Words: Jeremy Dunn | Photography: Chris Milliman | Date:

I’d been hearing about the fabled D2R2 for a couple of years before I actually had the chance to do the ride. The stuff of legend, stories were passed around like folklore at a couple of the local bike shops where I was working. “Dirt roads for over 100 miles” is what one person said. “You simply cannot do this ride on a road bike” was another sentiment. But it was really more about how they said it that was interesting. Even with the near-impossible nature of what they were describing, this was a ride these guys had done year after year. In fact, I have never met a person that has actually done this ride that wasn’t committed to returning the next year to tackle the roads once again.

All summer, our group had been talking about D2R2 as the carrot for which we hoped we would not also get the stick. Each of the other East Coast rides had offered something different to help us prepare for this established group-ride epic. The heat in Litchfield, intense climbing in the hills of Vermont, the steady rolling hills surrounding Fitchburg. Yet if someone had told us we were going to face all these conditions rolled into one ride, none of us would have believed them.

In the weeks leading up to the ride, I started to do some online research and some asking around. What did the survivors have to say about it? Most of what I found spoke of the demanding nature of the ride—the amount of food eaten, liquid drank, that sort of thing. The other commentary that kept coming up involved the guy who invented the ride, a rider named Sandy Whittlesey. Part Wizard of Oz, part army colonel with a touch of Grant Petersen thrown into the mix (the good part). Sandy’s persona quickly grew into legendary status.

Sandy lives up to the legend. And D2R2 lives up to the mystique. Mark my words, it will live up to anything and everything you’ve heard about. My only words of advice are to go into this ride lightly. Do not take it seriously because the moment you do, the moment that you do not stop to smell the roses, or stop respecting the hills that are continually pushing you back down, you will be defeated. If you can remember that, you’ll have a ball.

What follows is a series of e-mail correspondence with Sandy Whittlesey himself. Actually, it was just one e-mail but Sandy answered everything we asked so eloquently that we just let him go for it.

(As a side note, more than 100 miles into the ride fellow Continental rider PVB discovered that Sandy, who also went by the moniker “the Sandman”, was the welder that had fabricated a titanium seat post that Pierre still uses, 10 years later.)

Give us a little background on who you are? Education? Occupation?

I worked as a shop mechanic in high school and college. I have undergraduate degrees in mechanical engineering and computer science, and a PhD in biomechanics. I work as a self-employed technology consultant, mostly writing software and mechanical design. My favorite gig this year was collecting some data on the USA BMX team before they went to the Beijing Olympics; as they say, the greatest athletes humble you with both their skills and their modesty. Ultra Marathon Cycling Association (UMCA) members also know me as their chair for Race Across America (RAAM) qualifying.

How did you come to the discipline of cycling?

I’m known for my talent as a distance rider but I am better characterized as a very avid rider in every way: commuting, grocery shopping, traveling, visiting or just something to do with friends. Sometimes I’ll even bring lumber home on my bike. My parents got into cycling during the ’72 gas crunch, though as a kid I passionately hated riding because I was wretchedly thin and my little brother kicked my butt at it. However, growing up in Acadia (I see you guys did a ride there, too), the carriage roads, Cadillac Mountain, and Ocean Drive eventually won me over. I started racing at 15 and was a Cat II roadie for 20 years. I rode my bike to school and college every day. In the 1990s, I made a habit of taking 1500-mile weeks on a touring bike, with nothing but a tarp and sleeping bag – never a map. Midwest, Maritimes, wherever. I didn’t get my driver’s license until I was 34, by which point I had traveled in 38 states and 10 foreign countries on three continents. I’m notorious for appearing at business meetings wearing cycling shoes because pants and shirt are too much weight to carry. Last year I did fifteen 200-mile day trips to a consulting job in Providence, and I still ride 50 miles to the airport year-round.

At Rapha Continental we tend to lean toward “epic” with everything that we do. What makes this “little” ride of yours so epic?

The great thing about distance cycling, and randonneuring in particular, is that you are very much on your own against the course. In fact, it is generally counterproductive to get competitive with other riders because the course is your main enemy and will kill you (sometimes literally) if you don’t give it your full attention. So this was the format that I ultimately selected for D2R2: no mechanics, no follow vehicles, no prizes. Carry what you need and find your own way around.

One of the great things about epic rides is that they are so mental in nature. Ultimately your body deteriorates and there is no technology or chemical or anything other than your own mind that can find the way through it. Often, you see riders of very average physical ability doing very well in distance events because they have the perfect mindset for it.

How long did it take you to piece together the D2R2 ride?

The ride started in the early 1990s as a favorite dirt-road loop. In 1999, I put together a 70 miler to celebrate the 100th anniversary of Paris Roubaix. Everyone who did it felt I should make an event out of it. It still took me another five years to get the loop right. Western MA has the odd distinction of having many towns whose populations declined over the years because the Hilltown winters were so much harsher, the terrain was so steep, and the soil was so rocky. The slow exodus left countless old roads that nobody bothered to modernize. It’s at times creepy how many old foundations, cemeteries, stone walls and other reminders are out there in the woods, gathering moss. I use the term ‘capillary bed’ to describe the number of roads out there, and it’s probably the most unique element of the region. This is a key appeal of D2R2. Just like Acadia’s carriage paths, roads built for horse-carts, not cars, make the best cycling. Narrow lanes with tight turns and dips, wooden bridges, stone walls, big old trees, etc. And no cars. But even the best atlases fail to cover the vast array of roads out there, so the process of building a century loop was several years of look-and-see as weather and work permitted.

Over time, I dropped any analogies to Paris-Roubaix, realizing that I was creating a ride that embodied the coolest riding that my home region had to offer. I still counsel this to new event directors. In fact, just this week I was talking with a guy designing an ultra-distance race around Ireland: “Don’t try to be RAAM or the Tour de France or the Nissan Classic. Just make it the best bike ride you can imagine and people will come from all over the world to try it.”

Why is it epic?

Some days I wonder if D2R2 is really all that brutal or if it’s just that people – even from eastern Mass. – don’t believe that this state could have such a hard loop. They start the ride too fast and then blow up. If you blow up on D2R2, the course is a nightmare because the climbs are so steep. Actually, I think riders are finally figuring that out. Most are starting slower, with a 1-1 low gear and carrying a small backpack with extra food, drink, and bike parts.

In 2005, D2R2 was a weekly training ride in my preparation for Boston-Montreal-Boston, something to make Middlebury Gap feel familiar with 500 miles in my legs. You can call it epic just based on the numbers. At 112 miles with 16,500 feet of climbing, 70% on dirt, D2R2 is a bit longer than an Alpine stage of the Tour de France, with more climbing, a lot more steep pitches, and more than twice as much rough stuff as Paris-Roubaix. At least 16 hills exceed 13%. There’s 18% at mile 35 and 27% at mile 43, as well as 20% at mile 96. We shortened the course this year, had the best conditions (road and weather) ever, and finally a rider was able to break eight hours. Ten to 13 hours is a typical finishing time for most avid riders.

Do you ever go back and do it on your own? What are your favorite parts of this grueling route and are you always looking for new roads?

In July and August I ride some part of the course every week, checking out conditions and looking for any new construction but I rarely do the whole loop. There are so many roads out there and many that I have yet to try for the first time.

The irony is that I never designed D2R2 to be brutal and I don’t care to boast about the difficulties. I just wanted to include the covered bridges and my favorite vistas, the latter of which were on top of big hills. In between, I sought out the most primitive roads because they were the coolest. So yes, the result is damn difficult but I assure you, I could have made it a lot harder. In fact, the ride committee last winter suggested a couple of route changes that I vetoed because they added a couple thousand feet more climbing. I really want every rider to come here and say, “That ride totally kicked my ass but WOW, was it fun and beautiful out there.”

Putting a signature climb like Patten Hill at mile 100 is analogous to classic finishing climbs like the Poggio, Bosberg, and Cauberg but that is just good course design. The astute observer will note that the three miles leading into the Patten, by design, are paved, flat, and include a food store. Yes, the climb is murder but the view is awesome and where else are you going to ride such a cool road like that? They don’t make roads like this any more because they are ill-suited to cars or are prohibited by law, citing what a fire truck is capable of doing.

My favorite parts: Pine Hill Rd in Conway; the Vermont stretch (something about how the road bends, I just love it); and the Patten Hill district. The first edition finished on the corn-lined, 300 year-old farm tracks of Old Deerfield, though we have not been able to fit those into a loop since. Most riders say that Green River Road is their favorite and not just because it’s flat. It’s a pretty unique stretch there.

Tell us a little bit about the bicycle that you ride. Is it equipped in any special way to handle the rough terrain?

Many dirt roads here have a clay base treated with calcium chloride, so most are quite do-able on a road bike. When it’s rainy, I’ll use a cross bike with full fenders, more often with 28c touring tires rather than 32c knobbies. Otherwise, my favorite dirt-road bike is a rigid Columbus Max steel-tubed frame and fork with 25c tires, 185mm cranks, 46-34 rings and an 11-19, 7-speed cluster. All my bikes run old Suntour friction shifters and deraileurs. They are feather-light and last 80,000 miles. They always work, can interchange parts and cost $20 or less on eBay. Shimano shit is none of those things.

Do you have any favorite clothing requirements? Wool vs. Synthetic?

If it’s sunny and hot I usually wear a white, full-zip jersey. Dark colors make no sense for heat or visibility. If it’s rainy or cold, I always wear wool blends. And long-fingered gloves, even on a summer day, to dull the vibration and enhance grip.

Finally, I’ve heard rumors of other little epic journeys that you’ve done off-bike. Care to elaborate?

I guess you heard that I once hiked 62 miles home overnight for Christmas. It was on connected trails from Amherst, Massachusetts, to Hartford, Connecticut. There was three feet of snow on the ridgelines and the temperature fell to 8 degrees that night. It was memorable and actually a lot of fun despite the blisters.

Click cue sheet for PDF version.

Share this

Got something to say?