When professional bike racer and bike shop owner, Fred Kugler, now universally known as "Pop," decided to promote a bike race in his small New Jersey hometown of Somerville, he encountered one problem. New Jersey state law prohibited racing on highways for prizes, and Somerville's Main Street doubles as State Highway 28. To bypass this legislation, Kugler then decided to name the race a "tour," and the 50-mile Tour of Somerville was born in May of 1940.

Kugler's son Furman, a past National Cycling champion and one of the country's most promising cyclists, won the inaugural Tour of Somerville in 1940 and repeated his victory in 1941. Carl Anderson, a friend of the Kuglers’ won the Tour in 1942. World War II suspended the Tour from 1943-1946 and its Memorial Day date took on a sad irony when Kugler and Anderson were both killed while serving with the Armed Forces overseas. Resuming in 1947, the Senior Men's race of the Tour of Somerville was officially renamed the Kugler-Anderson Memorial, in honor of the two past winners who gave their lives for their country.

The perpetual tour trophy, "The Cromwell Cup," was donated back in 1940 by the Canadian government. James Cromwell, US minister to Canada, was Doris Duke's husband.

Every conceivable item has been awarded as prizes (along with the coveted trophy). Household furniture, appliances, carpeting and even a brand new Chevrolet in 1953 have been given to winners.

In 1955, Patrick Murphy, a 21-year-old bridegroom from Ontario, Canada, took time off from a honeymoon tour of the states to win the Tour and set a new record of 2 hours, 2 minutes.