| Pittsfield to Oakleaf Plantation (Florida) | 972.43 mi (1,564.98 km) |
| Pittsfield to Oakley (California) | 2,538.96 mi (4,086.06 km) |
| Pittsfield to Oakton (Virginia) | 324.65 mi (522.48 km) |
| Pittsfield to Oakville (Missouri) | 936.75 mi (1,507.55 km) |
| Pittsfield to Oatfield (Oregon) | 2,424.59 mi (3,902.01 km) |
| Pittsfield to Ocala (Florida) | 1,042.22 mi (1,677.29 km) |
| Pittsfield to Ocean Acres (New Jersey) | 194.54 mi (313.08 km) |
| Pittsfield to Ocean City (New Jersey) | 230.86 mi (371.53 km) |
| Pittsfield to Ocean Pines (Maryland) | 297.99 mi (479.57 km) |
| Pittsfield to Ocean Pointe (Hawaii) | 4,978.87 mi (8,012.72 km) |
| Pittsfield to Ocean Springs (Mississippi) | 1,195.20 mi (1,923.48 km) |
| Pittsfield to Oceanside (California) | 2,457.20 mi (3,954.48 km) |
| Pittsfield to Oceanside (New York) | 127.17 mi (204.66 km) |
| Pittsfield to Ocoee (Florida) | 1,064.10 mi (1,712.50 km) |
| Pittsfield to Oconomowoc (Wisconsin) | 772.85 mi (1,243.78 km) |
