| Pittsfield to Hillcrest Heights (Maryland) | 316.26 mi (508.97 km) |
| Pittsfield to Hilliard (Ohio) | 540.23 mi (869.41 km) |
| Pittsfield to Hillsboro (Oregon) | 2,438.91 mi (3,925.05 km) |
| Pittsfield to Hillsborough (California) | 2,584.07 mi (4,158.66 km) |
| Pittsfield to Hillsborough (New Jersey) | 152.46 mi (245.36 km) |
| Pittsfield to Hilo (Hawaii) | 4,903.08 mi (7,890.75 km) |
| Pittsfield to Hilton Head Island (South Carolina) | 819.00 mi (1,318.05 km) |
| Pittsfield to Hinesville (Georgia) | 865.46 mi (1,392.82 km) |
| Pittsfield to Hinsdale (Illinois) | 752.00 mi (1,210.22 km) |
| Pittsfield to Hobart (Indiana) | 721.76 mi (1,161.56 km) |
| Pittsfield to Hobbs (New Mexico) | 1,757.89 mi (2,829.06 km) |
| Pittsfield to Hobe Sound (Florida) | 1,131.08 mi (1,820.30 km) |
| Pittsfield to Hoboken (New Jersey) | 124.40 mi (200.20 km) |
| Pittsfield to Hockessin (Delaware) | 223.28 mi (359.33 km) |
| Pittsfield to Hoffman Estates (Illinois) | 760.75 mi (1,224.30 km) |
