| Pittsfield to Shoreview (Minnesota) | 1,005.56 mi (1,618.29 km) |
| Pittsfield to Shorewood (Illinois) | 769.73 mi (1,238.77 km) |
| Pittsfield to Shorewood (Wisconsin) | 742.18 mi (1,194.43 km) |
| Pittsfield to Short Hills (New Jersey) | 130.56 mi (210.11 km) |
| Pittsfield to Short Pump (Virginia) | 403.61 mi (649.54 km) |
| Pittsfield to Show Low (Arizona) | 2,053.55 mi (3,304.86 km) |
| Pittsfield to Shreveport (Louisiana) | 1,315.53 mi (2,117.13 km) |
| Pittsfield to Sicklerville (New Jersey) | 207.62 mi (334.13 km) |
| Pittsfield to Sidney (Ohio) | 584.44 mi (940.56 km) |
| Pittsfield to Sierra Madre (California) | 2,464.88 mi (3,966.84 km) |
| Pittsfield to Sierra Vista (Arizona) | 2,158.21 mi (3,473.30 km) |
| Pittsfield to Sierra Vista Southeast (Arizona) | 2,157.14 mi (3,471.58 km) |
| Pittsfield to Signal Hill (California) | 2,482.42 mi (3,995.07 km) |
| Pittsfield to Sikeston (Missouri) | 947.65 mi (1,525.10 km) |
| Pittsfield to Siloam Springs (Arkansas) | 1,212.61 mi (1,951.50 km) |
