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Winchester, VA to Sojourner-Douglass College buses and trains from $32
Here are some trips other travelers have found on Routefriend.
$32
4h 43m
1 stop
 Amtrak
$82
8h 45m
2 stops
 Amtrak GotoBus
$185
12h 0m
2 stops
 Amtrak GotoBus