, the Virginia and Tennessee Railroad connections accessed lead mines near Wytheville, Virginia, and the lead provided raw material for the bullets of the Confederate Army. By the 1850's a railroad reached the town, which boasted several churches, thriving mercantile establishments, a weekly newspaper, one or two schools and William “Extra Billy” Smith’s Monte Rosa estate. Because of Warrenton’s location the town was considered for its size in 1860 (604 population) “as the richest town in the whole South."

3.1 Postal Service

In 1827 William “Extra Billy’ Smith established a line of United States mail and passenger post coaches through Virginia, which he then expanded into the Carolinas and Georgia in 1831. He pursued a wider stagecoach service and steamboat enterprise connecting Richmond and Baltimore, Pensacola and Galveston, Norfolk and Baltimore by steamer. He managed and ran his “pony express” postal service routes from Monte Rosa and the large Italianate barn and associated buildings on the same property in Warrenton, Virginia.

The Second Continental Congress of 1775 established the United States Postal Service and Benjamin Franklin was appointed as the first postmaster general. As the postal service became a vital means of communicating in an ever growing nation, its importance was recognized in 1872 the USPS when it was elevated to a cabinet-level department. It was the administration of President Andrew Jackson that awarded Smith with his first postal service contract to deliver mail between Washington, D.C., and Milledgeville, Georgia (then the Capital of Georgia). Ambitious, Smith grew that service by adding other mail routes, for which he charged “extra” postal fees. During an investigation of the Post Office Department, Smith's “extra” fees caught the attention of U.S. Senator Benjamin W. Leigh. Thereafter, he was familiarly known as "Extra Billy".

Reportedly, Smith was a shrewd businessman and a master at running his postal service routes. This became a fairly lucrative business venture. The postal service, coupled with the railroads, stage coaches and electric telegraph, were the only means by which information and news could be sent out large distances across the new growing nation. Both railroads and telegraph lines are linear and limited to developed and accessible areas; whereas, pony express and postal riders were far more versatile and could transverse most terrains to deliver correspondences and news. As a result, the “pony express” postal services played a key role is disseminating information and the growth of the country.

3.2 Union Army Use

During much of the Civil War the boundaries of control moved back and forth. Second only to Winchester VA, control of Warrenton change hands between the Union and Confederate forces sixty-seven (67) times due to its central geography and proximity to major transportation routes. As a result, Monte Rosa saw both Union and Confederate forces camped on its land using its facilities to manage and guide their war efforts.

As the Union forces advanced through the south they restored Warrenton to the union. A succession of Union Generals took up camp beside the house and used the stable block for their horses. With Smith away and leading the Confederate 49th Virginia Volunteers, Mrs. Smith at Monte Rosa tread a fine line between captive and hostess. The Smith household and the Union generals reached a kind of understanding. The Smith family were treated with respect and the women tried to be gracious in order to save their homes and stock. This approach often did not work out as many homes in the south were destroyed, but Elizabeth Smith was successful in her purpose.

Early in the war, General James McDowell bivouacked and his clerks slept and worked in the Library.

Other Union officers came to Monte Rosa – Major General Pleasanton and Custer and Sedgwick.

Pleasanton and Custer had their portraits painted with Neptune as a backdrop. Custer has extensive and elaborate gold military ribbon going from the cuff up the arm as a symbol of power and vanity.

3.3 Confederate Army Use

The Army of the Shenandoah, Brigadier General Joseph E Johnson, Col J.E.B. Stuart 1st VA Cavalry, Col. A.C. Cumming VA Volunteers bivouacked at Monte Rosa having moved up from the south. They were guests at Monte Rosa and stabled their horses using the time to make preparations before the Battle of Bull Run. They set out from Warrenton Junction on the Orange and Alexandria Railroad to Manassas.

3.4 Notable Visitors

Some of the notable figures that are known to have come to Monte Rosa during Extra Billy’s life include, but are not limited to the following:

Governor William "Extra Billy" Smith (September 6, 1797 – May 18, 1887)
11th President James Knox Polk (November 2, 1795 – June 15, 1849)
14th President Franklin Pierce (November 23, 1804 – October 8, 1869)
General Robert E. Lee (January 19, 1807 – October 12, 1870)
Major General George Armstrong Custer (December 5, 1839 – June 25, 1876)
Major General Irvin McDowell (October 15, 1818 – May 4, 1885)
Major General John Sedgwick (September 13, 1813 – May 9, 1864)
Major General Alfred Pleasanton (July 7, 1824 – February 17, 1897)
Brigadier General Joseph Eggleston Johnston (February 3, 1807 – March 21, 1891)
Brigadier General Eppa Hunton II (September 22, 1822 – October 11, 1908)
Brigadier General William Henry Fitzhugh Payne (January 27, 1830 – March 29, 1904)
Colonel John Singleton Mosby (“The Gray Ghost”) (December 6, 1833 – May 30, 1916)
Colonel Charles Marshall (October 3, 1830 – April 19, 1902)
Colonel James Keith "Jimmy" Marshall (April 17, 1839 – July 3, 1863)