| Pittsfield to Stephenville (Texas) | 1,534.85 mi (2,470.11 km) |
| Pittsfield to Sterling (Colorado) | 1,545.17 mi (2,486.71 km) |
| Pittsfield to Sterling (Illinois) | 842.10 mi (1,355.23 km) |
| Pittsfield to Sterling (Virginia) | 322.09 mi (518.35 km) |
| Pittsfield to Sterling Heights (Michigan) | 497.37 mi (800.44 km) |
| Pittsfield to Steubenville (Ohio) | 409.08 mi (658.36 km) |
| Pittsfield to Stevens Point (Wisconsin) | 827.61 mi (1,331.91 km) |
| Pittsfield to Stevenson Ranch (California) | 2,485.40 mi (3,999.86 km) |
| Pittsfield to Stillwater (Minnesota) | 990.61 mi (1,594.24 km) |
| Pittsfield to Stillwater (Oklahoma) | 1,340.84 mi (2,157.87 km) |
| Pittsfield to Stockbridge (Georgia) | 857.15 mi (1,379.45 km) |
| Pittsfield to Stockton (California) | 2,520.08 mi (4,055.67 km) |
| Pittsfield to Stone Ridge (Virginia) | 331.36 mi (533.28 km) |
| Pittsfield to Stonecrest (Georgia) | 845.38 mi (1,360.51 km) |
| Pittsfield to Stony Brook (New York) | 107.01 mi (172.22 km) |
