| Pittsfield to Superior (Colorado) | 1,657.74 mi (2,667.88 km) |
| Pittsfield to Superior (Wisconsin) | 968.90 mi (1,559.30 km) |
| Pittsfield to Surprise (Arizona) | 2,194.95 mi (3,532.43 km) |
| Pittsfield to Susanville (California) | 2,424.79 mi (3,902.32 km) |
| Pittsfield to Sussex (Wisconsin) | 759.05 mi (1,221.58 km) |
| Pittsfield to Suwanee (Georgia) | 823.81 mi (1,325.80 km) |
| Pittsfield to Swansea (Illinois) | 917.34 mi (1,476.32 km) |
| Pittsfield to Sweetwater (Florida) | 1,220.63 mi (1,964.41 km) |
| Pittsfield to Sweetwater (Texas) | 1,631.46 mi (2,625.58 km) |
| Pittsfield to Sycamore (Illinois) | 788.60 mi (1,269.12 km) |
| Pittsfield to Sylacauga (Alabama) | 954.03 mi (1,535.36 km) |
| Pittsfield to Sylvania (Ohio) | 537.92 mi (865.70 km) |
| Pittsfield to Syosset (New York) | 113.72 mi (183.02 km) |
| Pittsfield to Syracuse (New York) | 151.84 mi (244.36 km) |
| Pittsfield to Syracuse (Utah) | 1,984.66 mi (3,194.00 km) |
