| Pittsfield to Wichita (Kansas) | 1,310.32 mi (2,108.75 km) |
| Pittsfield to Wichita Falls (Texas) | 1,486.70 mi (2,392.61 km) |
| Pittsfield to Wickliffe (Ohio) | 425.13 mi (684.18 km) |
| Pittsfield to Wildomar (California) | 2,441.97 mi (3,929.97 km) |
| Pittsfield to Wildwood (Florida) | 1,063.61 mi (1,711.71 km) |
| Pittsfield to Wildwood (Missouri) | 950.81 mi (1,530.18 km) |
| Pittsfield to Wilkes-Barre (Pennsylvania) | 158.26 mi (254.70 km) |
| Pittsfield to Wilkinsburg (Pennsylvania) | 369.36 mi (594.43 km) |
| Pittsfield to Williamsburg (Virginia) | 401.95 mi (646.87 km) |
| Pittsfield to Williamsport (Pennsylvania) | 211.62 mi (340.57 km) |
| Pittsfield to Williamstown (New Jersey) | 210.91 mi (339.43 km) |
| Pittsfield to Willimantic (Connecticut) | 73.96 mi (119.03 km) |
| Pittsfield to Williston (North Dakota) | 1,517.04 mi (2,441.44 km) |
| Pittsfield to Willmar (Minnesota) | 1,099.26 mi (1,769.09 km) |
| Pittsfield to Willoughby (Ohio) | 421.57 mi (678.45 km) |
