There are
1,998 mi
from Upland, CA to Owensboro, KY
That's the driving distance. It would take 1 day 11 hours to go from Upland, California to Owensboro, Kentucky.
The flight distance (direct flight from Upland, CA to Owensboro, KY) is 1,719.35 mi.
1,998 mi = 1.61 kms