I say "modern era" because 12 years ago I did do a 60 miler but that was before a multi-year layoff.
In my pursuit of a 100 miler I know I have to go on some longer rides. While fastpitch season is winding down I'm looking for opportunities to get in some miles. With this in mind I, at times, will go do a ride at night on the bike path. My kayaking buddy and I sometimes do night paddles as well. It's awesome.
So... on Saturday I call my buddy and tell him that if we get put out of the tourney early (we did) then I'm going to try and do a 30 miler, which was the next distance I wanted to accomplish. Super. One of use got the great idea to do it at night. I call my FIL and he is going to join in. Both my FIL and buddy have road bikes and ride way more than I do so I let them know I'll be the anchor. They don't care. We arrive at the parking place and get on the trail as it starts getting dark. A brief rain had just finished so we are going in the dark with a wet path and the sounds of a post-rain wet forest around us at times. It's great.
On the 15 miles "out" I go at my 100 mile practice pace of around 11 mph. On the way back I kick it up a gear (BAM!) and the closer we got I would keep evaluating and ether up my spin or up a gear (BAM!).
25 miles of the ride was fun. The last 5 was not but my rump was starting to feel the extra time in the saddle, my shoulders were sore, etc. All things I expect from stretching out a distance.
The last 1.5 miles I went as hard as I could. I would sprint until I couldn't stand it then coast until I could go more. At the finish line I was toasted.
We finished at midnight. My buddy came back to my house to drop off my bike and we sat in my driveway enjoying a post-ride beer. That was a great beer.
The night ride was so awesome that we think we will do more. And once I do my 100 miler we plan on doing another at night.
While on this ride I remarked "I sure hope no deer cross the path and take us out...". Then about 15 minutes later we hear what must have been a deer about 3 ft (seemed like it) away spook, run with the path (while in the woods) for about 10 feet then run off. During that 10 feet I was waiting for it to cross the path and skewer one of us.