There are
2,994 mi
from Redwood City, CA to Pittsfield, MA
That's the driving distance. It would take 2 days 5 hours to go from Redwood City, California to Pittsfield, Massachusetts.
The flight distance (direct flight from Redwood City, CA to Pittsfield, MA) is 2,580.65 mi.
2,994 mi = 4,818.99 kms