This geographic advantage isn’t just a recent realization, as Winchester changed hands 72 times during the Civil War. As that might lead one to think, the town sits in the middle of an area of considerable historic interest. The downtown core with its historic buildings is attractive and interesting. The exceptional central historic district could be used as a 19th century or Civil War movie set is occupied by small businesses, artisans and minor entertainment venues. Some sprawl has emerged outside of town, particularly to the south towards the connection I-66 freeway.

The immediate area around Winchester is a flat mix of typical agriculture and orchard land. Low, wooded foothills and mountains of the Blue Ridge and the main Appalachian range are visible to the east and west respectively. The mountains produce a notably mild climate for the region. Summers are warm, mostly calm and humid with periodic rainy spells and thunderstorms. Winters are cold and can be wet, but severe effects of northwesterly cold blasts are moderated by the mountains. Periods of heavy rain or snow may occur with storms moving up off the Atlantic. Spring and especially fall are quite pleasant. First freeze is late October, last is mid April.