Winchester sits at the junction of I-81 and US Route 50, about 72 miles west of Washington, D.C. The drive from D.C. takes around 90 minutes in normal traffic, less on weekends. From the south, I-81 runs the length of the Shenandoah Valley directly into town.
There is no commercial airport in Winchester. The nearest is Dulles International Airport (IAD), roughly 60 miles to the east. Reagan National (DCA) is about the same distance. Car rental at either airport is the most practical approach for visiting Winchester and the surrounding valley.
Amtrak does not serve Winchester directly. The closest station with regular service is Martinsburg, West Virginia, about 20 miles north, on the Capitol Limited line running between Washington and Chicago. From Martinsburg you'll need a taxi or rideshare into Winchester. Greyhound and FlixBus connect Winchester to Washington and other East Coast cities, with stops on the edge of town.