| Pittsfield to Holbrook (New York) | 114.93 mi (184.96 km) |
| Pittsfield to Holiday (Florida) | 1,119.52 mi (1,801.69 km) |
| Pittsfield to Holiday City-Berkeley (New Jersey) | 179.85 mi (289.44 km) |
| Pittsfield to Holladay (Utah) | 1,980.44 mi (3,187.21 km) |
| Pittsfield to Holland (Michigan) | 652.56 mi (1,050.20 km) |
| Pittsfield to Hollins (Virginia) | 500.12 mi (804.87 km) |
| Pittsfield to Hollister (California) | 2,555.15 mi (4,112.11 km) |
| Pittsfield to Holly Hill (Florida) | 1,010.26 mi (1,625.86 km) |
| Pittsfield to Holly Springs (Georgia) | 834.01 mi (1,342.20 km) |
| Pittsfield to Holly Springs (North Carolina) | 556.75 mi (896.00 km) |
| Pittsfield to Hollywood (Florida) | 1,200.22 mi (1,931.57 km) |
| Pittsfield to Holmen (Wisconsin) | 910.90 mi (1,465.95 km) |
| Pittsfield to Holt (Michigan) | 573.42 mi (922.82 km) |
| Pittsfield to Holtsville (New York) | 113.81 mi (183.16 km) |
| Pittsfield to Holyoke (Massachusetts) | 35.69 mi (57.44 km) |
