| Pittsfield to Shelton (Connecticut) | 79.41 mi (127.80 km) |
| Pittsfield to Shelton (Washington) | 2,422.64 mi (3,898.86 km) |
| Pittsfield to Shenandoah (Louisiana) | 1,285.98 mi (2,069.58 km) |
| Pittsfield to Shepherdsville (Kentucky) | 724.43 mi (1,165.86 km) |
| Pittsfield to Sheridan (Wyoming) | 1,681.33 mi (2,705.84 km) |
| Pittsfield to Sherman (Texas) | 1,403.64 mi (2,258.94 km) |
| Pittsfield to Sherrelwood (Colorado) | 1,651.62 mi (2,658.02 km) |
| Pittsfield to Sherwood (Arkansas) | 1,145.57 mi (1,843.61 km) |
| Pittsfield to Sherwood (Oregon) | 2,437.18 mi (3,922.27 km) |
| Pittsfield to Shiloh (Illinois) | 913.79 mi (1,470.60 km) |
| Pittsfield to Shiloh (Ohio) | 598.76 mi (963.61 km) |
| Pittsfield to Shiloh (Pennsylvania) | 250.99 mi (403.93 km) |
| Pittsfield to Shirley (New York) | 116.28 mi (187.14 km) |
| Pittsfield to Shively (Kentucky) | 722.70 mi (1,163.08 km) |
| Pittsfield to Shoreline (Washington) | 2,380.61 mi (3,831.22 km) |
