| Difficult Run to Oswego (Illinois) | 609.73 mi (981.26 km) |
| Difficult Run to Oswego (New York) | 317.44 mi (510.87 km) |
| Difficult Run to Otsego (Minnesota) | 940.80 mi (1,514.08 km) |
| Difficult Run to Ottawa (Illinois) | 629.13 mi (1,012.49 km) |
| Difficult Run to Ottawa (Kansas) | 964.09 mi (1,551.56 km) |
| Difficult Run to Ottumwa (Iowa) | 810.40 mi (1,304.21 km) |
| Difficult Run to Overland (Missouri) | 700.74 mi (1,127.74 km) |
| Difficult Run to Overland Park (Kansas) | 931.06 mi (1,498.39 km) |
| Difficult Run to Overlea (Maryland) | 54.76 mi (88.12 km) |
| Difficult Run to Oviedo (Florida) | 741.12 mi (1,192.71 km) |
| Difficult Run to Owasso (Oklahoma) | 1,026.05 mi (1,651.27 km) |
| Difficult Run to Owatonna (Minnesota) | 894.89 mi (1,440.18 km) |
| Difficult Run to Owensboro (Kentucky) | 535.14 mi (861.23 km) |
| Difficult Run to Owings Mills (Maryland) | 46.13 mi (74.24 km) |
| Difficult Run to Owosso (Michigan) | 454.72 mi (731.80 km) |
