The Keswick area, and Albemarle County as a whole, is unusually blessed with an impressively intact system of historic roads. While roads are often seen a mundane, they are in fact one of the main forces that determines how a region develops. Throughout its approximately 270-year history, the roads that have developed in the Keswick region have been directly responsible for much of Keswick’s present appearance. … Historic roads were almost always built in order to connect two existing destinations using the shortest possible route, and the early roads in Keswick were often built to provide routes for moving plantation products (mostly tobacco and wheat) to ports along the major rivers of the region.

The first road to be built in the area was Route 250, or, as it was called, “The Mountain Road.” The Mountain Road was officially established in 1733 and was one of the first three roads to be built in what is now Albemarle County. Peter Jefferson, Thomas Jefferson’s father, was one of the first surveyors for the road and is largely responsible for laying out its course from just west of Charlottesville to the lower end of Goochland. Mountain Road, or “Three Notch’d,” as it was renamed in 1742, was developed to connect the newly patented plantations along the Southwest Mountains with the more developed tidewater region. Because Peter Jefferson’s home plantation of Shadwell was located along this road, and since a large, busy road would dramatically increase the value of his land, he was strongly motivated to lay out the best road he could. And, as seen by the immense amount of traffic that continues to utilize Route 250, he did indeed lay out a great road. It has srved as one of the main and one of the busiest routes in to Charlottesville ever since its founding.

Routes 22 and 231 also follow the courses set by roads laid out in the 18th century. The pre-1742 road was initially called the “Fredericksburg Road” because it, unsurprisingly, led to Fredericksburg. Originally starting at the corner of Keswick Road and East Keswick Drive (at the location of La Fourche, a building that once served as a tavern for the heavily traveled Three Notch’d Road), the road was an important connection to Fredericksburg’s busy port on the Rappahannock River. Route 22 after it leaves Cismont and heads toward Louisa was originally known as the “Old Mountain Road.” Old Mountain Road was established between the mid-1730s and 1742 and was built to connect the Nicholas Meriwether patent with the town of New Castle, a tobacco port the Meriwethers established on the South Anna River. This road later acquired further significance because it ran through the agriculturally productive Green Springs region of Louisa County, resulting in a large increase in traffic leading to New Castle and beyond....