| Pittsfield to Romeoville (Illinois) | 762.57 mi (1,227.23 km) |
| Pittsfield to Romulus (Michigan) | 516.05 mi (830.51 km) |
| Pittsfield to Ronkonkoma (New York) | 114.08 mi (183.60 km) |
| Pittsfield to Roosevelt (New York) | 123.57 mi (198.86 km) |
| Pittsfield to Rosamond (California) | 2,451.78 mi (3,945.76 km) |
| Pittsfield to Rosaryville (Maryland) | 315.84 mi (508.29 km) |
| Pittsfield to Roscoe (Illinois) | 801.85 mi (1,290.45 km) |
| Pittsfield to Rose Hill (Virginia) | 323.70 mi (520.95 km) |
| Pittsfield to Roseburg (Oregon) | 2,499.63 mi (4,022.77 km) |
| Pittsfield to Rosedale (California) | 2,486.44 mi (4,001.53 km) |
| Pittsfield to Rosedale (Maryland) | 274.55 mi (441.84 km) |
| Pittsfield to Roselle (Illinois) | 758.38 mi (1,220.49 km) |
| Pittsfield to Roselle (New Jersey) | 134.61 mi (216.63 km) |
| Pittsfield to Roselle Park (New Jersey) | 133.94 mi (215.55 km) |
| Pittsfield to Rosemead (California) | 2,469.64 mi (3,974.50 km) |
