| Pittsfield to Savannah (Georgia) | 840.81 mi (1,353.15 km) |
| Pittsfield to Sayreville (New Jersey) | 147.85 mi (237.95 km) |
| Pittsfield to Sayville (New York) | 118.08 mi (190.03 km) |
| Pittsfield to Scaggsville (Maryland) | 296.98 mi (477.94 km) |
| Pittsfield to Scarsdale (New York) | 104.44 mi (168.08 km) |
| Pittsfield to Schaumburg (Illinois) | 757.82 mi (1,219.60 km) |
| Pittsfield to Schenectady (New York) | 41.68 mi (67.08 km) |
| Pittsfield to Schererville (Indiana) | 730.82 mi (1,176.15 km) |
| Pittsfield to Schertz (Texas) | 1,646.80 mi (2,650.27 km) |
| Pittsfield to Schiller Park (Illinois) | 747.54 mi (1,203.04 km) |
| Pittsfield to Schofield Barracks (Hawaii) | 4,972.65 mi (8,002.70 km) |
| Pittsfield to Scotchtown (New York) | 88.15 mi (141.86 km) |
| Pittsfield to Scottdale (Georgia) | 844.43 mi (1,358.98 km) |
| Pittsfield to Scotts Valley (California) | 2,580.48 mi (4,152.89 km) |
| Pittsfield to Scottsbluff (Nebraska) | 1,549.21 mi (2,493.21 km) |
