| Pittsfield to Orangeburg (South Carolina) | 744.13 mi (1,197.56 km) |
| Pittsfield to Orangevale (California) | 2,497.02 mi (4,018.56 km) |
| Pittsfield to Orchards (Washington) | 2,417.31 mi (3,890.28 km) |
| Pittsfield to Orcutt (California) | 2,563.95 mi (4,126.27 km) |
| Pittsfield to Oregon (Ohio) | 524.44 mi (844.01 km) |
| Pittsfield to Oregon (Wisconsin) | 818.53 mi (1,317.29 km) |
| Pittsfield to Oregon City (Oregon) | 2,425.64 mi (3,903.69 km) |
| Pittsfield to Orem (Utah) | 1,981.46 mi (3,188.85 km) |
| Pittsfield to Orinda (California) | 2,566.26 mi (4,130.00 km) |
| Pittsfield to Orland Park (Illinois) | 750.71 mi (1,208.16 km) |
| Pittsfield to Orlando (Florida) | 1,065.89 mi (1,715.39 km) |
| Pittsfield to Ormond Beach (Florida) | 1,008.13 mi (1,622.43 km) |
| Pittsfield to Oro Valley (Arizona) | 2,161.76 mi (3,479.02 km) |
| Pittsfield to Oroville (California) | 2,493.84 mi (4,013.45 km) |
| Pittsfield to Oshkosh (Wisconsin) | 776.67 mi (1,249.93 km) |
