Notice Fort Loudoun on left side of this map drawn in 1777, by a Hessian captured in the Battle of Trenton New Jersey.
Above is a 1777 map with the current streets superimposed.
This map is available at the on the Old Town Loudoun Street outdoor mall.
Unfortunately this map is cropped off. On the bottom right of the map above is a statement by the Hessian Prisoner, Lt Andreas Wiederholdt in 1777:
"Plan of the small town of Winchester located in Frederick County in Virginia, which was founded only about 25 years ago, at a time when there was still war with the Indians. From that time, can still be seen, the remains of the fort where General Washington, then Colonel, commanded and himself defended."
Below is the original 1777 map without the modern streets superimposed.
Only correction needed so far for this map are the dates on construction of Fort Loudoun. Construction began May 1756 and mostly through 1758 and some work later.