Five-By-Five Ride Overview - 2017

"Be ready for anything and everything."

The Five-By-Five is a 500-mile adventure ride that covers every type of terrain.  Some of it crosses urban landscapes and some of it feels like you're a hundred miles from anyone. 

"Five-By-Five" stands for five-hundred miles throughout five States:  Massachusetts, Maine, New Hampshire, Connecticut, and Rhode Island.  The "states" are also likely to include:  sleep deprivation, confusion, exhaustion, hallucination, and maybe even jubilation.

Some riders are using this as training for the Tour Divide in 2017.  Some riders are doing the 5x5 as a mettle test.  Whatever your reason for making this ride, you won't forget your experience through every mile.

This ride is similar, in spirit, to events like the Coconino 250, the Cross Florida ride, and the Tour Divide.  One of the significant differences with the 5x5 is that it's supported - to some extent - so you're never too isolated while riding:

  •   Help is a phone call away.
  •   At each 100 mile campsite there's support for evening arrival and mechanical support.
  •   We provide a comprehensive rider's booklet that has details about provisions, bike shops, food, and sleep stop options.

When:  September 7 - 11, Thursday through Monday, 2017.  Start time:  5:00 am

Where:  Starting and ending in Massachusetts, near Boston.

What:  The most diverse riding experience you may ever have.

Why:  This is a ride like no other - of which we're aware.  This is definitely the longest and most challenging multi-day mixed-terrain event in New England.  Be a part of history for this first official riding of the Five-By-Five!

How:  Register at Bikeregregistration is open now.  We hope you'll join us for this life altering event.


  • Early Registration:  January 1 - July 6:  $445
  • Final Registration:  July 7 - September 4:  $645

Questions?  Email us at Overland Base Camp.

Ride Statistics

  • Time Limit:  Six days or 144 hours
  • Distance:  About 500 miles
  • Ride Type:  Extremely mixed-terrain.  This ride has just about every type imaginable - from perfect pavement to full-on mountain biking.  40% dirt; 60% pavement.
  • Elevation Gain:  About 35,000 feet
  • Territory:  Ranges from deep woods to urban centers.
  • States Visited:  Massachusetts, Maine, New Hampshire, Connecticut, and Rhode Island.

The Fine Print

All details subject to changes.  All additions and improvements to the 5x5 will be posted here, and once you've registered for the event you will receive fortnightly email updates.

In addition to the entry fee you are also required to have a dedicated GPS device, lights for night riding, and a SPOT Tracker.  We can rent you a SPOT or you can purchase one.

What you get for that price:  This ride asks for a lot.  In return, we offer a lot.

  • Support:  Neutral support throughout the ride.
  • Camping:  We have campsites reserved and paid for at each 100-mile point.  We're congregating each evening to share stories from the road and trail.  You carry your gear and we'll have a legal spot reserved for you.  See the 5x5 Rules Page for details.
  • Meals:  On Thursday morning before the Grand Depart.  On Monday evening after the official finish.
  • Route:  GPX files of the entire route.  Overland Base Camp has a reputation for amazing routes.  The Five-By-Five will not disappoint.
  • Accomplishment:  Do something very few people have ever done:  500-miles of mixed terrain.
  • Prepare for Tour Divide:  We don't know of another event that will better prepare you for Tour Divide 2017.
  • Custom T-Shirt or Cap:  Custom commemorative Five-by-Five linen cap or custom tailored t-shirt included in entry fee.  A $45 value.

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