What are the toughest individual Swim/ Bike/ Run events?
What are the toughest/ Longest swims?
Is RAAM the cycling pinnacle?
Badwater?
RAAM has to be one of if not the toughest as it is also a sleep deprivation contest. The Badwater ultra marathon is one of the toughest runs and getting selected is even tougher that getting selected for Hawaii Ironman.
I think it depends on how you define toughest.
RAAM certainly is up there
You could say 24 hour racing on a mountain bike, It’s shorter but guys aren’t pacing themselves anymore, they ride them pretty close to flat out now. At the 2006 worlds, the winner put himself in the hospital for two days.
To just do or race? Big difference.
Race - I say simply the marathon. Period.
Absolutely agree. A standalone flat out Mary where you are at your physical limit the entire way is one of the toughest things in the world to do.
Western States 100 has to be one of the toughest running events in North America
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As someone mentioned, there is a difference between racing and “doing.” Some events are set up where it’s not so much a race against the clock (for most!) as it is an extreme battle of attrition and successfully dealing with fatigue and sleep deprivation.
I think the longest SBR race in U.S. is the triple Ironman in VA
I would think RAAM is probably the toughest cycling event. When you throw in massive sleep deprivation things probably get pretty weird 
For running, I would think Badwater is definitely near/at the top of the list?
any multi-stage adventure race takes the cake.
Badwater? No way. Try this.
O/P mentioned nothing about “racing”, just endurance “events”.
As far as I know, Badwater, RAAM, etc. are all timed …
Belt buckles given out for a reason.
Yeah, I’d put Badwater way up there.
Iditabike in Alaska is in my opinion one of the toughest cycling events. Quit that event and sit down somewhere and/or get lost, and you may actually die/freeze to death.
Herbert
Yes, I forgot about this race. Wild!
Sri Chinmoy foot race in NYC. 3100 miles in 51 days on a .55 mile loop course. You have 51 days to complete so one must average 60+ miles/day. Man there are a lot of freaks out there! I’m all about going long, but still like to try to go fast. Granted “fast” is different in any distance. Slogging along for 51 days is not fast though.
I’d put the Minnesota BtB triathlon in this category. Maybe not near the top, and it is a team rather than solo, but still be a tough go of it.
John
Toughest Single 140.6 distance SBR - Silverman
Toughest Run- Gosh - I would have said Badwater, but that race in NYC Damn!!!
Toughest ride - RAAM (solo)
Is the Subaru Primalquest Adventure Race still going on in Colorado?
Has anyone mentioned climbing Mt. McKinley? Talk about a feat of endurance!
Toughest for me was the first 10k I ever entered (1998 Bolder Boulder, it was the first time I’d moved my body more than a mile on foot intentionally).
After that, everything has gotten easier 
Jason
Atlantic City Around-The-Island Marathon Swim
22.5 miles marathon open water ocean swimming against ocean, inlets and tides.
It is the hardest race in the world. The conditions vary so much…the ocean and the cold water, the tides and the currents, the warm water in the back bay, then the cold water again in the last 400 meters…and the strongest current of the race is at the end where you swim for your life !" 8/10/03, Angela Maurer, Germany
“It is the hardest thing I’ve ever done in my life,” says former winner David Aliva of Blacksburg, Virginia. *** “And it always will be.”***
Primal Quest or Eco Challenge… those that actually “race” each that is.
You beat me too it, this would definitely get my vote. Its also in July when it is hot and humid. And its all on a sidewalk! Ouch!