Overland Base Camp has an ever expanding array of rides that embrace terrains and challenges of all kinds.

We manage rides ranging from 17-mile fun excursions like the Short Diverged all the way up to the most arduous seven-day Five-By-Five mixed terrain bikepacking ride, and everything in between. 

If you're interested in a ride that includes testing your mettle and riding in unusual ways, we hope you'll find something here of interest.


Calendar for 2017

DateEvent &
Registration
TypeDistance, EstimatedLocation & Details
Rain Dates TBD
Diverged
- - - - - - -
Register Here
Mixed-Surface16 miles, 38 miles & 46 milesStarts in Lexington, Massachusetts
- - - - - - -
Overland Base Camp's funnest ride! Departing from Ride Studio Cafe 2016 overview here.
August 26, 2017
Saturday
Honey 100
- - - - - - -
Register Here
Mixed-Surface Exurban50km, 100km, & 100 milesStarts in Sherborn, Massachusetts
- - - - - - -
A new version and additional location for the perennial favorite mixed-terrain ride.
September 7 - 11, 2017
Thursday - Monday
Five-By-Five
- - - - - - -
Register Here
Mixed-Surface Exurban & Rural500 miles over 5 daysStarts in Sherborn, Massachusetts
- - - - - - -
Trekking through five states in five days. All terrain. The toughest cycling event in New England.
October 14, 2017
Saturday
The Formidable
- - - - - - -
Register Here
Two Versions: 100% Paved or Mixed-SurfacePaved: 160 miles & 100 miles
Mixed: 120 miles
Starts in Franklin County, Massachusetts
- - - - - - -
The toughest single day ride in Massachusetts. Love to suffer. 2015 report here.

Calendar for 2018

DateEvent &
Registration
TypeDistance, EstimatedLocation & Details
January 20, 2018
Saturday
All Conditions RideMixed-Surface, dirt roads, pavementAbout 25 milesStarts in Lexington, MA
- - - - - - -
Looking for all the mixed-terrain conditions that winter has to offer.
February 10, 2018
Saturday
Wintertide RideMixed-Surface All-Weather90 miles, 60 miles, & 45 milesStarts in Worcester County, MA
- - - - - - -
Embracing winter in a mixed-terrain fashion.
April 28, 2018
Saturday
DigressionMixed-Surface23 miles & 45 milesStarts in Sherborn, Massachusetts
- - - - - - -
Overland's most primordial ride, come see the hidden paths, abandoned routes, and primitive trails. Departing from Ride Headquarters
May 19 & 20, 2018
Saturday & Sunday
Maneha 250Mixed-Surface Exurban & Rural250 miles over 2 daysStarts in Lexington, Massachusetts
- - - - - - -
60% dirt; 40% pavement - all ridden within 48-hours.
June 29 - 30, 2018
Saturday overnight into Sunday
Dusk to Dawn RideMixed-Surface90 milesStarts in Sherborn, Massachusetts
- - - - - - -
We're riding throughout the night; warm fire included.
July 20 - 22, 2018
Friday - Sunday
Nomad 3-dayMixed-Surface RuralAbout 50 miles each dayStarts in Sherborn, Massachusetts
- - - - - - -
Three days of riding and two days of camping. Breakfasts and dinners provided.


Events We Help

  • Coffee Cross:  A ride we've done in different forms since 2011.  A ride that gets us ready for the cyclocross season.
  • Highpoint Ride:  This three-day fully supported road ride pulls participants to the highest point in Massachusetts:  Mount Greylock.

Events That Inspire Us

Events To Which We Aspire