Guide
The genuinely brutal ones
No sugar-coating: these are the hard ones. Big climbing, long distances, or both. If you want a race that hurts and means something, start here — but respect the cutoffs.
UltraAugust 2026
Leadville 100 Run
Leadville, US · Ultra
Lottery
TrailAugust 2026
CCC
Courmayeur, IT · Ultra
Lottery
TriathlonSeptember 2026
Ironman Wisconsin
Madison, US · 140.6
Open registration
TrailSeptember 2026
Pikes Peak Marathon
Manitou Springs, US · Marathon
Open registration
TriathlonOctober 2026
Ironman Worlds (Kona)
Kailua-Kona, US · 140.6
Qualifier
GravelOctober 2026
La Ruta
Jacó to Turrialba, CR · Stage race
Open registration
UltraFebruary 2027
Coastal Challenge (TCC)
Quepos to Drake Bay, CR · Stage race · Ultra
Open registration
UltraApril 2027
Two Oceans
Cape Town, ZA · Ultra · Half marathon
Open registration
CyclingApril 2027
Sea Otter Classic
Monterey, US · Gran fondo · Gran fondo
Open registration
TriathlonJune 2027
Honu 70.3
Kohala Coast, US · 70.3
Open registration
GravelJune 2027
Unbound Gravel
Emporia, US · Gravel
Lottery
UltraJune 2027
Comrades
Durban, ZA · Ultra
Open registration