In an interview before his death in 1990, Pop recalled that “Furman wanted to sleep in his own bed for a change the night before a race, so I figured ‘why not, let’s give people something to look at.’” The elder Kugler got the necessary licenses and sanctions from cycling officials in 1939 but the one thing he didn’t count on was a snag from the state capital.

“I wanted to call it a race,” he said some years later, but New Jersey law specified that no contest of any type for wage, purse, or prize could be held on a state highway.

Furman sat out the 1942 event and that opened the door for one of his closest friends, Carl Anderson of Clifton, New Jersey, to take top honors.

Given advances in bike technology and the physical evolution of competitive cyclists, recent winning times for the race have been approaching the 1 hour and 40 minute mark.

For his efforts during the inaugural race, Kugler won a new bicycle valued at $75, a trophy, an oil painting and a badminton set, a far cry from the current $20,000 in total prizes, distributed in equal $10,000 purses for the top men and women finishers.

[10] Several of the winners of the Harry Naismith Junior event also won national championships during their cycling career: Jackie Simes,[11] Bobby Fenn,[12] Alan Grieco,[12] Roger Young,[13] Bruce Donaghy,[14] Andy Weaver,[15] Dale Stetina,[16] Jeff Lippincott,[17] David Brinton,[18] Ken Christoff.

[19] Many of these riders also competed at the Olympics, Pan-American Games, and/or World Championships (Jackie Simes, Roger Young, Bruce Donaghy, Andy Weaver, Dale Stetina, David Brinton).

Mildred, daughter of race founder Fred “Pop” Kugler, was herself a New Jersey state champion who won the 1940 national cycling championship in her category.

[24] In 1980, Sports Illustrated published a six-page photo feature story on the race headlined “The Somerville Whirl,” in which author Sarah Pileggi concluded: “As for the spectators, at the cost of not one penny and from the best location in the house, the sidewalks, they will be able to watch the world’s finest athletes whirring past on their delicate machines 77 separate times.

Recent changes to the Tour's course have shortened the length of a lap by several blocks to move the start finish line to the heart of the town's commercial Main Street.

Regarding the change, Jackie Simes, former Olympian and two-time winner of the Tour, has said, “It makes racing a little more technical from the riders’ perspective, which is good.

It's a harder turn to make on to Bridge Street, I remember being smack up against the curb because it funnels down in there; it's a great place to watch the race.