Nachoman

Haleakala, one or two fast paced century rides, or perhaps a 40 mile ride in palm springs in 108 degree heat.
All three of them I had tunnel vision and was seeing stars.

noglider 

I can't possibly remember enough rides to rate and rank them against each other. A couple of summers ago, I did a solo century ride which was actually 96 miles. I had various challenges.

I didn't want to use turn-by-turn navigation, so I made a route with google maps the night before. But I didn't have a printer, so I wrote them out by hand. I lost one of my cue sheets, so I did use turn by turn for a few periods necessitated also by getting lost.

My rear derailleur (9 speeds) failed so I jury rigged it into a middle cog and had a three speed bike after about mile 35. Then I hit a big hill called Hosner Mountain (in Duchess County, NY). I made it up without stopping. It involved pedalling really slowly, and I think balance was my savior, not strength. It was almost like track standing.

I wasn't in proper shape, so the toll on my back and shoulders was tough. By the time I got to my destination, it was hard to pedal, and after getting off the bike, it was hard to walk or do anything. But I made it. Now I'm doing a lot of exercise, building up my upper body and getting more limber. I'm also doing more miles per year. I expect to do a lot better this year.

noglider 

I'm glad to hear Hillier Than Thou is still running. Why did I think it was no longer? I'm considering entering it now.

ajemm

My hardest to date would be Diabolical Double's baby brother, Masochistic Metric. Only 8,000 ft. of climbing. The worst cramping I've ever experienced. I had to walk a couple times and actually toppled over on the limestone climb because my legs hurt so bad. I can't wait to do it again this year. This time with a compact crank!

lsberrios1 

Any race where they combine the Cat 3 field with the P12.

jhglaw

Riding home holding the stem in one hand due to breaking the elbow on the other arm

f4rrest

I'd get uber at that point.

79pmooney

For me that's easy; the 1977 Maine International. 105 miles, probably 5000' of climbing - many, many Maine hills. Fast race. I helped initiate a 6 man break midway that turned out to be a sprint for a pair of Hutchinson tires. Then 30 miles later, I was the last to make the big split, hung on and finished in the money, under the old course record and wasted to the core.

The hill 15 miles from the finish where I was #30 of single file was the single hardest thing I have ever done. Halfway I looked over my shoulder to see how many riders I could drop (hoping doing that wouldn't cause a permanent gap). The rider behind me was 25 yards back and fading fast. I knew at that moment the wheel I was on was beating that guy (and everyone else) by 10 minutes and I had a choice.

Ben

Da Reef

Today. 194 miles 11600' climbing. Training for Dirty Kanza in June.

patrickgm60

70-mile group ride that included Mix Canyon Road, in August. Group broke apart on MCR, only 3 of us reached the top, ran out of water, worst cramps ever. Wouldn't ride that route again if someone paid me.

dksix

Mine was July last year. If time riding MTB with a guy I had met when I saw him loading up from a ride near where I worked. We had mutual friends and soon after I started following him on Stava he invited me to come ride with him and a couple others. He had also followed me on Strava and was well aware he was well advanced of my fitness and abilities. He is there waiting when I pull in where we are to meet all but one other guy had failed to show that day.

Out of the parking lot we hit a pull that's about 3 miles and maybe 400' of elevation gain on a fire access road. I did OK, kept both the guys in sight until about the last 1/4 mile. From there the knext mile or so was little ups and downs going across the top of the mountain. Then it was time to desend, 45+ MPH down the switch backs, yes at that point the vastly different skill levels was well evident. By the second set they had checked out, I'd occasionally come to a clear section and see them on down the mountain.

That decent was about 5 miles long then we dropped out of the mountain on to a gravel road that runs along the river and is pretty flat. They kept a leasured pace on the flat that I easily kept up with. I was winded where they were able to converse between themselves without being out of breath. Then we got to the end of that road and turn on to a paved 3 lane rd that goes to the top of the mountain. The next 6 miles took me over an hour, on paved road. Then we went back off road which was pretty good for the first mile or so but the it turned into climbing and started raining.

The next hour or so was climbing in the rain. While I stayed to the main fire road going up the mountain the other 2 guys were cutting off on trails and doing single track that would periodically come back to the road so they could check on me. I was slow but still pedaling. About this time my phone got so wet it stopped working (I use it for my Strava). When I got to the top of the mountain they were waiting.

My phone had started drying out and was working but the touch screen wasn't responding. I put it in the mount and start down the mountain with confidence as I had written this section before on dirt bike (motor cycle) and way to that point when you get to tired to hold back. They took off and I took off trying to keep up. Maybe a mile later phone came out of the cradle and bounced about 30' down the road, broken display but the water must have leaked out the cracked glass because the touch screen was now responding. Came out of that section of mountain onto a paved road that I knew well and we took it easy headed back down to the river.

It was at this point it sank in that that 5 mile set of switchbacks down the mountain would be how we had to get back across that mountain. I know now that it's 1200' in 4.6 miles and after the rain had stopped the sun had come back out pushing the temp into the 90's at about 98% humidity. This is also the point I realized that i should have refilled my bottles when I had the chance. This was just going to be a 50 mile ride and I do that on road bike all the time and never have to refill.

I told the guys to go on I would be fine getting back and I didn't want to hold them. I did OK, considering, for about the first 2.5-3 miles. Not even having to stop and rest but that was all I had. From there I started riding and walking, then mostly just walking it and then I pushed for a solid mile to the top. They had done some more single track out the ridge of the mountain but were waiting me when I got to the top. The last 3 miles was a fun down hill, or would have been had I not been completely spent.

I made it back to the parking lot, where they both a cold water in coolers which I did accept their generosity at that point. We talked for awhile, I had pretty much recovered and they kindly invited my to go back in with them, they were going to hit some more single track that went off the other side of the mountain, Of course, I wasn't that crazy so I loaded up and headed home.

Apparently my phone stopped recording my ride when it go wet but restarted after the busted screen let all of the water out. I lost about a 5 mile section of mostly climbing, though not many miles. Trying to piece together what Strava recorded and information from the other's ride the day left me with about 46 miles and 5400' of climbing over the course of almost 6 hours. It was a brutal ride for me at that point. I've since rode all of it again, just not at the time. It breaks down to about 3 really fun rides.

silversx80

The first year I started road riding I was living in Albuquerque. I left my apartment and rode to Sandia Peak on a whim, in the middle of the summer. It was 35 miles to the top, and over 6,000 ft elevation gain just to get there, with the ride starting out at over a mile elevation. When I got home I collapsed and slept for 4 hours on the floor.

My longest ride prior to that was 30 miles, and I did 70 that day. That's also the day I fell in love with the road bike, and that route in particular. I used to ride it every weekend.

Worknomore

Keeping up with the A group for 30 miles then limping home 30 on a total bonk.

dirtydozen

It's all flat where I live and I was in holidays near the Col d'Aubisque.

I went to try a 6km climb that was supposed to be nothing compared to the Aubisque.

But damn man, first 2 km were ok, but then 4 km at like 11% average, I was just done. It was so hot as well. I was like : hey, first time you're riding in moutains ever, look at the landscape !

but all i could see was moutain moving and getting blurry just because i was so done

That was scary at some point, and made me nervous for the Aubisque 2 days after, i thought i would fail mesirably. But actually on the aubisque i had the best ride i ever had, started slow because i didn't know what to expect but then i was just flying

f4rrest

Some really cool ride stories in this thread.

Carbonfiberboy 

They vary - it's not obviously not just the stats, it's how your training and prep was the morning of. I think a tie between my first 300k, 9,000' brevet (13 hours ET) and a 400k with 15,000' (18.5 hours ET). I was in my early-mid 60s for those. It's true what they say about learning how to suffer. It's a skill. You think your pain meter is off the charts, but no, it really isn't. Another tough one was a 10,000' century when it was 104° at the base of the last 5,000' of climbing. That one wasn't the pain really, it was just figuring out how to continue.

kbarch

That's some heat - climbing in 80 degree weather is bad enough! I don't think I would have even started.
Some people don't ride in the winter because they don't like the cold. I'm planning shoulder surgery for July because if I'm going to have to take a break, I'm taking it when it's hottest out.

Machka 

This past weekend was the toughest riding I've done so far this year.

300 km on Friday ... supporting a 300 km on Saturday ... and then a 200 km on Sunday.

500 km in the space of 60 hours.

Steepndeep

I'd have to agree w/ Ultimate Challenge. Long w/ hard climbs, particularly Guardsman Pass. Did Lotoja 2015 also and it didn't seem so bad to me, except that I was feeling real nauseous from so many gels and drinks around 150 miles. Felt better the last 50 or so miles.

caloso

Everybody in NorCal talks about Mix. Kudos.

rico_mack

Without a doubt for me the Leadville 100 was my hardest ride. It's not a road bike race so i don't know if it counts.