It’s only by coincidence that D2R2 is a cute reordering of the name of the beloved robot in Star Wars. It actually stands for something: Deerfield Dirt Road Randonnee. It’s a rugged gravel road bike ride in western Massachusetts starting down the road from historic Old Deerfield. Most of the ride is on dirt roads that vary in quality from fast hard pack to loose gravel with a couple outright trails thrown in. Oh, did I mention it’s 180 kilometers long and the course is not marked? Yup, that’s what makes it a randonnee. You are responsible for your own route finding using a cue sheet provided by the organizers or a GPS download of the track. Finally, according to who you listen to there is anywhere from 12,000 to 15,000 feet of climbing, including one wall with a 27% grade. It is easily the longest and hardest bike ride I’ve ever attempted.

Preparation consisted of as many long bike rides as possible. This included a rugged 100 kilometer mountain bike race in Carrabassett Valley, Maine, a 55 mile dirt road hike-a-bike epic through the backcountry near Sugarloaf Mountain, a 100 kilometer gravel road ride on Prince Edward Island, Canada and a 51 mile mountain bike ride on the trails around Portland. The key to all these rides was they lasted 4 to 8 hours. I also did many, many shorter rides on the road and mountain bike. Even with this training, I was extremely nervous about the D2R2. The amount of climbing alone had me in awe. I’d never done a ride with even half that much uphill.

We camped in a fallow farm field not far from the Deerfield River. The organizers did a great job the entire weekend, serving meals and having plenty of food on the road. At 6:00 a.m. Saturday August 22, my group of four set out. 180 kilometers is roughly 112 miles, so naturally we decided to add an extra 5 right off the bat by taking a wrong turn only 2 miles in. We got squared away relatively quickly and I tried not to dwell on those extra miles.

Slogging up a climb with Bill Yeo, 6’6″ and all-around great guy.

I was quickly astounded at the number of climbs. Around Portland if a climb lasts more than a minute or two it’s considered long. At D2R2, there were many that lasted 10 to 20 minutes, most of which was spent in my easiest gear, a 34 x 34 (don’t even think about doing this ride with a standard drivetrain!). They were steep and unrelenting. Blowing my mind even more were the descents. Some were terrifying with loose gravel that made keeping in control difficult. The cantilever brakes on my cyclocross bike were simply not a good match for these high-speed descents. My hands were sore for days after squeezing the brake levers so hard. Next year I will have disc brakes without a doubt.

D2R2 profile – an upside down saw blade

Despite the length and the grueling climbs, what overwhelmed me the most was the incredible beauty of the course. I was familiar with the area after spending four years in college at nearby UMass-Amherst, but I had never been on these back roads. The course wound its way through Deerfield, Ashfield, Hawley and then up into Vermont before looping back down to Deerfield. We were surrounded by lush forests and green farm fields. Many of these places bore signs indicating they were saved from development by the Franklin Land Trust, the organizer of the event. It was good to see my entry fee was going to such an outstanding cause. Check them out here: Franklin Land Trust.

We kept the pace moderate to save energy along with eating and drinking as much as possible. I felt good the whole day, almost as if under the influence of some drug. It was easily the most enjoyable ride I had ever done. It was with a feeling of great accomplishment that we approached the finish line a little more than 12 hours after setting out. There were delicious burritos and cold beer waiting our arrival.

The happy gang at the finish

Here’s an awesome video of this year’s D2R2 from Gravel Cyclist. It really gives you the sense of how great this ride is:

This is a must-do ride for the serious cyclist. There are shorter options including 160 km, 115 km, 100 km, 40-mile Green River Tour and a 20-mile Family Ride. And it’s also a way to support a great organization like the Franklin Land Trust.