Page 259 - Family History

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Round Hill, VA – Early History

By Eugene Scheel
A Waterford historian and mapmaker.
Early Settlers

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
A 1945 postcard
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

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