| Pittsfield to Worthington (Ohio) | 531.99 mi (856.16 km) |
| Pittsfield to Wright (Florida) | 1,111.37 mi (1,788.57 km) |
| Pittsfield to Wyandanch (New York) | 117.72 mi (189.46 km) |
| Pittsfield to Wyandotte (Michigan) | 505.42 mi (813.39 km) |
| Pittsfield to Wylie (Texas) | 1,420.93 mi (2,286.77 km) |
| Pittsfield to Wyndham (Virginia) | 401.21 mi (645.68 km) |
| Pittsfield to Wyoming (Michigan) | 632.43 mi (1,017.79 km) |
| Pittsfield to Wyomissing (Pennsylvania) | 202.92 mi (326.57 km) |
| Pittsfield to Xenia (Ohio) | 587.86 mi (946.07 km) |
| Pittsfield to Yakima (Washington) | 2,311.83 mi (3,720.53 km) |
| Pittsfield to Yankton (South Dakota) | 1,222.12 mi (1,966.81 km) |
| Pittsfield to Yauco (Puerto Rico) | 1,728.46 mi (2,781.68 km) |
| Pittsfield to Yazoo City (Mississippi) | 1,144.80 mi (1,842.38 km) |
| Pittsfield to Yeadon (Pennsylvania) | 202.53 mi (325.95 km) |
| Pittsfield to Yelm (Washington) | 2,403.88 mi (3,868.67 km) |
