The tour was started in 1962 by Charles and Greg Siple, a father and son, and grew from there to become one of the largest bicycling tours in America, having 2,672 riders in 2010. The most riders the tour ever hosted was in 1989 with 6,650 riders. A staggered start was necessary beginning in 1973 when the tour reached 2,500 cyclists. People come from all over the nation and Canada to ride TOSRV. Charlie Pace was named director of the tour in 1967 and retired after the 50th anniversary ride in 2011. The tour is now an important part of the culture in Portsmouth, which is known as the city of murals for the colorful depictions of its history on the flood walls. One of the murals is a depiction of the tour.