Sixteen of us headed out at 4am from Westfield, our bright lights shining down darkened, desolate farm roads. The red moon peeked out from behind some hilltops; the idea was to see it again about 24 hours from now. Matt, Brad, and I wanted to ride straight through, only stopping at the seven checkpoints along the way. As I gave my bag of ‘stuff’ to Matt’s wife Mo, who was going to meet us along the way at the stops, I was quite aware that anything could happen after being on a bicycle for so long. My stuff includes arm warmers, cold coffee drinks, Coke, Gu, and Cytomax.

We rode the first leg with a group of about seven, including Matt, Brad, Chris, Jan, Ernie, and a few others. One rider was telling me about his upcoming Vespa scooter vacation in Provence in August, it was going to be a Ducati vacation but something happened with the Italians. We saw some deer, giving us fair warning we were headed up into the mountains where an assortment of crepuscular critters such as moose, bear, and marmots abounded.

We skirted the top of Connecticut, on relatively good roads. At one point we bear right at a fork in the road, appropriately marked with a giant 30 foot tall statue. At one point we are bombarded in all directions by microscopic glass beads from a fresh white paint line. We are down to Matt, Brad, Jan, Chris, and me after the first checkpoint at 100K over the NY border. We go over the Hudson, with a great view of the river below. Next stop was the bike shop in Woodstock. We stoke up on Cokes, delicious watermelon, and homemade brownies. Jan says he was going to rest up, so four of us started out to the next checkpoint at Windham. Before we got there however, there was some major climbing. When we get there, Chris bows out to rest a bit. Matt, Brad, and I started out for Schenectady. We are briefly peppered by some light rain giving me a slight chill on some descents. Once we came down from the high farmlands, the air warmed up considerably. We moseyed through the town of Saratoga Springs, then out again into more farmland. As we watched dusk settle in, groups of deer sentinels perched far off in the fields, monitored our progress along the roads to the town of Cambridge, host of the spring race classic ‘Battenkill Roubaix’.

We had a leisurely stop here about 30 minutes. Brad considered stopping for a while to rest, decided to continue on with us after a quick shower, change of clothes, and a bite to eat. We were back on the bike, on our way to Bennington. Right outside of town, a mother of all ascents awaited. We started to climb. Water in a rocky stream ferociously crashed to our right, rambunctiously tumbling down the mountain, shouting, this way, this way, not that way, you dummies. It got steeper. Cars went by us, lighting up the towering road ahead, there was no respite in sight, just towering dark outlines of endless trees. We finally reached the top after over an hour of climbing. We then we saw a very welcome set of road signs. First, a ‘runaway truck’ sign, replete with yellow blinking lights, then a ‘truck on a piece of cheese’ sign. Sure signs that a monstrous descent was up the road.

The full moon was out, floating in between marbled clouds high above us in the sky. I remembered this section from a Boston 600K from years ago. It had a nasty climb and some windmills. Good news is I was coming the other way, so we had a zinger of a descent coming up. The dark outline of windmills silhouetted against the dark sky appears to our left. The descent begins, but not before Brad yells “MOOSE” and off to our left in the woods, is a huge brown furry outline of a moose, with crashing of breaking sticks, bushes bending, whooshing, and Brad’s light shining on the beast. Holy moose. We then started descending, quickly. If any animals were going to get in our way, our awesome lights would give us a good view of them before we smashed into them.

We then started a desolate, interminable stretch of road along a river, but we scooted along at a good clip. We got into Shelburne Falls, where Brad said he had to rest on a park bench outside the control, till sunrise. We were all pretty shot, but making a decision to stop this far in is respected. Matt and I then proceeded to do the last 50 miles at a brisk pace. We wheeled into the start a little before 4am to meet our less than 24 hour time goal. We later learned Brad had gotten home around sunrise after a short nap, but not before seeing a bear.

This was a great ride, with great company, and great support.