2011 D2R2

I would like to tell you not to come and ride D2R2 (The Deerfield Dirt Road Randonee). It is not the most organized cycling event you will attend. The route is sadistically hard. It is dangerous in many spots, and you do NOT have the right bike for it, no matter what bike you have.

And yet, despite all that, sometimes because of it, this is the single best cycling event I have ever ridden.

Unlike many rides which start with someone on a bullhorn giving nominal instructions at a start line, followed by a starters pistol or some other clear sign that the ride has begun, D2R2 invites you to leave when you’re ready. Ride up to the sign out sheet. Record your number and time of departure, and then get rolling. Go.

What you discover, once on the road, is that there is no signage on the course. No arrows. No logos. Nothing. You are entirely dependent, for whatever length (100K, 115K, 180K) course you choose, on the cue sheet.

Here are some representative samples from the cue sheet:

“Continue straight past “Road no longer maintained” sign”

“Continue straight past gun club onto very rough jeep track”

“Top of hill, farm animals often in road; CAUTION, hard right turn on descent”

“T-intersection, LEFT onto Cowpath 40!”

Stage 3: “A hard dirt climb, a very hard dirt climb, and then a super-hard dirt climb”

“CAUTION: Super-fast downhil with crazy turns and full stop at the bottom”

“CAUTION: gnarly descent, stones, washouts next mile”

Rather than turning the ride into an orienteering course for the velo set, though, this approach to navigation forces everyone to talk. You start by asking if anyone has seen the sign for Cowpath 40, and end up talking about where they come from, what they’re riding, what they ate, etc. It galvanizes the pack, which is a good thing, because there are spots along the way where you need as many friends as you can get.

Another issue is the difficulty of some of the terrain. There are not just steep climbs. There are steep climbs on dirt, and there are not just steep climbs on dirt. There are steep climbs on loose dirt, strewn with gravel and loose stone. And there are not just steep climbs on loose dirt, strewn with gravel and loose stone. There are steep climbs on loose dirt, strewn with gravel and loose stone that go on and on and on, until you’re sure you’re going to throw up and quite possibly fall over.

I was lucky. I had good legs all day.

Ride founder Sandy Whittlesey has done what so many of the iconic races/rides in our sport have done before. He has looked at the area he lives in, figured out where all the most interesting places to ride are, and connected them with a bit of ambitious cartography. This is not a ride that seeks to imitate other rides. This is a ride that tries only to show you exactly where you are.

The ostensible purpose of the event is actually to benefit the Franklin Land Trust, a group that “works with landowners and communities to protect their farms, forests, and other natural resources significant to the environmental quality, economy and rural character of our region.”

In this case, that means rolling farmland, rambling jeep tracks, absurd, escapist dirt roads that shoot up inclines and snake along ridges, paved bits that bisect primordial forest and everywhere the rumble of a river or a brook.

I have hiked, biked and traveled all over the parts of Western Massachusetts and Southern Vermont the D2R2 takes in, but I had never ridden an inch of Whittlesey’s route. He showed me what I’ve been missing.

We rolled back into the start/finish meadow around 5pm with the first drops at the leading edge of Hurricane Irene plopping heavily into the grass. The grills were sizzling, the smell of burger grease wafting on the wind. There was a line at the beer tent, and there were smiles on every face.

It would be easy to chalk up the joy of D2R2 to the scenery or to the hard-man difficulty, but that would fail to capture the spirit of the thing. Simply climbing really hard, technical terrain does not make a ride great. D2R2 takes you up those roads because that’s the only way to see what’s up there. And, of course, you get the descents. I touched 50mph on one of them, a sketchy paved track that swooped and banked like a drunken sparrow. It was, without exaggeration, the best descent of my life, the sort that mixes bowel-guttering fear with smile-plastering joy. At the bottom I could only manage a torrent of profanity to express the complex emotions I’d just felt.

In this, its seventh year, the D2R2 has grown into a big, happy, unruly mess of an event. The word is out. Just short of 1000 riders took part, and word of mouth alone will drive that number higher in 2012. I would like to tell you not to come.

But I can’t.

Photos courtesy of and © Andrew Conway.

Follow me on Twitter @thebicyclerobot.


  1. Peter Lin

    I love riding around western MA. It’s good to know there’s a lot more great roads/dirt roads/trails out there to explore.

  2. grolby

    I miss the roads in western Massachusetts like I can’t even tell you. I wish I’d been able to do D2R2 before grad school took me off to more southern climes. I’ll be back.

  3. Pascal

    Yes!! Now you know. I’m glad you had a similar feeling to what i felt the first time I rode those incredible roads, those descents that go through your head that night in bed while processing the day. It’s a real rollercoaster ride of emotions, sensations and effort.
    I was eating my ribs n burgers when you arrived. I saw you walk by but was a bit shy to say hi, plus I was kind of a rib eating, beer swilling zombie with not a lot of anything left in me.
    My teammate’s blog entry here:
    Looking forward to next year.

  4. Author

    @Pascal – I’m sorry we didn’t meet, although I can certainly understand your interest in food at that point.

    I should have mentioned some of the good folks I met during the day, including Peter from Barrington, RI. Some had heard of the site and were fans, others hadn’t, but might one day give us a read, so it was all to the good.

    I, too, am already looking forward to next year.

  5. MattS

    Hehe, I was sitting with Pascal as he pointed you out upon your return. My daughter said, “What, there’s a robot here?’ Hilarious.

    I think you’ve picked up on something I missed using a GPS this year: the hilarious and educational cue sheet notes. Next year I’ll be better prepared and have the notes on my screen so I can engage a bit more with the places we ride through. Its funny, I know exactly which descent this is: “CAUTION: Super-fast downhil with crazy turns and full stop at the bottom.” I was glad to have great brakes (cantis, seriously) at that full stop!

    Perhaps next year you’ll bring some RKP goodies to sell or raffle. I’d be all over a hat or bottle, and I doubt I’d be the only one.

  6. sophrosune

    I have been trying to find something that would explain to me the attraction and purpose of D2R2 and I have finally found it. They should use this piece in their brochure. I’ve wanted to ride this for some unknown reason, now I have a known one.

  7. Tim

    Great write-up!
    For years I’ve been riding the roads that D2R2 traverses with a great community of cyclists in the area(I actually live on the 100k loop). Sandy comes along sometimes, and last year we introduced him to Pennel Hill Road. I could see a big grin on his face when we got to the top, and I knew exactly what that meant. Welcome to our world, where we ride a 34 x 29 and 28c’s as standard equipment. Believe me, to ride any of the D2R2 loops, you have only scratched the surface of what is available out here. Sadly, many of the roads were descimated by tropical storm Irene. But fear not, this weekend several of us are going out to find roads around the roads that are washed out. Anyone care to join?

    Thank you for capturing the spirit of D2R2. We are the luckiest bike riders on the planet. Come back soon.

  8. Tremlett

    This is the ride I didn’t do before leaving New England, where I’m from. Thanks for a great blog, and no thanks to you, I will likely be in a sadistic amount of pain following next year’s D2R2.

  9. Marko

    Great narrative, and you so totally captured what I felt as well. I did this for the first time this year, too, and I’m hooked. My cycle computer said 49.5 mph on that downhill (with 32c cross knobbies), and I’m pretty sure I uttered a few expletives at the bottom, too. 🙂 I’ll be back in 2012.

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  11. aj gemperline

    I was there this year, it was my first D2R2, started out late because my car blew a tire. Did the 100k. Made a wrong turn at the lunch stop and ended up riding with people doing the 115k. To say the least the burgers and beers were even more tastier at the end. I will repeat and still use my C’Dale F3 hardtail mountain bike. Though I may go down to 1.5 vs 1.75. Going downhill hitting 43 mph on mt bike is both exciting, and scary at same time. There are no right bikes. On paved roads the road bikes rule, going up hill the mountain bikes tend to dominate to an extent as long as it is gravel. On the gnarly descent I was passing a lot of people, disc brakes are a great advantage.

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