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| Month | Race Name | Events | Location | Near | |
| May | Ganaraska Trail Runs | 50 km, 25 km, 12.5 km | ON, Canada | Orillia | |
| May | Ice Age Trail 50 | 50 mi, 50 km | WI, United States | La Grange | |
| May | XTERRA Malibu Creek Trail Challenge Scramble | 14 mi, 4 mi | CA, United States | Calabasas | |
| May | Spring Salmon Run | 10 km | CA, United States | Nevada City | |
| May | Long Island Greenbelt Trail 50K and 25K Runs | 50 km, 25 km | NY, United States | Plainview | |
| May | Dandelion Run | 10 km, 5 km | OH, United States | Dover | |
| May | McDonald Forest Cross Country Race | 50 km, 15 km | OR, United States | Corvallis | |
| May | Sky Mesa Pass Trail Marathon | 26.2 mi | CO, United States | Grand Junction |
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