In Print: New England’s Deerfield Dirt Road Randonnee


Words: Jonathan Wolan Illustration: Stephen Haynes

Is thunder and lightning at 5am an omen on the day of a big ride? What if that ride travels up some of the steepest dirt roads in the Green Mountains? On the morning of the infamous Deerfield Dirt Road Randonnee those were the conditions I was facing. It rained treacherously for the entire two hours it took me to drive out to Deerfield, Massachusetts. My bike got soaked, as did the course, yet miraculously everything seemed to work out for the best. By the time my buddy Brad and I lined up for the 9am start, the clouds had cleared and sunshine poured down through the trees  throwing warmth on the hills and valleys along some of the most scenic roads in New England.

For several years, I’ve enrolled in the epic experience more commonly known as D2R2. This long meandering journey starts off in Deerfield, Massachusetts, wends into the foothills of Southern Vermont, and then loops back into Deerfield along the Green River. The route runs primarily on dirt roads (hence the name) and up some of the steepest climbs I’ve ever ridden or seen. One particular climb even boasts a 27-percent grade. This climb is so epic, a live band cheered us on. You don’t see that on every ride. There are several route options to accommodate a variety of riders. Over the years I’ve been most successful with the 100k route yet I once attempted the 180k route. The results of that ride were humbling, to say the least.

One particular climb even boasts a 27-percent grade. This climb is so epic, a live band cheered us on. You don’t see that on every ride.

As for the format, D2R2 is a mixture of biking and navigating. A randonnee is typically an unsupported long distance ride that follows a specifically predetermined route. Riders are given cue sheets (and sometimes maps) and then are allotted a certain amount of time to complete the route. Some randonnees are so long, they allow riders to sleep between legs of the route. These official randonnees are sanctioned by a governing body (Randonneurs USA in the United States). One of the oldest rides in the world, the Paris-Brest-Paris, is a very storied and famous 1,200 kilometer event held every four years. One key feature of riding a randonnee is camaraderie. Randonnees are not races so riders often work together on navigation. They also foster an atmosphere of cooperation. At various checkpoints, riders need to get a brevet card checked as evidence of completion. These locations are often referred to as controls.

The good people at the Franklin Land Trust created the D2R2 almost a decade ago to help sustain the pristine beauty of this small but integral ecosystem. The many farms and fields that riders pass through directly benefit from the money raised through the D2R2. In fact, after the 2011 D2R2, Hurricane Irene devastated the region so badly that many of the famous landmarks along the route were destroyed. The organizers took up a second collection after the ride and helped restore some of the beloved parks and covered bridges that are the quintessence of rural Vermont. So what’s over 8,000 feet of climbing in 65 miles if it’s for a good cause? Nothing at all.

After our initial panic of the rainstorms, the day started auspiciously enough when Brad and I tackled the first hill at mile seven. A seemingly misinformed randonneur, complete with fenders and Carradice bags, struggled to maintain his balance up the almost vertical loose rock of the first major climb. Unfortunately, his white-walled slicks were probably not the best tire choice for the dirt roads of Vermont. Even on my mountain bike with treads, this hill was a struggle. As he inadvertently swerved across our lines, we both lost balance and fell over. This was not a great way to start the ride.

What amazed me the most about meeting other riders was the variety of bike choice. I usually choose to tackle the dirt roads with a hardtail mountain bike, yet some people ride the entire route on road bikes with 23c tires.

After the first climb series and up to the first water stop, I struggled to find my rhythm. I remembered from previous years that these are not the kind of hills you can thrash. I needed to just pick a low gear and go slowly. There’s also no shame in dropping to a 1:1 ratio when there’s no prize at the finish line. In fact, randonnees require as much orienteering as athleticism. The finish line is the prize. So as Brad and I checked and rechecked our cue sheets, we both just let the ride happen.

While most organized races foster some camaraderie, but mostly competition, D2R2 focuses only on the former. With no GPS signal and limited cell phone service, groups of cyclists band together for practical purposes. Frequent flyers, such as myself, lead newcomers through the vaguely familiar landscape of farms, dirt, and hills. Thus we met with a couple fellow cyclists in need of assistance along the way. The addition to our group only enhanced the experience. What amazed me the most about meeting other riders was the variety of bike choice. I usually choose to tackle the dirt roads with a hardtail mountain bike, yet some people ride the entire route on road bikes with 23c tires. The more popular choice, naturally, are cyclocross bikes. Yet, I even spotted a few fat tire and full suspension rigs along the course.

Editor’s note: This feature originally appeared in Bicycle Times Issue #32. Order one here, or best of all, order a subscription and never miss an issue.

When our faith seemed pushed to the limits at Mile 35, the iconic red covered bridges appeared before our hungry eyes. The lunch at D2R2 was superbly catered by local businesses and has yet to displease me. I was happy to see that the romantic covered bridge and park were restored to their former glory following the devastating floods of Irene. Pictures from last year’s ride were fresh in my mind as merely hours after finishing in 2011, several inches of rain obliterated the glorious New England emblem. However, through the fundraising efforts of the Franklin Land Trust, nearly all the roads and landmarks were salvaged and repaired.

After lunch, the course ran flat alongside the Green River giving us a chance to spin our legs before the last tough climbs. This relatively flat dirt road lets even novices enjoy the splendor of the landscape. After about ten miles, the course darts upwards towards the last hill section.  As our legs begin to feel like wood, Apex Orchards appears at the top of our last climb. This final push up a stepped incline is rewarded with fresh peaches and plums from the local orchard.

Back at base, which at this point might as well be heaven, we’re treated to pints of Berkshire Brewing’s Preservation Ale and enough barbecue to beat the band. After a long hot day in the saddle, it tastes amazing. As the bonds formed out on the roads, between wrong turns and lost cues, continued over food and drinks, I felt relief and pride that our efforts helped to preserve the very landscape we traveled. Through forests, over rivers, and up mountains, we rode to preserve the source of all good cycling: beautiful land.


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