Ride for the Land
The original gravel grinder returns August 22, 2026.
Registration is now OPEN.
Video by Doug Mason. Riders: Eric Protulis, Patrick Parker, Tom Winter
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.
We’re marking 21 incredible years since this iconic ride first rolled through the scenic hilltowns. What began as a single route dreamed up by the legendary Sandy Whittlesey has grown into the beloved event we all know and cherish today.
It's a community, not a competition.
The route up the hill was dirt in some stretches and asphalt in others. We slogged upward through one ageless, panoramic view after another, until eventually we took a left onto an asphalt road lined with open fields, and this road climbed to the top. We could see it.
The whole way was lined with riders slowly straining upward. Maybe 100 riders were strung across this next mile, maybe 200, with not a cloud in the sky and not a puff of wind to push us back and nothing but green fields stretching in all directions.
In all the years I had been riding bicycles, I had never seen such a sight as breathtakingly beautiful.
Mike Magnussen, Bicycling Magazine, 2014
We ride for the land
Over the years D2R2 has evolved into a cherished tradition, offering not only an exhilarating ride but also a unique connection with the natural splendor of our region.
As cyclists, you've encountered firsthand the lush landscapes, meandering dirt paths, and tranquil wilderness that make this ride exceptional.
Landscapes like these are more than just views, more than just adjectives like “scenic” and “breathtaking.” They support ecosystems, and agrarian ways of life, that are quickly disappearing due to climate change, the relentless pressure to develop open spaces, and escalating demands on our natural resources.
To persevere, we need your support more than ever.
Crossing the Massachusetts boundary at the village of State Line, I find the roads excellent; and, thinking that the highways of the "Old Bay State" will be good enough anywhere, I grow careless about the minute directions given me by Albany wheelmen, and, ere long, am laboriously toiling over the heavy roads and steep grades of the Berkshire Hills, endeavoring to get what consolation I can, in return for unrideable roads, out of the charming scenery, and the many interesting features of the Berkshire-Hill country.
Thomas Stevens, "Around the World on a Bicycle," 1887
Route Choices
80K Point to Point Ride (NEW for 2026!)
Take a trip to Florida and experience a steady descent back to Greenfield, with the steepest climbs at the start of the route. Entry fee includes transportation to start location.
180k
The original, the legend, the ride that started it all.
160k
Back by popular demand, the original 160K (with some new sections for 2026!).
105k
With over 7000 ft of elevation, this route steps it up a notch from the traditional 100k.
100k
Only here is this thought of as "the short course!"
THREE route options for 2023.
92k
A route for those looking for more distance and challenge than the Green River Ride, but not quite as much as the classic 100k.
Family Ride
The hills are minimal, totally doable pulling a trailer.
Green River Tour
Enjoy the mystique of D2R2 without having to climb mountains!