I'm going to have to go with 53 miles for Day 1 of this year's Hilly Hundred in late October.(around Bloomington, IN). Weather conditions were just about the WORST for riding. Temps were in the low 50°F, windy, and it rained the entire day...from mist to downpours. But it was the best ride. Why? I got to ride with BOTH of my brothers. We're all in late 50s/early 60s. I've been riding for about 40 years, them only about 20. We all live in different states. It was the first time in all those years that the three of us got to ride together. Normally in the Hilly Hundred there are in the neighborhood of 3000 bikes on the road. But that day...during our 53 miles...we say just three other riders. Conditions were terrible. But it was awesome because I got to spend it with both of my brothers.
A close second was the ride I go to do along the Amalfi Coast in Italy while vacationing there in early October.
