| Pittsfield to Hickory Hills (Illinois) | 747.71 mi (1,203.33 km) |
| Pittsfield to Hicksville (New York) | 117.42 mi (188.98 km) |
| Pittsfield to Hidalgo (Texas) | 1,807.28 mi (2,908.54 km) |
| Pittsfield to High Point (North Carolina) | 573.31 mi (922.66 km) |
| Pittsfield to Highland (California) | 2,421.55 mi (3,897.12 km) |
| Pittsfield to Highland (Illinois) | 896.67 mi (1,443.05 km) |
| Pittsfield to Highland (Indiana) | 730.84 mi (1,176.17 km) |
| Pittsfield to Highland (Utah) | 1,983.70 mi (3,192.45 km) |
| Pittsfield to Highland City (Florida) | 1,111.52 mi (1,788.82 km) |
| Pittsfield to Highland Park (Illinois) | 742.67 mi (1,195.22 km) |
| Pittsfield to Highland Park (New Jersey) | 147.74 mi (237.76 km) |
| Pittsfield to Highland Springs (Virginia) | 401.11 mi (645.52 km) |
| Pittsfield to Highland Village (Texas) | 1,445.15 mi (2,325.74 km) |
| Pittsfield to Highlands Ranch (Colorado) | 1,656.06 mi (2,665.18 km) |
| Pittsfield to Hillcrest (California) | 2,474.11 mi (3,981.70 km) |
