| Pittsfield to Storm Lake (Iowa) | 1,113.50 mi (1,792.01 km) |
| Pittsfield to Storrs (Connecticut) | 68.19 mi (109.74 km) |
| Pittsfield to Stoughton (Wisconsin) | 810.11 mi (1,303.75 km) |
| Pittsfield to Stow (Ohio) | 429.86 mi (691.80 km) |
| Pittsfield to Streamwood (Illinois) | 762.70 mi (1,227.45 km) |
| Pittsfield to Streator (Illinois) | 806.15 mi (1,297.37 km) |
| Pittsfield to Streetsboro (Ohio) | 424.31 mi (682.86 km) |
| Pittsfield to Strongsville (Ohio) | 447.65 mi (720.43 km) |
| Pittsfield to Stuart (Florida) | 1,125.01 mi (1,810.52 km) |
| Pittsfield to Stuarts Draft (Virginia) | 431.76 mi (694.84 km) |
| Pittsfield to Sturgis (Michigan) | 624.12 mi (1,004.43 km) |
| Pittsfield to Suamico (Wisconsin) | 755.68 mi (1,216.14 km) |
| Pittsfield to Sudley (Virginia) | 336.70 mi (541.87 km) |
| Pittsfield to Suffern (New York) | 103.00 mi (165.76 km) |
| Pittsfield to Suffolk (Virginia) | 436.45 mi (702.40 km) |
