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The hill itself is a 910-foot high knob two miles southwest of town. In pre-1722 years its summit was a camping place for Indians traversing the "plain path" - as the Indians called their trails - from the Shenandoah Valley to their main north-south migration route along today's Route 15. The 1722 Treaty of Albany forbade the Indians to migrate east of the Blue Ridge, and thereafter the gentle slopes and summit of the Round Hill became farmland, once again to become a camping and listening place during the Civil War. Shortly, the hill again took its present appearance as farmland, and by the early 20th century it was also called Round Top - to distinguish it from the newly-established town.

Thomas sixth Lord Fairfax granted Benjamin Grayson the first tract of land in today's Round Hill in 1731, with Grayson's grant on the west side of Main Street, north of the old railroad. Within a decade Grayson sold the parcel to speculator John Tayloe the younger. The land on the east side of Main Street was granted to William Cox in 1741. In the same year Thomas Gregg was granted today's downtown as part of a fair-sized tract that ran east into Purcellville.

There was no town of Round Hill, however, in any sense of the word, until 1858. The area's leading community was Woodgrove, two miles north of Round Hill, for by 1777 the main road west from Leesburg intersected the present Round Hill-to-Hillsboro Road at Woodgrove. This road did not take the right-of-way of present Route 7 because of the swampy lowlands of the three main branches of the North Fork of Goose Creek which outline the western and eastern approaches to Round Hill.

With the building of the Leesburg and Snicker's Gap Turnpike, today's Route 7, in 1832-1833, the situation changed, and by 1857 Guilford C. Gregg had opened a store at the northwest corner of the pike and the road to Woodgrove. On March 25, 1858, the U.S. postal department opened its Round Hill Post Office, and Gregg was appointed first postmaster, a position he held under the Confederate States of America, and which he was forced to relinquish with the coming of the occupation government, on Sept. 29, 1866. But on Jan. 16, 1868, in the twilight of Andrew Johnson's presidency, there again was a Round Hill postmark, and a less controversial postmaster in the person of William B. Chamblin.