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D2R2 Ride Info

Included in your Registration

  • Continental Breakfast (for 180K, Mystery Ride, 160K, 115K, 100K, 50M Paved, and Green River rides. Additional charge for the Family Ride)
    • Served from 5-9 am. Eggs, sausage, oatmeal, yogurt, muffins, pastries, bagels, coffee, tea and juice.
  • Checkpoint foods to include: fruits, PB&J, cookies, Real Pickles, Gatorade and water
  • Lunch
    • Along the Green River for 180K, 115K, 100K, Green River Ride and Family Ride.
      Served from 10:30-4 and including sandwiches, salads, chips, soda and water. (please contact us if you have food allergies)
    • Up in the hills for the Mystery Ride and the 160k. Served from 10-2 and including sandwiches, salads, chips, soda and water. (please contact us if you have food allergies)
  • Dinner served from 2–8:30 pm. (for 180K, Mystery Ride, 160K, 115K, 100K, 50M Paved, and Green River rides. Additional charge for the Family Ride)
  • A free pint of our Preservation Ale by Berkshire Brewing Company (served from 2-9 pm)
  • Commemorative D2R2 Pint Glass
  • Bragging Rights. Smiling volunteers. Beautiful scenery.
  • And the satisfaction that you have contributed to the preservation of Open Space and Farmland in western Massachusetts.

The Ride

Every route is beautifully scenic.

The 12-Mile and 40-Mile rides are fairly flat. All other routes include significant climbing and descending, with its physical and technical challenge.

As the length of routes increase, the variety of “roads” widen to include forest roads, jeep tracks, and trails. By the time you get to the Mystery Routes - all bets are off.
We assume increasing technical skill, not just fitness, as the routes grow longer.

If you haven’t ridden similar terrain we recommend starting with our shorter routes and coming back for more in subsequent years.

There are bailout options from each checkpoint, but they may still be challenging routes home.

Course descriptions

Rules of the “road”

The ride follows such little-used roads that you won’t see cars for long stretches. When you do unexpectedly encounter traffic the drivers won’t expect to see you, and may not.
So ride on the side of the road, only one or two abreast, and be cautious of the limited sight lines.

Don’t form large packs. This is not a race, and you’ll do better if relaxed. Please be respectful of everyone else using the road, especially as many others will be surprised to see anyone else on their road. Help cars pass and turn. Pass tractors carefully. Say hello when approaching horses so they know what and where you are. FOLLOW THE RULES OF THE ROAD!

Rest Stops

There will be checkpoint rest stops supplying water and food at least every 30 miles (usually every 20). You get one spot with full lunch and elsewhere a selection of snacks.

Rest stops have an opening and a closing time, so you must arrive between those if you want food. If you’re not going to make it in time bailout directions are available at each stop.

There are a few stores on some routes, so carry money to supplement the rest stops.


The routes of the D2R2 are as a true randonnee, where navigation is part of the challenge. You are responsible for your navigation tools and skills. We provide turn-by-turn directions and sometimes even a sign or two, but many riders still miss turns so please pay attention as a randonneur should.

The cue sheet is the primary navigation aid and has the most complete information about hazards and ambiguous turns.

GPS files will be provided the week of the ride.

Current maps, cue sheets and GPS files are available for 2019 except for the Mystery Ride.

Maps and GPS files have inconsistencies so the cue sheet is best. If you intend to use a GPS to navigate the route, please read through the cue sheet pre-ride as it also contains important cautionary information as well as useful route divergence information.

Many of our intersections lack signs or are otherwise unclear, so track your mileage or location.

Different routes intersect each other, so don’t assume that other riders are going your way.

Recovering from straying off course can add massive amounts of climbing to your ride. You can’t rely on your cell phone mapping to recover because there’s often no cell service. Around here GPS maps are often optimistic about which roads still exist so you can’t ride every road shown on their maps. Because of all that, staying on course can make your day much better, so please take care to do so. We do our best to help, but navigation is still a part of the challenge of the ride.


Equipment is a personal decision and self-knowledge is the only appropriate guide, but we’ll try to help. These suggestions are for all routes beyond the Family Ride and Green River Tour.

  • Most riders will require a bicycle with tires at least 30mm wide and very low gearing (a 1:1 ratio or lower).
  • You should be able to change your own flats and cut tires. Carry equipment to fix sidewall cuts and multiple punctures (a tire boot, patch kit, tubes, and pump or many CO2 cartridges).
  • Carry enough water to last you 30 miles uphill in whatever heat is forecast. If you use water bottles instead of a hydration pack, use bottle cages strong enough to retain your bottle over extremely rough roads, and retrieve your bottle if it does come out. Many riders get very excited on some descents, then very sad later about leaving their bottles behind.

Please choose your equipment conservatively because you’ll be riding in a rural area lacking bike shops and cell service, so if your bike breaks you may have a very long walk home (if you walk away from the break).

Riders complete the D2R2 on bikes ranging from mountain bikes to road bikes with 25mm tires to fat bikes, and the number of purpose-built gravel bikes grows each year.

What bike you choose should be based on the course you’re going to ride, weather conditions, and your experience riding dirt/gravel roads (read “roads” loosely for the longer routes as they include jeep tracks, discontinued roads, and trails).

Skill is more important than equipment. There is no bike that corners on loose gravel like on pavement. If you haven’t ridden gravel roads before please ride very carefully because the skill of riding on a loose surface takes experience to acquire.

Most riders on a road bike (tires narrower than 30mm) will walk some sections and need to descend extremely gingerly at points.

While some riders use carbon rims they are mostly disc brakes. Carbon rims have delaminated in the D2R2 from rim-braking heat.

Wider tires make for a far more comfortable long day in the saddle, and aren’t necessarily slower over the whole course. Mountain bikes with slicks or small knobs are quite competitive. However, drop bars provide more hand positions, which can help prevent sore hands.

Choose gearing that you can spin up a 16% grade seated (not standing) when you’re extremely tired. For most people this means at least a 1:1 ratio or lower, such as a 34-tooth chainring with a 36-tooth cog.

Deerfield Paved Road Randonnee riders will be able to complete the course on skinny-tired bikes.However, low gearing is highly desireable if the the option exists for choosing amongst avialable bikes (or switching out components on an existing bike).

A word of caution -If you make any custom alterations to your bike for this event, make them a week in advance and go for a test cruise.There is nothing worse than equipment failure 3 miles into the ride!

The Checklist


  1. Select Your Course
  2. Register
  3. Print your cue sheet
  4. Share this event with friends and family using Facebook, Twitter or E-mail
  5. Plan Your Visit (local lodging or camping options, and visit area attractions)
  6. Stay up to date with our Facebook page
  7. Browse media and commentary from other riders
  8. Check Start Times
  9. Get directions and arrive for breakfast before you start
  10. Have the ride of your life!
We couldn't do this ride without all the support from our hosts and local & international sponsors.  Please show them your support! 

Our current D2R2 Hosts and Sponsors

Celebrate & Share!
  1. Join us for the PRE-RIDE Party on FRIDAY with music, bonfire, beer and food.
  2. Indulge in our after-ride celebration with food, drink and fellow riders
  3. Send us your photos, videos, or blogs for the D2R2 community to enjoy
  4. Be sure to use #D2R2 across social media to join the conversation and share your photos! 

Smithsonian Cafe & Chowderhouse will be providing breakfast, lunch, and dinner for riders and Berkshire Brewing Company will be providing the post-ride beer.

Check back for additional Sponsors, Vendors and Food partners.


180K, 160K, 115K, 100K, and Mystery Ride.             

  • $100 Early Bird Registration (until December 31, 2019)
  • $120 Winter (January 1, 2020 - February 29, 2020)
  • $130 Early Spring (March 1, 2020 - April 30, 2020)
  • $145 Late Spring (May 1, 2020 - June 30, 2020)
  • $160 Summer (July 1, 2020 - August 9, 2020)
  • $180 on Ride Day (if space allows, after August 15, 2020)

Green River Ride 

Adults $80, $40 under 12 
Day of $100, $50 under 12

Family Ride 

Adults $40, $10 under 12
Day of $50, $10 under 12

Registration Headquarters opens at 5:00 AM 
Campers may register from 2-9 pm on Friday, August 14th 


Starting Times

180K  - 6:00 AM

160K -  TBD

115K - 8:00 AM

100K - 9:00 AM

Mystery Rides - TBD

40-mile Green River Tour - 10:00 AM to 11:00 AM

12-mile Family Ride (Registration and starting point for the Family Ride will be at a different location than the main headquarters!)  10:00 AM to 11:00 AM



The main Headquarters is located under a tent near the corner of Mill Village and Wells Cross Roads, approximately 1 mile south of the Village of Old Deerfield. Camping and parking are adjacent to event headquarters.


Planning Your Visit 

Camping |  Lodging |  Area Attractions

We provide a van for all riders to a hot shower within a couple of miles from the site. The van runs from 2pm - 8pm on Saturday. Our site is also adjacent to a wonderful swimming hole in the Deerfield River. Riders will need to bring their own towels, soap and shampoo.

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