| Pittsfield to Smolyan | 4,711.39 mi (7,582.25 km) |
| Pittsfield to Sofia | 4,608.72 mi (7,417.01 km) |
| Pittsfield to Sopot | 4,668.11 mi (7,512.60 km) |
| Pittsfield to Sozopol | 4,795.64 mi (7,717.83 km) |
| Pittsfield to Sredets | 4,778.77 mi (7,690.69 km) |
| Pittsfield to Stamboliyski | 4,681.25 mi (7,533.75 km) |
| Pittsfield to Stara Zagora | 4,713.42 mi (7,585.52 km) |
| Pittsfield to Svilengrad | 4,764.17 mi (7,667.19 km) |
| Pittsfield to Svishtov | 4,651.13 mi (7,485.27 km) |
| Pittsfield to Targovishte | 4,715.45 mi (7,588.78 km) |
| Pittsfield to Teteven | 4,637.45 mi (7,463.25 km) |
| Pittsfield to Troyan | 4,656.91 mi (7,494.57 km) |
| Pittsfield to Tryavna | 4,688.92 mi (7,546.08 km) |
| Pittsfield to Tutrakan | 4,682.45 mi (7,535.67 km) |
| Pittsfield to Varna | 4,769.18 mi (7,675.25 km) |
