| Pittsfield to Owosso (Michigan) | 554.93 mi (893.08 km) |
| Pittsfield to Oxford (Alabama) | 917.53 mi (1,476.63 km) |
| Pittsfield to Oxford (Mississippi) | 1,040.62 mi (1,674.72 km) |
| Pittsfield to Oxford (Ohio) | 632.05 mi (1,017.19 km) |
| Pittsfield to Oxnard (California) | 2,521.63 mi (4,058.18 km) |
| Pittsfield to Oxon Hill (Maryland) | 319.25 mi (513.78 km) |
| Pittsfield to Ozark (Alabama) | 1,020.28 mi (1,641.98 km) |
| Pittsfield to Ozark (Missouri) | 1,121.01 mi (1,804.10 km) |
| Pittsfield to Pace (Florida) | 1,121.50 mi (1,804.89 km) |
| Pittsfield to Pacific Grove (California) | 2,588.48 mi (4,165.76 km) |
| Pittsfield to Pacifica (California) | 2,588.60 mi (4,165.96 km) |
| Pittsfield to Paducah (Kentucky) | 895.90 mi (1,441.82 km) |
| Pittsfield to Pahrump (Nevada) | 2,299.06 mi (3,699.98 km) |
| Pittsfield to Painesville (Ohio) | 412.76 mi (664.28 km) |
| Pittsfield to Palatine (Illinois) | 755.02 mi (1,215.08 km) |
