Brattleboro, Vermont · Sunday, August 16, 2026
The Retreat Farm Ramble is a cycling and gravel event held on Sunday, August 16, 2026. It is located at 45 Farmhouse Sq in Brattleboro, Vermont.
The Greenfield Triathlon is the longest running triathlon in New England!
Situated in the heart of Franklin County, the Greenfield Triathlon course meanders through the picturesque back roads of Greenfield, passes through the Historic Eunice Williams Covered Bridge, and features swimming in our very own Green River.
Offering both International and Sprint distances for individual athletes as well as two- and three-person teams, the Greenfield Triathlon is great for both beginners and seasoned triathletes. A triathlon training program is offered Sundays leading up to the event. In Greenfield, our motto is “To Finish Is To Win!”
All race proceeds benefit the Greenfield Recreation Department. The Greenfield Triathlon has raised thousands of dollars to support programs and events for families within our community. We thank you for your continued support.
Next in the Pedal2Pints Social PopUp ride series!
Revisiting the easy, scenic, classic route between two of the newer P2P-supporter breweries. We will start in Greenfield near Four Phantoms Brewing; head North to Bernardston (approx 6 miles) for a beverage (beer, seltzer, and NA available) at Incandescent Brewing; then return to Four Phantoms (approx 8.5miles) for more merriment (beer, mead, ciders, NAs all available) and snacks.
Registration includes 1 beverage at each brewery and a food item back at Four Phantoms.
Additional food and beverages available a la carte.
D2R2 - The Deerfield Dirt Road Randonnée 2026
RIDE FOR THE LAND
Saturday, August 22, 2026
Presented by the Franklin Land Trust
We celebrate the landscape, the history, and the rural culture of western Massachusetts, and work to ensure, through a program of land protection, that the historic pattern of field, woodland, and village will endure for the benefit of generations to come.
Rain or Shine Event - Sorry No Refunds
ROUTE CHOICES (see descriptions)
180K (the OG route that started it all!)
160K (New portions for 2026)
105K to Rowe
100K (the Original!)
92K (with a 77K option)
80K Point-to-Point Ride (New for 2026!)
36-mile Green River Tour (customizable from 36 to 52 miles)
12-mile Family Ride
Register early for the best rates.
New Starting and Finish Location!
With the continued growth of the event and the desire to offer even more potential fun into the future, we have made to decision to move the D2R2 headquarters to the Franklin County Agricultural Fairgrounds on Wisdom Way in Greenfield, MA.
CAMPING - Our new location offers an expanded on-site camping area with water, electricity, and pump out station. Bathrooms and showers are adjacent to the camping area. (Just bring your guitar, firepit and S'mores to make the experience complete!)
PRE-RIDE PARTY - FRIDAY EVENING - Friday night will bring a lively, welcoming atmosphere with new food trucks, music, and games! Plus, celebrate our 21^st birthday at our brand-new beer garden! Bring friends and family to gather with the D2R2 community before the ride to kick off the festivities.
Keep an eye out for exciting updates in the weeks ahead!
CHOOSE YOUR ROUTE
180K, 160K, 105K, 100 K, 92K (Breakfast, lunch, dinner, and rest stops provided - see: What’s Included)
$150 Early Registration (until December 31, 2025)
$175 January 1, 2026 - March 31, 2026
$200 April 1, 2026 - June 30, 2026
$225 July 1, 2026 - August 9, 2026
$250 on Ride Day
80K Point-to-Point (Transportation to stating location, plus breakfast, lunch, dinner, and rest stops provided - see: What’s Included)
$230 Early Registration (until December 31, 2025)
$255 January 1, 2026 - March 31, 2026
$280 April 1, 2026 - June 30, 2026
$305 July 1, 2026 - August 9, 2026
$330 on Ride Day
Green River Ride (Breakfast, lunch, dinner provided - see: What’s Included)
$100 Early Registration (until December 31, 2025) / $50 for riders under 18
$125 January 1, 2026 - June 30, 2026 / $50 for riders under 18
$150 July 1, 2026 - August 9, 2026 / $50 for riders under 18
$175 on Ride Day / $50 for riders under 18
Family Ride (Lunch and dinner provided - see: What’s Included)
Adults $50, $10 for riders under 12
Visit us on Facebook facebook.com/fltrust and Instagram instagram.com/fltrust
for up-to-date information about D2R2
Be sure to use #D2R2 across social media to join the conversation and share your photos!
General Information
Ride Info (All the Important Stuff)
Plan Your Visit (Camping, Lodging, Directions)
Raffle
Routes (descriptions, maps, cue sheets)
Volunteer
Sponsorship
Past media
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 its 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 the routes
The event is a key fundraiser for the Franklin Land Trust's efforts to preserve land in the region.
QUESTIONS?
Registration & Franklin Land Trust questions: email Mary [email protected]
All other questions: email Sandy - [email protected]
D2R2 Event Headquarters and starting point
The event headquarters will be held at the Franklin County Agricultural Fairgrounds on Wisdom Way in Greenfield, MA.
The starting location and finish line, registration, food and beverages, music, Friday night party, showers, bathrooms, camping and parking areas are all within the fairgrounds gates!
Bring the entire family!
Area attractions for non-riders include Historic Deerfield,
PVMA's Memorial Hall Museum and Indian House, Shelburne Falls,
Yankee Candle, Art Galleries and so much more.
We plan to offer a free mini D2R2 for our very youngest riders right inside the Fairgrounds! Bring their trikes and bikes. Watch for more details to come!
Who is the Franklin Land Trust (FLT)?
FLT is a 501(c)(3) devoted to the conservation of farm and forest land, and the rural character of western Massachusetts. FLT helps farmers and other landowners protect their land from unwanted development. To date, FLT has helped to preserve over 32,000 acres of open space. The hills and valleys of the region—with their farms, sugar bush, rambling old New England roads, and small towns steeped in history—are a unique and precious resource that D2R2 riders will experience at every turn in the road.
Contributions to the Franklin Land Trust allow us to continue our efforts to protect this invaluable resource and are tax-deductible.
Please visit our website www.franklinlandtrust.org for more detailed information about road conditions and training for this event.
For complete information and ride photos please go to: d2r2.franklinlandtrust.org
Race Date: August 29,2026
Race Time: 9:30 AM (Fun Run @ 9:00 AM)
Bib/Shirt Pick Up and Race Day Registration: 8:00-9:15 AM
For generations, Dublin Christian Academy Stags have been running “the loop" a legendary training run that has become a rite of passage for our athletes (see course map below). This year, you can test your mettle on the same course that has honed our champions at the inaugural Stag Stampede 5K and Fun Run. Join us to run, walk, or push the kids in the stroller. Stay for post-race refreshments sponsored by DCA Parent Connect. All proceeds from this community 5K will benefit the Dublin Christian Academy athletics programs: DCA Stags soccer, volleyball, and basketball.
Prices: $25 Early Bird Special thru Jul. 31, 2026
$30 Aug 1 thru Aug. 27, 2025 (6:00 P.M.) Race Day Registration $35
Fun Run (.25 mile) FREE (no shirt)
We look forward to cheering all our runners & walkers on August 29,2026!
**Race Shirts guaranteed by August 7th.
Note for 5k Course: Known among DCA athletes as “the loop,” the scenic, single-lap 5K course begins at the playground on the school’s main campus on Page
Road. The course begins mostly flat and runs south down Page Road, turns east (left) on Craig Road, north (left) on Route 137, west
(left) on Windmill Hill Road where the elevation gradually rises, and finally, south (left) on Page Road up Alsi’s Hill, west (right) on
the dirt loop beyond the playground, north (left) back on to Page Road, and ends back at DCA’s playground. This gently rolling, open-road course has a mix of paved road and gravel.
Note for our Fun Run: We have a beautiful quarter-mile fun run begins at the DCA playground and follows the dirt drive past the shop, then turns south (right) onto
the dirt drive that leads to the field cottage with a view of Mount Monadnock on the right. The course continues east (left) up Carriage
Path (grass path between the stone walls) and then turns north (left) at the gate onto Page Road, ending back at the playground
If you are interested in volunteering or sponsoring this event please contact Tracey Burt - [email protected] for more information.