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CUNY Graduate School and University Center to Winchester, VA buses and trains from $65
Here are some trips other travelers have found on Routefriend.
$65
6h 9m
1 stop
 Amtrak
$100
7h 0m
2 stops
 BoltBus Amtrak
$100
8h 15m
2 stops
 GotoBus Amtrak
$100
8h 55m
2 stops
 CoachUSA Amtrak
$101
9h 45m
2 stops
 GotoBus Amtrak
$146
6h 39m
2 stops
 NJTransit Amtrak