| Pittsfield to Rancho Cordova (California) | 2,501.54 mi (4,025.85 km) |
| Pittsfield to Rancho Cucamonga (California) | 2,441.61 mi (3,929.39 km) |
| Pittsfield to Rancho Mirage (California) | 2,394.93 mi (3,854.27 km) |
| Pittsfield to Rancho Palos Verdes (California) | 2,493.89 mi (4,013.53 km) |
| Pittsfield to Rancho San Diego (California) | 2,452.58 mi (3,947.05 km) |
| Pittsfield to Rancho Santa Margarita (California) | 2,458.87 mi (3,957.16 km) |
| Pittsfield to Randallstown (Maryland) | 281.85 mi (453.60 km) |
| Pittsfield to Rantoul (Illinois) | 785.27 mi (1,263.76 km) |
| Pittsfield to Rapid City (South Dakota) | 1,503.28 mi (2,419.29 km) |
| Pittsfield to Ravenna (Ohio) | 420.46 mi (676.67 km) |
| Pittsfield to Raymondville (Texas) | 1,768.79 mi (2,846.59 km) |
| Pittsfield to Raymore (Missouri) | 1,136.60 mi (1,829.17 km) |
| Pittsfield to Raytown (Missouri) | 1,132.52 mi (1,822.62 km) |
| Pittsfield to Reading (Ohio) | 624.56 mi (1,005.13 km) |
| Pittsfield to Reading (Pennsylvania) | 200.94 mi (323.38 km) |
