First Leg: Babylon to Blue Point--25 miles
I started out in a group who turned out to be too slow, so I followed a woman in a Luna jersey and a guy in a TNT jersey, and rode with them. They were a little faster than me, so I'd occasionally drop behind them and have to catch up. We didn't talk much at first, but eventually we introduced ourselves. I rode with them most of the way to the first stop, where I stopped and they didn't. The rest stop wasn't fully set up yet, so I couldn't refill my Gatorade. Refilled my bottles with water, went to the bathroom, ate a couple of fig newtons, and got back on the bike.

2nd Leg--Blue Point to Westhampton-25 miles

Jumped on to a very speedy group of three guys and a girl. We kept a loose, informal paceline, roaring past people on the road. Occasionally, someone would join the group, but they'd almost always drop off after a couple of miles. I think we averaged easily 20mh for this stretch. When we got to the rest stop, the girl needed to have her bike fixed, and the others waited for her, but I didn't feel like hanging around, so I had a pb&j, went to the bathroom again, and left, but not before running into the Luna girl from leg one, who was surprised that I'd caught up to them.

Leg 3- Westhampton to Water Mill-30 miles

This was the toughest leg. It was very flat, but right by the water and wide open with lots of crosswinds. Roads were flooded in places from the heavy rains the night before, and we had to squeeze through narrow swaths of dry pavement. I saw a couple of guys on tri bikes and chased them, just to give myself something to do, since I couldn't find any groups to jump onto. As we approached a big bridge, I said to an older guy who I happened to be passing, "Hey--our first hill!" and he said, "Wait till you get to Montauk. The screwin' you got is nothing compared to the screwin' your gonna get." Umm....ok...thanks, weird old roadie-dude. Once over the bridge, a group of 5 or 6 people passed me, and I was too surprised to catch them. I rode along for a while without seeing anyone in front of or behind me, so I thought I might be lost, and pulled over to check my turn sheet. A guy passed me on his bike and said, "Second guessing yourself?" And I said, "Yeah, a little,", but he said he thought we were on the right road, so I followed him. And yes, he was lost, too. After a few more wrong turns, we found the turn we'd missed in Southhampton and made it to the third rest stop.

Fourth Leg: Water Mill to Montauk--20 Miles

Again, I couldn't really find any more groups to ride with, so I just sort of hung with these three guys for a while. Eventually, I caught up to two other guys who were a little faster. I was starting to hurt a little, butt, hands, left knee, neck, and lower back. This is also where the hills started. First was a long stretch of Montauk Highway which wasn't steep but seemed to go on forever. Once I got over that, I had to get over a series of short, steep, sometimes curvy hills, one right after the other. Finally, I got into the town of Montauk, and looming about 1/4 mile away was a HUGE mo-fo'in hill. I was girding myself to attack it with what little I had left, when I happened to look down and saw a painted indicator on the road indicating a turn. Whew. I rode about another 2-3 miles to the finish line. My back hurt so much I could barely get off my bike, but I was done. 100 miles in the books, and by far my longest ride to date.

It might have been fun to ride the whole way with a group of people, but I sort of enjoyed it as a solitary endeavor.

Had a massage, which was a Godsend, since I was in a lot of pain. The masseuse was great, even if she did practically undress me in the middle of the lawn where everyone was hanging out. Had some food and about 5 gallons of water. Changed my clothes, rode to the train station and took the train home.


I wasn't trying to go as fast as I could. I don't know that I could have gone a lot faster than I did without really suffering at the end. Maybe I could have spent more time in aero, which I didn't do much of until the end, since I was mostly riding in groups.


Very well organized event. I'd do it again. It's kind of a bummer that you spend almost as much time on the train (1.5 hours to Babylon, and 3 hours or so home from Montauk), but it's a great ride, great scenery. The rest stops are well stocked and well run. Good mix of people from very experienced riders to newbies.
Oh--and the drivers were INCREDIBLY polite. In many cases, they would cross double yellow lines into the opposite lane to give us plenty of room when they passed us, even if we were in the bike lane or on the shoulder. I can't think of a single incident when a driver was anything but courteous. That was cool.