| Pittsfield to Rosemont (California) | 2,507.36 mi (4,035.20 km) |
| Pittsfield to Rosemount (Minnesota) | 1,001.03 mi (1,611.00 km) |
| Pittsfield to Rosenberg (Texas) | 1,536.59 mi (2,472.91 km) |
| Pittsfield to Roseville (California) | 2,499.87 mi (4,023.15 km) |
| Pittsfield to Roseville (Michigan) | 492.83 mi (793.14 km) |
| Pittsfield to Roseville (Minnesota) | 1,006.20 mi (1,619.32 km) |
| Pittsfield to Rossmoor (California) | 2,478.40 mi (3,988.60 km) |
| Pittsfield to Rossville (Maryland) | 271.84 mi (437.48 km) |
| Pittsfield to Roswell (Georgia) | 835.32 mi (1,344.31 km) |
| Pittsfield to Roswell (New Mexico) | 1,803.88 mi (2,903.07 km) |
| Pittsfield to Round Lake (Illinois) | 756.55 mi (1,217.54 km) |
| Pittsfield to Round Lake Beach (Illinois) | 755.05 mi (1,215.14 km) |
| Pittsfield to Round Rock (Texas) | 1,577.65 mi (2,538.98 km) |
| Pittsfield to Rowland Heights (California) | 2,462.96 mi (3,963.76 km) |
| Pittsfield to Rowlett (Texas) | 1,427.18 mi (2,296.82 km) |
