| Pittsfield to Olympia (Washington) | 2,415.00 mi (3,886.57 km) |
| Pittsfield to Olympia Heights (Florida) | 1,223.53 mi (1,969.07 km) |
| Pittsfield to Omaha (Nebraska) | 1,172.27 mi (1,886.58 km) |
| Pittsfield to On Top of the World Designated Place (Florida) | 1,050.30 mi (1,690.29 km) |
| Pittsfield to Onalaska (Wisconsin) | 907.99 mi (1,461.28 km) |
| Pittsfield to Oneida (New York) | 129.25 mi (208.01 km) |
| Pittsfield to Oneonta (New York) | 92.07 mi (148.17 km) |
| Pittsfield to Ontario (California) | 2,446.32 mi (3,936.96 km) |
| Pittsfield to Ontario (Oregon) | 2,177.13 mi (3,503.75 km) |
| Pittsfield to Opa-locka (Florida) | 1,210.38 mi (1,947.93 km) |
| Pittsfield to Opelika (Alabama) | 945.76 mi (1,522.05 km) |
| Pittsfield to Opelousas (Louisiana) | 1,325.96 mi (2,133.92 km) |
| Pittsfield to Orange (California) | 2,464.74 mi (3,966.62 km) |
| Pittsfield to Orange (Texas) | 1,418.13 mi (2,282.25 km) |
| Pittsfield to Orange City (Florida) | 1,035.67 mi (1,666.75 km) |
