What was the most extreme or hardcore racing event or obstacle course that you have conducted?

A few years back, and a couple after leaving active duty, I signed up for an "endurance event" sponsored by a local Army unit. Not only was I the only Sailor present...but considerably older than the core of the participants. The rules were thus: 50 miles, 50 lbs or more. There was a uniform inspection before departure.

Now, I "knew" the key here was pacing myself, hydrating, and most importantly...broken in boots. I was in pretty good shape, and felt confident. However, being the only Squid, I didn't want to look like crap in my beat up old sand boots and wore a new pair "hoping" it wouldn't be that big a deal if I took my time. Well...the Soldiers started out RUNNING...and naturally, I couldn't let them show me up like that. I kept up for the first five miles or so before feeling that dreaded "hot spot" or two. By ten miles, I was already fighting the pain...by thirty, after climbing a steep grade, I was literally on my knees.

A 2LT was driving around on a 4x4 as "safety". The first time he came by, I assured him I appreciated his assistance, but intended to finish. The second time he came by, I was still insisting that I would make the finish line if it killed me. The third time, the patient officer said, "Sir, I don't want to insult your drive, but listen...the guys are all back and I've got to stay out here until everyone's safely in-Think it's time you called it Sir."

To make matters worse, once we arrived back at the aid station, I was about (you guessed it) fifty miles from my vehicle. Now the event took place in my hometown...and (wait for it)...my mother still resides there. Guess who's phone number was the only one I had memorized?

That's right..."Mommy" had to come get me...talk about turning fifty shades of embarrassed on that one! LOL

I'm doing Dopey this year. Day 1 - 5k, Day 2 - 10k, day 3, 13.1 mile, Day 4 Marathon. I've got a 50k under my belt and a few "challenge" runs (back to back races).

There's a company that does some great "X Marathons in X days" that I would love to do, but I need the vacation time to rock that out.

200 mile road march completed in 8 days.