About D2R2

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.  However, D2R2 will continue to maintain is original character as just a bike ride –

  • 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.
  • 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.
  • The event is a key fundraiser for the Land Trust's efforts to preserve land in the region, but the route sheets will always be available on its website for free.

What is D2R2??? 
Sandy Whittlesey
, ride designer says:


 “D2R2 is one of the hardest century rides in the world….  We designed it by placing pins in the map where the covered bridges and coolest sights were, then connected the dots with dirt roads.  The flat valley roads of this region are mostly paved; the dirt roads access the remoter areas, and it is steep terrain.  Our intent was to make the most beautiful ride we could …all we really want is for people to finish D2R2 saying, ‘Wow, that was really challenging, but totally worth it because it’s such a great bike ride.’…Please come planning to spend a full day out there, forgetting about your cylcometer, stay within your comfort zone and have a really great time on some of the most beautiful roads you’ll ever ride.”


 Everything about this ride is extraordinary; over 12 years of planning by Sandy went into this event.  Riders will enjoy a fabulous network of secret back roads and horse-cart lanes through some of the most scenic and historic areas of western Massachusetts and southern Vermont.  The constantly twisting route is often only one lane wide.  Rest stops with refreshments will be staffed by area volunteers and we are continually upgrading the quality of the refreshments based upon rider’s suggestions.


Stone walls line the roads far more than double-yellow lines.  There are dozens of maple-tree “allies” over 20 miles of rushing streams, four covered bridges and countless farms, fields, and forests.  Riders may expect hours of cycling without a single car passing.  The lunch-break checkpoint is a little park with a National-Historic covered bridge, timber-crib dam, and a swimming hole that has been called one of the most scenic spots in New England.


Bicycles should be equipped with triple gearing and slightly wider tires (i.e. 25c-32c).  Road conditions range from smooth clay to stony washout and puddles. 


Seven key climbs reach 1400-2000’ elevation, and 16 smaller pitches exceed 13% gradient, including a 25% wall.  At mile 90 riders will tackle the hidden back side of the lovely Patten Hill District starting at 20% grade, the road narrows to a bumpy 8’ land and ascends 960 feet vertical in 1.5 miles to a grand overlook toward Vermont.




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Franklin Land Trust, Inc.  679A Mohawk Trail, P.O. Box 450, Shelburne Falls, MA 01370