I’ve wanted to qualify for UTMB but have not had access to qualifying events for the last couple of years but have found something possibly event more bonkers than that: http://www.sportcommunication.info/TMB/
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Powerman Zofingen long course duathlon (Switzerland)
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My wife just did Coast to Coast in NZ and said it was way harder than IM. It usually takes 3.5-5hrs longer than IM.
American Zofingen long course duathlon.
I did the 273Km Liege Bastogne Liege challenge last year. Set personal records for longest ride (time and distance), most climbing, miles ridden in the rain, and most Belgium waffles eaten on a ride.
STP ridden continuous…with others faster than me. SilverMan. Big Horn 100. The Rut50k
Silverman Full 2005-2011, Savageman 70.0 day after the 30.0 , 2nd day of the Hoodoo 300 stage ride (1st day was ez compared to the climbing the 2nd day) , the Markleeville Death ride/Tour of the California Alps when it was 150miles
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Norseman 2013, the year we had to walk down 3 miles on the rocky trail back to the car since the elevator was taken out by lightening. It was perfect 
The first day of a two-day hangover following one of my best friend’s bachelor weekend.
I know we’ve got some other LoToJa riders in the forum: 203 miles on the road bike, some climbing, usually around 10 hours for me. About halfway through a jog actually starts to sound nice!!!
-Eric
What did you think of LBL? I’ve done the RVV and Paris-Roubaix sportives but for some reason (most likely my own ignorance) the LBL route has never quite inspired me or grabbed my attention enough to sign up.
Would you recommend it?
North Face Endurance Challenge Wisconsin 50 Miler
Crossed Puerto Rico running from North to South, total of 50 miles. SO HOT!
This year doing the Superior 100 in Northern Minnesota.
Canadian Death Race. 125km of knee punishing running.
The double hump over Mt Mother at Camp Pendleton
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Rapha Prestige in LA last year.
127 miles and 13.5k in upness.
Solid mix between road and dirt. About 9 hours in the saddle. That was harder than IM for me. I would do it again for sure though.
Jake
Hardest to easiest - 100 mile trail run. Self-supported ultraman. Self-supported Ironmans. Swimming 22 miles across Lake Tahoe south to north. Those things make a WTC ironman seem like a catered birthday party. (cheering and constant variety of food). All are good, just different.
Rim2Rim2Rim or back in the day Central Jersey Bike Club did 200 Miles top of New Jersey to Cape May in a day. I think it was like 9-10 hours as a 16 year old, crushed me… O and every bike race I did in Europe on cobbles… but Rim2Rim2Rim was the hardest but also the coolest
What did you think of LBL? I’ve done the RVV and Paris-Roubaix sportives but for some reason (most likely my own ignorance) the LBL route has never quite inspired me or grabbed my attention enough to sign up.
Would you recommend it?
Its never really been a lifelong goal of mine or anything I had the opportunity to do it and am glad I did. I would recommend it but I havent ridden too many other spring classics courses to compare it too. I rode parts of Amstel Gold and Fleche Wallone which I also enjoyed but I didnt ride the whole course so its tough to compare them.
Last year I decided I wanted to go on a cycling vacation and signed up for a tour in Belgium during the spring classics. We rode the Amstel Gold, Fleche Wallone, and LBL courses the day before the pro races. I held back during the Amstel and Fleche Wallone doing the 60-80 mile options. I was feeling good at the end of the week and decided to go big and complete the whole LBL course.
We had great weather all week it was in the 70’s and sunny. But the night before the LBL sportive the rain came in. I grinded for almost 13 hours in the rain and almost ran out of brake pads in the rear. Honestly I wouldn’t change a thing (other than starting the ride with fresh brake pads). I got to end my vacation with an epic all day rain ride. Half of the tour group didnt ride that day 3 of us did the entire thing, and 2 others rode the shorter route.
Riding through Liege isnt all that great, but riding through the Ardennes forest was nice. I wasn’t a huge road racing fan before the trip. I know have a much better appreciation for how good the pros are, and am a much bigger fan of the sport after having experienced it up close. I’m hoping in the future to tackle Paris Roubaix and other rides.
Aiming to do something not dissimilar next summer, the Monx Ventoux Bicinglette challenge. Six ascents of Ventoux in 24 hours, from 3 different sides, 8800 vertical metres. http://www.clubcinglesventoux.org/en/rules.html
Other than IM, the hardest day I’ve done to date was doing the South Downs Way which is a 100 mile offroad route. ~3500 vertical metres, but some quite tricky terrain (rained a bit when we did it).
Another one that ranked up there but was over 48 hours was doing the 4 peaks, highest peaks in England, Scotland, Wales, Ireland. About 4500m vertical, we were only actually on the hills for about 8 hours, but sitting in a car between peaks and then a ferry across to Ireland was absolutely perfect for letting the legs seize up! My quads and calves were definitely more shot after those 2 days than anything else I’ve ever done. Took about 3 days before I could negotiate a flight of stairs without crabbing up them sideways while holding onto the rail.
Ride Across Indiana (RAIN) bicycle ride. 163 miles in one day. I was very happy to get off my bike and never ride again.