The race was the idea of Tommy Leonard, an avid runner and popular bartender in Boston and Falmouth.

One year later, in the summer of 1973, with the help of the town's recreation director Rich Sherman, and a local high school track coach John Carroll, the first Falmouth Road Race was run by approximately 100 people.

Five runners, celebrated through the years as "The Falmouth Five" Mike Bennett, Tom Brannelly, Don Delinks, Ron Pokraka and Brian Salzberg, have officially completed 46 consecutive Falmouth Road Races.

The beginning of the course is extremely hilly, with a starting line by the Captain Kidd Restaurant & Bar in Woods Hole, and a finish by the Falmouth Heights beach.

From the start corral, one races up a gradually steepening incline and into a narrow wooded road, emerging onto a long curved coastal stretch that runs by Nobska Light, continuing along a wooded road with gentle rolling hills, emerging onto Surf Drive along a hot beach on Martha's Vineyard Sound, past beach cottages on stilts, before turning inland toward the center of Falmouth town, along Falmouth Harbor, and finally looping back to the shore route for one last 1⁄4-mile (400 m) hill that crests just before the finish.