Provided by Timothy Youmans, Planning Director and amateur local historian
The streets in the Old Town area of the city were named by Colonel James Wood back when he, as Winchester’s first Clerk of the Court for Frederick County, created the original 30-lot plat for Winchester in 1744. Lord Fairfax also created many of the streets in Old Town in the late 1750s. Dr. Garland Quarles, in his book “The Streets of Winchester, VA, The Origin and Significance of Their Names” provides an explanation for what these original streets were named for.
Beyond the rigid grid of downtown streets laid out by Wood and Fairfax, other roads had a less planned configuration and branched off of old roads, some of which evolved from native American hunting routes like the road we know of as Valley Avenue today. During the time of early European settlement in the Valley, this became known as the Great Wagon Rd providing access for settlers coming down from PA to points south and west of Winchester. Other roads were established under direction of colonial government or by old farming families seeking to connect outlying communities and/or adjoining farms. Thus, roads like Millwood Ave evolved from the turnpike leading to Millwood in present-day Clarke County. Berryville Avenue evolved from the Berryville Turnpike leading to the Town of Berryville.
Over time, individual developers or investment companies would present surveys to the City government to lay out new streets extending off of the major roadways that today bear major U.S. Route numbers like US 11, 17, 50 and 522. These U.S. routes include Valley Avenue, Amherst Street, Fairmont Avenue, and Millwood Avenue. The new side streets were often developed for residential neighborhoods such as the ones that branch off of Valley Avenue south of John Handley High School. Sometimes developers would choose names for historical figures like Thomas Jefferson or Daniel Morgan. Others would name the streets for family members such as the streets that the Henry family developed off of the east side of Valley Ave, including Montague, Roberts, and of course, Henry Street.
When Dr. Quarles prepared his book of Winchester Street names in the late 1950s, he listed 108 streets. Much expansion occurred in the City between then and the early 2000s when I took on the task as City Planning Director and amateur historian to create an updated history of street name origins. Part of this increase in road names was due to development within the old City limits, but a large part of the increase was due to the major annexation in the early 1970s that dramatically expanded the City to the south and the west.
Today, there are nearly 450 publicly owned and named streets and alleys along with 91 privately owned and named streets and alleys. Of those, about 120 are named for local persons such as the developer’s family members. About 70 streets are named for natural things like trees, flowers, topographic features and rocks. There are 57 streets named for Civil War figures, mostly private streets in the Meadow Branch subdivision named by the developer for Confederate generals. Another 39 streets are named for persons or places in England. These streets are mainly in the Old Town area where Colonel James Wood and Thomas, Lord Fairfax laid out the earliest streets. Finally, there are about 44 streets that, so far, I have not been able to discern an origin for. This includes streets like Wyck Street, Tower Avenue, Bruce Street, and Robyn Terrace.
We know that many roads have been renamed in the City. At some point, Boscawen Street took on the name Water Street due to the frequent flooding of the street given its alignment with Town Run. Likewise, Cameron Street became known as Market Street because of the old Market House that stood where Rouss City Hall is today. Loudoun Street was renamed Main Street because that was where most of the businesses were located, including merchants, taverns, and services.
In 1926, City Council adopted a resolution to officially rename Boscawen Street as well as Market Street and Main Street back to the names that James Wood and Lord Fairfax had established. Market Street went back to being Cameron Street and Main Street went back to being Loudoun Street. The methodist church at the NW corner of E. Cork Street and S. Cameron Street still bears the name Market Street UMC because of the forming street name.
The are about 150 former street names that I have been able to identify from old records include maps such as those prepared by the Sanborn Insurance company. While renaming can cause property owners along those streets to have to change their addresses, it is not uncommon for communities to rename streets. Winchester is not an exception to that. There are some streets in Winchester that have been renamed multiple times, including segments of Apple Blossom Drive and Jubal Early Drive.