| Pittsfield to Woodlawn (Virginia) | 326.88 mi (526.07 km) |
| Pittsfield to Woodlyn (Pennsylvania) | 208.28 mi (335.19 km) |
| Pittsfield to Woodmere (Louisiana) | 1,275.44 mi (2,052.63 km) |
| Pittsfield to Woodmere (New York) | 127.60 mi (205.35 km) |
| Pittsfield to Woodridge (Illinois) | 758.44 mi (1,220.59 km) |
| Pittsfield to Woods Cross (Utah) | 1,981.04 mi (3,188.18 km) |
| Pittsfield to Woodstock (Georgia) | 838.26 mi (1,349.04 km) |
| Pittsfield to Woodstock (Illinois) | 773.52 mi (1,244.86 km) |
| Pittsfield to Woodward (Oklahoma) | 1,449.36 mi (2,332.52 km) |
| Pittsfield to Woonsocket (Rhode Island) | 95.34 mi (153.43 km) |
| Pittsfield to Wooster (Ohio) | 461.67 mi (742.98 km) |
| Pittsfield to Worcester (Massachusetts) | 75.21 mi (121.04 km) |
| Pittsfield to World Golf Village (Florida) | 975.93 mi (1,570.61 km) |
| Pittsfield to Worth (Illinois) | 746.25 mi (1,200.98 km) |
| Pittsfield to Worthington (Minnesota) | 1,127.58 mi (1,814.66 km) |
