| Pittsfield to University Place (Washington) | 2,396.60 mi (3,856.95 km) |
| Pittsfield to Upland (California) | 2,446.60 mi (3,937.42 km) |
| Pittsfield to Upper Arlington (Ohio) | 536.12 mi (862.81 km) |
| Pittsfield to Upper Grand Lagoon (Florida) | 1,094.31 mi (1,761.12 km) |
| Pittsfield to Upper Montclair (New Jersey) | 121.26 mi (195.16 km) |
| Pittsfield to Urbana (Illinois) | 791.13 mi (1,273.19 km) |
| Pittsfield to Urbana (Maryland) | 303.33 mi (488.16 km) |
| Pittsfield to Urbana (Ohio) | 567.97 mi (914.05 km) |
| Pittsfield to Urbandale (Iowa) | 1,051.84 mi (1,692.77 km) |
| Pittsfield to Utica (New York) | 109.18 mi (175.71 km) |
| Pittsfield to Uvalde (Texas) | 1,733.17 mi (2,789.27 km) |
| Pittsfield to Vacaville (California) | 2,542.95 mi (4,092.49 km) |
| Pittsfield to Vadnais Heights (Minnesota) | 1,002.47 mi (1,613.33 km) |
| Pittsfield to Vail (Arizona) | 2,161.19 mi (3,478.10 km) |
| Pittsfield to Valdosta (Georgia) | 973.58 mi (1,566.82 km) |
