| Pittsfield to Silver Firs (Washington) | 2,370.54 mi (3,815.02 km) |
| Pittsfield to Silver Spring (Maryland) | 309.04 mi (497.35 km) |
| Pittsfield to Silver Springs Shores (Florida) | 1,042.72 mi (1,678.09 km) |
| Pittsfield to Silverdale (Washington) | 2,397.26 mi (3,858.02 km) |
| Pittsfield to Silverton (Oregon) | 2,440.06 mi (3,926.90 km) |
| Pittsfield to Simi Valley (California) | 2,497.42 mi (4,019.21 km) |
| Pittsfield to Simpsonville (South Carolina) | 720.80 mi (1,160.02 km) |
| Pittsfield to Sioux City (Iowa) | 1,175.06 mi (1,891.08 km) |
| Pittsfield to Sioux Falls (South Dakota) | 1,184.53 mi (1,906.31 km) |
| Pittsfield to Skokie (Illinois) | 740.27 mi (1,191.35 km) |
| Pittsfield to Sleepy Hollow (New York) | 98.99 mi (159.30 km) |
| Pittsfield to Slidell (Louisiana) | 1,241.27 mi (1,997.63 km) |
| Pittsfield to Smithfield (North Carolina) | 551.58 mi (887.68 km) |
| Pittsfield to Smithfield (Utah) | 1,959.01 mi (3,152.73 km) |
| Pittsfield to Smithville (Missouri) | 1,129.51 mi (1,817.77 km) |
