Ride Info

What’s Included

Included in your registration

  • Checkpoint foods to include grab and go, pocket-friendly fruits, snacks, bars, and, of course, water and electrolytes
  • Lunch at about the halfway point to include more robust offerings
  • Dinner served from 2–8:30 pm. Dinner will be served under the big tent as in past years.
  • A free pint of beer 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

The Ride

Every route is beautifully scenic and includes significant climbing and descending, with its physical and technical challenge.

  • 180k
  • 160k
  • 105k
  • 100k (the original is back!)
  • 40-mile Green River Tour
  • 12-mile Family Ride
  • and an annual Mystery Ride!

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

Route descriptions

Rules of the “Road"

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, do not impede traffic 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.

In Massachusetts and Vermont, the law states:

(1) Bicyclists riding together shall not ride more than 2 abreast but, on a roadway with more than 1 lane in the direction of travel, bicyclists shall ride within a single lane.


Rest Stops

Rest Stops

There will be checkpoint rest stops supplying water and food at least every 30 miles (usually every 20). There will be a robust lunch around the halfway mark 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 as we get closer to ride day.

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.

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

The Checklist


  1. Select Your Route
  2. Register
  3. Print your cue sheet
  4. Share this event with friends and family using Facebook, Instagram, 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. Check Start Times - they will be finalized as we get closer to the ride. This year we will have staggered starts.
  8. Get directions and breakfast before you arrive.
  9. Have the ride of your life!


Fee Schedule

180K, 160K, 105K, 100K, and Mystery Ride  (Includes breakfast, lunch, dinner, and rest stops)

  • $150  Early Registration (until December 31, 2023)
  • $175  January 1, 2024 - March 31, 2024
  • $200  April 1, 2024 - June 30, 2024
  • $225  July 1, 2024 - August 4, 2024
  • $250 on Ride Day (if space allows)

Green River Ride (Includes breakfast, lunch, dinner, and rest stops)

  • $100 Early Registration (until December 31, 2023) -   $50 for riders under 18
  • $125 January 1, 2024 - June 30, 2024  - $50 for riders under 18
  • $150 July 1, 2024 - August 4, 2024 - $50 for riders under 18
  • $175 on Ride Day (if space allows) - $50 for riders under 18

Family Ride (Includes lunch and dinner)

Adults $50, $10 under 12



The humor is that our starting tent has no address... it is in a field about 1 mile south of Historic Deerfield, ¼ mile west of US Route 5.

If you're using GPS...

Try using the intersection of Mill Village Rd and Wells Cross Road, Deerfield, MA.

We will have a huge tent set up in the field, and there will be D2R2 signs up as you approach Old Deerfield.

For the traditional direction-takers...

From the South
Take I-91 North to Exit 24 (Deerfield); take a right off the ramp onto US Route 5 North; 4.5 miles later, go left onto Wells Cross Road; at the end of the street, turn right onto Mill Village Road and proceed to the parking area (just after our tent).

From the North
Take I-91 South to Exit 26 (Greenfield - Route 2); go halfway around the traffic circle and get off onto Route 2A East; go right at the second light (Dunkin' Donuts) onto River St; at the next light, go right onto US Route 5 South; 4.3 miles later, turn right onto Wells Cross Road; at the end of the street, turn right onto Mill Village Road and proceed to the parking area (just after our tent).

From the Village of Old Deerfield
Proceed south on Old Main Street; at the end of the historic district, fork right onto Mill Village Road; about a mile later you will see our tent. There will be a parking area just before our tent.

Our 2024 Sponsors

We couldn't do this ride without all the support from our hosts and local and international sponsors.  Please show them your support!