Pretty sure one of if not my most miserable day in the saddle wasn't when I was young and stupid but actually when I was old enough to know better. The day coming home from one of the early Maggie Valleys. Not sure which year. Was leaving at about oh dark thirty as the plan was to do the roughly 800 miles all in one day. Don't remember what but apparently had something that needed to be done the next day.
Walk out that morning and two or three others are stumbling out at the same time. Leo from Chicago and a couple others I can't remember. A hard skim of ice is on every bike and car surface. Had an old Garmin GPS that I'd left in the tour pak overnight that was hard drive based. It wouldn't start up; it just said screw you, call me later. It was like 22 degrees. There had been a really heavy fog and it was still hanging in low areas. it was miserable.
Got geared up with the electric jacket liner and gloves, two pair of the warmest warm socks I had and the ultra uber duty long johns I'd brought "just in case", fired up the bike, the seat heater and the grip heaters and off we went. In and out of the fog on the short stretch to I40 and it was enough to get the jeans moist so stopped and added the rain gear as a top layer. With that it actually wasn't bad (but it had gotten a little cooler too!).
Got lined out on the highway and by the time the sun came up it was all the way up to 28 degrees. Didn't see temps above freezing until Nashville. About an hour west of Nashville the rain started in what was maybe 45 degree temps. Rains anywhere from moderate to too damn hard lasted all the way home. Another 350 miles or so. Don't think temps ever got above 55 or so all day and it was 8:30 that night with the last two and a half hours or so in the dark cold rain when I pulled in to the house at the end of what was probably a 15 or 16 hour ride. The day may not have reached maximum sucking potential (it was a bike ride after all); it rated way up there though

.