| Pittsfield to Winder (Georgia) | 813.70 mi (1,309.53 km) |
| Pittsfield to Windsor (California) | 2,580.30 mi (4,152.58 km) |
| Pittsfield to Windsor (Colorado) | 1,635.49 mi (2,632.07 km) |
| Pittsfield to Winfield (Kansas) | 1,301.46 mi (2,094.50 km) |
| Pittsfield to Winnetka (Illinois) | 739.79 mi (1,190.58 km) |
| Pittsfield to Winona (Minnesota) | 930.96 mi (1,498.23 km) |
| Pittsfield to Winston-Salem (North Carolina) | 576.29 mi (927.45 km) |
| Pittsfield to Winter Garden (Florida) | 1,068.02 mi (1,718.81 km) |
| Pittsfield to Winter Gardens (California) | 2,450.45 mi (3,943.63 km) |
| Pittsfield to Winter Haven (Florida) | 1,104.17 mi (1,776.99 km) |
| Pittsfield to Winter Park (Florida) | 1,058.33 mi (1,703.22 km) |
| Pittsfield to Winter Springs (Florida) | 1,050.85 mi (1,691.19 km) |
| Pittsfield to Winterville (North Carolina) | 527.26 mi (848.55 km) |
| Pittsfield to Winton (California) | 2,501.04 mi (4,025.04 km) |
| Pittsfield to Wisconsin Rapids (Wisconsin) | 840.58 mi (1,352.78 km) |
