D2R2 - The Deerfield Dirt Road Randonnée
August 19, 2017

The Deerfield Dirt-Road Randonnee was conceived in the 1990's as just a favorite dirt-road loop in the hilltowns of Franklin County, Massachusetts. Since its birth as an organized event in 2005, many have hailed D2R2 as the hardest, most beautiful, most fun, most traffic-free, most unique, and overall best ride that they have ever done. 

  • The courses will use the narrowest, oldest, twistiest, quietest, and most-scenic roads available.
  • A range of courses will provide access to novices as well as challenge the world's strongest riders.
  • D2R2 will never offer prizes for anything other than gags, nor will finish results ever be presented like it was a race.
  • The course is not marked.  Riders will use cue sheets to navigate the rout. 
  • Riders shall cover the course in a self-sufficient manner, without motorized crew vehicles.
  • The organization will put as much effort into its food offerings as it does the ride itself.
  • D2R2 will remain a key fundraiser for the Franklin Land Trust's efforts to conserve land in the region.


“At the Deerfield Dirt Road Randonnée, or D2R2, you start whenever you want and navigate your own route, you won't get a prize for finishing first, or grief for finishing last—and, by the way, you will fall under the spell of the most beautiful hard roads you've ever ridden.”

MIKE MAGNUSON for Bicycling Magazine


What is D2R2?

Each August over 1,400 bicyclists descended on Franklin County to participate in the nation’s largest dirt-road cycling event, the Deerfield Dirt Road Randonnée. Hosted by Franklin Land Trust (FLT), last year the ride attracted cyclists from 26 states and 5 countries.

This year, which marks the 13th anniversary of the event, promises to be the best attended yet!

“D2R2,” as the ride has been nicknamed, offers six dirt-road courses ranging in length from 20 mile Family Ride to 116 mile challenging course. All routes begin at Old Deerfield and thread through agricultural land and forests in western Massachusetts and southern Vermont. The short course has a flat run up the Green River valley, whereas the long course is regarded as perhaps the hardest century ride in the world. 

Randonneuring is a vintage French format in which riders are challenged with hard courses but encouraged to keep the atmosphere social. There are no prizes, and riders start in small groups at their leisure; however, the ride is timed and many participants aim to better their time from last year. The randonneuring style also engenders a level of self-reliance – riders must navigate the course and perform their own repairs. 

One of the things that makes this event so unique, according to Sandy Whittlesey, Ride Designer is that it attracts cyclists from a wide range of disciplines, from competitive road racers to recreational riders and mountain bikers. “D2R2 has a very egalitarian culture. Nobody cares how fast you are, what your background is, or what you’re riding.” Whittlesey has resisted suggestions of turning D2R2 into a race, or marking the route to make it easier to navigate. “We started the event with a stubborn insistence on the non-competitive, self-reliant style – if you wanted a race or a guided tour, there were lots of those out there. As a result, we ended up with an incredibly cool, friendly, strong group of participants, and we feel very lucky to host such a fun crowd every year.”

In twelve years, D2R2 has grown into the largest fund-raising event for the Franklin Land Trust, with entry fees being boosted by merchandise sales, raffles, and corporate sponsorships. The Franklin Land Trust (FLT) is a non-profit organization in Shelburne Falls, Massachusetts that conserves farms, forests, wildlands, and other natural resources in western Mass. In many cases, conservation restrictions aimed at encouraging agriculture and forestry are the conservation tool of choice, where FLT holds the restriction, and the land remains in private ownership Because FLT isn’t being asked to purchase the land, the result is far more land being conserved per dollar: last year, each rider at D2R2 effectively helped to conserve an entire acre of land – something that surely makes all the steep hills and bumpy roads seem well worth it. 

This year’s event will take place on August 19, 2017. 


Course Options

D2R2 includes courses to suit any rider. 180K, 160K, 115K, 100K, 40-mile Green River Tour & 16 mile Family Ride.
This year we have even added a Mystery Ride!

Learn More

Bring the entire family!

Each year, more and more riders are bringing their families along for the ride.  Some participate in the Family Ride while others enjoy the bounty of area attractions including Historic Deerfield, PVMA's Memorial Hall Museum and Indian House, Shelburne Falls, Yankee Candle, Art Galleries and so much more.

Camping | Lodging | Area Attractions