Hi Denise,

I think the Loudoun register of free negroes will answer some of your questions.

Pricilla Elizabeth CROSS (otherwise called JONES, daughter of Pricilla CROSS

freedom proved by oath of George WOODARD
abt 20 yrs old 5 ft 7 and a half tall, bright mulatto color, small scar on the right eyebrow, also a very dark spot on the side of the right ear.

Date: 13 Nov 1855
Record # 2306
page 197

there are three other CROSS registry entries under her - also JONES for James Madison 20, Jesse 12 and Victoria 9.

Earlier in the registry is her mother:

CROSS, Priscilla (alias BISICKS)
freedom proved by oath of Jane Gibbons.

abt 30 years old 5 ft 4 1/2 tall, light complexion, little freckles about the nose, and has two minute scars above the right eye

Date 9 Nov 1847

Record # 1455
Page 70

right under her listing is (they must have come in and registered together)

CROSS, Rowena (alias Bisicks) freedom proved by oath of Jane Gibbons
about 26 years old 5'5'. dark complexion, plain scar above the hand on the left wrist, another above the right eye in the forehead, another in the left eye brow and one across the upper part of her nose.

9 Nov 1847
Record # 1455
page 70

There was no Jane Gibbons in Loudoun - there was one listed in census for 1830:

Name: Jane Gibbons
Township: Not Stated
County: Prince Edward
State: Virginia

1840:

Name: Jane Gibbon
Township: Eastern District
County: Prince Edward
State: Virginia

1850

Name: Jane Gibbons
Age: 45
Estimated birth year: abt 1805
Race: White
Gender: Female
Home in 1850
(City,County,State): Not Stated, Mathews, Virginia

I would explore this family - since either Jane emancipated her - or knew who did.