There are
971 mi
from Evansville, IN to Pittsfield, MA
That's the driving distance. It would take 18 hours 51 mins to go from Evansville, Indiana to Pittsfield, Massachusetts.
The flight distance (direct flight from Evansville, IN to Pittsfield, MA) is 815.45 mi.
971 mi = 1,563.10 kms