There are
2,288 mi
from San Mateo, CA to Madisonville, KY
That's the driving distance. It would take 1 day 16 hours to go from San Mateo, California to Madisonville, Kentucky.
The flight distance (direct flight from San Mateo, CA to Madisonville, KY) is 1,899.41 mi.
2,288 mi = 3.22 kms