There are
2,948 mi
from Gresham, OR to Pittsfield, MA
That's the driving distance. It would take 2 days 4 hours to go from Gresham, Oregon to Pittsfield, Massachusetts.
The flight distance (direct flight from Gresham, OR to Pittsfield, MA) is 2,416.24 mi.
2,948 mi = 3.22 kms