| Gloucester to Winder (Georgia) | 4,073.83 mi (6,556.19 km) |
| Gloucester to Windsor (California) | 5,240.63 mi (8,433.98 km) |
| Gloucester to Windsor (Colorado) | 4,557.21 mi (7,334.12 km) |
| Gloucester to Winfield (Kansas) | 4,432.21 mi (7,132.95 km) |
| Gloucester to Winnetka (Illinois) | 3,849.32 mi (6,194.88 km) |
| Gloucester to Winona (Minnesota) | 3,906.58 mi (6,287.04 km) |
| Gloucester to Winston-Salem (North Carolina) | 3,831.54 mi (6,166.27 km) |
| Gloucester to Winter Garden (Florida) | 4,254.23 mi (6,846.52 km) |
| Gloucester to Winter Gardens (California) | 5,381.43 mi (8,660.58 km) |
| Gloucester to Winter Haven (Florida) | 4,285.18 mi (6,896.33 km) |
| Gloucester to Winter Park (Florida) | 4,240.81 mi (6,824.93 km) |
| Gloucester to Winter Springs (Florida) | 4,233.22 mi (6,812.71 km) |
| Gloucester to Winterville (North Carolina) | 3,740.60 mi (6,019.91 km) |
| Gloucester to Winton (California) | 5,240.96 mi (8,434.51 km) |
| Gloucester to Wisconsin Rapids (Wisconsin) | 3,822.85 mi (6,152.29 km) |
