| Pittsfield to Odenton (Maryland) | 294.91 mi (474.61 km) |
| Pittsfield to Odessa (Texas) | 1,748.62 mi (2,814.13 km) |
| Pittsfield to Ogden (Utah) | 1,976.92 mi (3,181.55 km) |
| Pittsfield to Oildale (California) | 2,476.32 mi (3,985.25 km) |
| Pittsfield to Ojus (Florida) | 1,204.91 mi (1,939.11 km) |
| Pittsfield to Okemos (Michigan) | 567.29 mi (912.96 km) |
| Pittsfield to Oklahoma City (Oklahoma) | 1,383.62 mi (2,226.71 km) |
| Pittsfield to Okmulgee (Oklahoma) | 1,304.05 mi (2,098.66 km) |
| Pittsfield to Olathe (Kansas) | 1,153.11 mi (1,855.75 km) |
| Pittsfield to Old Jamestown (Missouri) | 924.93 mi (1,488.52 km) |
| Pittsfield to Oldsmar (Florida) | 1,126.05 mi (1,812.21 km) |
| Pittsfield to Olean (New York) | 265.62 mi (427.47 km) |
| Pittsfield to Olive Branch (Mississippi) | 1,030.59 mi (1,658.57 km) |
| Pittsfield to Olivehurst (California) | 2,503.92 mi (4,029.66 km) |
| Pittsfield to Olney (Maryland) | 303.05 mi (487.72 km) |
