Back in early September I participated in the Rapha Prestige New England with about 25 other teams of four in the southwest corner of Vermont near the town of Rupert and the Green Mountain National Forest. Having never done a Rapha Prestige, I asked myself a lot of questions before the ride. Do I really need that extra tire and 4 tubes? Will that chain breaker and missing link come in handy? I’ve done long rides before and never had the misfortunate of a blown out tire or broken chain, but would this ride prove different? On top of that, who else of my friends are crazy enough to want to attempt this with me?

Bryan Banducci, Ben Newell and Jordan Eipper all agreed to join in the end and by 7:30 PM Friday night we off, headed north via the Taconic State Parkway. We still weren’t certain where we would stay the night, but about 5 hours later there we were at the start point. We scratched plans to crash the parking lot with tents and instead found a secluded area next to a nearby rail trail. We backed the car in, pitched our tents and all got the worst 4.5 hrs of sleep we could get.

After brewing coffee, we packed up our things and retraced our steps back to the start point from the night before. I had to be there for a 6:30AM captains meeting where we got cue sheets, turned in waivers and the organizers reiterated that we were participating in an “unsanctioned group ride.” There were many familiar faces, most better rested than our own. Time ticked away and we prepared our bikes, savoring the lingering smell of goat cheese from the farm we parked on.

Eventually our start time came. Even though Jordan was still at the car messing with his gear, we had a group photo taken and we were off. From the get go there were questions about navigation. Did we make the correct turn out of the parking lot? Ben, Jordan and I all had the route in our Garmins, Bryan fessed up to not knowing how to use the navigation feature. We passed a few teams after a bone-rattling, washboard descent that probably punctured a few tubes.

We descended into Danby after a few initial bumps and then were presented with our first significant climb of the day up Mount Tabor. Our group split up pretty quickly but we managed to regroup after crossing the Appalachian Trail. The point of the Prestige is to finish as a team, after all. The small town of Peru offered a chance to refuel which we took without hesitation. Many other teams did and it was at that café that we realized former USA CX Champion and all around awesome guy Tim Johnson was on the ride.

From there we began a seemingly never-ending climb up and around Stratton Mountain. Like every other mountain and ski area in the Northeast, there were tons of snowboarding and skiing stickers on every street sign. Unlike other ski areas, this one stretched for almost 20 miles. For the first couple miles the street signs made me smile but after five miles I started to thing I was in some sort of weird Escher-esque drawing. We passed multiple teams with members pushing each other up and generally looking pretty shelled.

If you’re climbing for a while, that means that eventually you get to descend for a while, too. Kelly Stand Road crested and from there it was all downhill for ten miles through a beautiful river valley. Hurricane Irene had decimated the road four years prior and it was just rebuilt last year. The perfect grade and extremely wide roadbed certainly made for a surreal descent. A couple teams got flats on the descent including ours. I waited up for Bryan to swap his tube while he told me about Ben Wolfe, another local crusher who has represented the US in U23 races in Europe. Ben was doing the Prestige for fun alone.

A quick stop at a Stewart’s to refuel and we were off, cruising along a river, passing people floating in inner tubes and under the only covered bridge of the route. We again started climbing, this time through extremely punchy and dirt climbs. Our group started to get spread out across the road but we regrouped for the descent. After blowing past our last food stop, we realized the mistake we had made and asked a few locals for some hose water. The climb following was certainly the steepest of the day. It just kept getting steeper and steeper until it crested. On the following descent we turned down a cooler full of beers with Tim Johnson, knowing there was still climbing to be done.

The last climb of the day wasn’t necessarily the hardest, but with 110 miles in your legs, most climbing is hard. I had forgotten that punchy climbs sometimes warrant punchy descents and on the following descent, our team got four flats. I doubled flatted, Ben slashed his rear tire and Bryan flatted his front. After wondering why I’d brought all those extra tubes and equipment for 112 miles, I finally had an answer. We all moped and changed our tubes, Jordan helping me with mine since he was the only to have not flatted. Many teams whizzed by us including Tim Johnson and his team who yelled, “Catch you at the finish line.”

Having just finished pumping our tires back up, we all hopped back on the bike and started to chase Tim and his group. We only had about three or four more miles and for whatever reason, we all decided we wanted to try and beat Tim’s group. Bryan and I hammered up to their group, Jordan and Ben yo-yoing off my wheel. I figured we for sure wouldn’t stay together. Bryan and I pulled through a few times and I looked back to see Ben sitting there smiling, Jordan just behind. We crossed the line just before Tim and even though they started 20 minutes after us, we had beat them in our heads. We certainly did catch Tim at the finish line.