Middlesex County in 1755
Source: Library of Congress, A map of the most inhabited part of Virginia containing the whole province of Maryland with part of Pensilvania, New Jersey and North Carolina (by Joshua Fry and Peter Jefferson, 1755)
Middlesex County was created in 1669.1
It is named after the Middlesex region in England north of London. That land was occupied by Saxons after the Romans abandoned England in 410 CE. Different groups of Saxons occupyied lands to the east and south. Land occupied by the "East Saxons" ended up being "Essex," land occupied by the "South Saxons" ended up being "Sussex," land occupied by the "West Saxons" ended up being Wessex," and the land occupied by the Saxons in the middle became known as "Middlesex."2
Jackson Creek before World War II
Source: National Archives, Virginia - Jackson Creek and Virginia - Jackson Creek