| Middleburg to Oswego (Illinois) | 880.19 mi (1,416.52 km) |
| Middleburg to Oswego (New York) | 972.45 mi (1,565.00 km) |
| Middleburg to Otsego (Minnesota) | 1,228.36 mi (1,976.85 km) |
| Middleburg to Ottawa (Illinois) | 871.67 mi (1,402.81 km) |
| Middleburg to Ottawa (Kansas) | 962.74 mi (1,549.38 km) |
| Middleburg to Ottumwa (Iowa) | 959.73 mi (1,544.53 km) |
| Middleburg to Overland (Missouri) | 767.39 mi (1,235.00 km) |
| Middleburg to Overland Park (Kansas) | 948.68 mi (1,526.75 km) |
| Middleburg to Overlea (Maryland) | 712.12 mi (1,146.05 km) |
| Middleburg to Oviedo (Florida) | 105.36 mi (169.56 km) |
| Middleburg to Owasso (Oklahoma) | 912.35 mi (1,468.28 km) |
| Middleburg to Owatonna (Minnesota) | 1,151.32 mi (1,852.87 km) |
| Middleburg to Owensboro (Kentucky) | 610.51 mi (982.51 km) |
| Middleburg to Owings Mills (Maryland) | 708.57 mi (1,140.33 km) |
| Middleburg to Owosso (Michigan) | 903.21 mi (1,453.57 km) |
