| Pittsfield to Yonkers (New York) | 108.60 mi (174.78 km) |
| Pittsfield to Yorba Linda (California) | 2,459.47 mi (3,958.14 km) |
| Pittsfield to York (Pennsylvania) | 249.10 mi (400.88 km) |
| Pittsfield to Yorktown (Indiana) | 654.18 mi (1,052.80 km) |
| Pittsfield to Yorkville (Illinois) | 780.19 mi (1,255.59 km) |
| Pittsfield to Youngstown (Ohio) | 391.73 mi (630.43 km) |
| Pittsfield to Youngsville (Louisiana) | 1,342.94 mi (2,161.26 km) |
| Pittsfield to Ypsilanti (Michigan) | 528.91 mi (851.20 km) |
| Pittsfield to Yuba City (California) | 2,506.59 mi (4,033.97 km) |
| Pittsfield to Yucaipa (California) | 2,417.77 mi (3,891.03 km) |
| Pittsfield to Yucca Valley (California) | 2,383.28 mi (3,835.52 km) |
| Pittsfield to Yukon (Oklahoma) | 1,394.41 mi (2,244.09 km) |
| Pittsfield to Yulee (Florida) | 936.54 mi (1,507.22 km) |
| Pittsfield to Yuma (Arizona) | 2,337.24 mi (3,761.43 km) |
| Pittsfield to Zachary (Louisiana) | 1,280.01 mi (2,059.97 km) |
