| Pittsfield to Oskaloosa (Iowa) | 998.12 mi (1,606.32 km) |
| Pittsfield to Oswego (Illinois) | 774.11 mi (1,245.81 km) |
| Pittsfield to Oswego (New York) | 177.80 mi (286.15 km) |
| Pittsfield to Otsego (Minnesota) | 1,029.87 mi (1,657.41 km) |
| Pittsfield to Ottawa (Illinois) | 802.88 mi (1,292.11 km) |
| Pittsfield to Ottawa (Kansas) | 1,182.21 mi (1,902.58 km) |
| Pittsfield to Ottumwa (Iowa) | 990.59 mi (1,594.20 km) |
| Pittsfield to Overland (Missouri) | 932.74 mi (1,501.10 km) |
| Pittsfield to Overland Park (Kansas) | 1,146.27 mi (1,844.74 km) |
| Pittsfield to Overlea (Maryland) | 272.78 mi (438.99 km) |
| Pittsfield to Oviedo (Florida) | 1,050.86 mi (1,691.19 km) |
| Pittsfield to Owasso (Oklahoma) | 1,273.95 mi (2,050.23 km) |
| Pittsfield to Owatonna (Minnesota) | 1,008.54 mi (1,623.08 km) |
| Pittsfield to Owensboro (Kentucky) | 799.64 mi (1,286.89 km) |
| Pittsfield to Owings Mills (Maryland) | 279.40 mi (449.64 km) |
