The Greenfield Music Festival started as the Greene Countrie Towne Festival in 1967, when the main feature was an antique and classic car show. The group responsible for that car show was the Greenfield Antique Car Club, a group that is still active in 2023. In the early days, other organizations such as the Greenfield Jaycees, Lions, and Rotary clubs sponsored other activities, such as the Rotary Club’s putt-putt booth. Over time, the festival became more organized, with a committee and the name Greene Countrie Towne Festival. The name is based on a description of Greenfield by its founder, Gen. Duncan McArthur, who used the old English spelling in describing Greenfield as a "Greene Countrie Towne," which hearkens back to Greenfield's rich history dating from its founding in 1799.
Through the 1970s, the festival grew quite large and became a three-day and even four-day event. The peak year for the Greene Countrie Towne Festival was 1985, which featured many additional events and attractions, including hot-air balloon rides, a demonstration by Frisbee-catching dogs, and even a souvenir program. The 1985 Greene Countrie Towne Festival attracted huge crowds, but lost money. In 1986, the festival’s featured event was a rodeo, and staging that was rather expensive. Then the unthinkable happened on the third weekend of July when thunderstorms rolled through the area and spoiled the attendance.
As a result, the festival suffered a great financial loss, and the committee shut down, unable to pay the costs of putting on the rain-soaked festival. In 1987, when it became apparent that there would no longer be a Greene Countrie Towne Festival, the Greenfield Rotary Club stepped up and put on a one-day festival utilizing all-volunteer entertainment and a very simple format. After a few years, the festival was expanded to three days and was given the name "Wheels of Progress Festival." The Greenfield Rotary Club continued to sponsor the event, and it has grown over the years to about the same size as the original Greene Countrie Towne Festival. In 2011, the Greenfield Rotary Club changed the name of the festival back to the Greene Countrie Towne Festival, as the community festival was known in the 1970s and 1980s before going defunct after the 1986 festival.
After 35 years of sponsoring the Greene Countrie Towne Festival, the Rotary Club of Greenfield decided to step down from the role of festival sponsor in October 2022. After a meeting of local community members and business owners, it was decided that the festival needed to continue, and then came the birth of a new organization. In November 2022, a new non-profit organization was officially formed, incorporating in January 2023. After several meetings and discussions about the changes that needed to be made to ensure the success of the new organization taking over the festival, the Greene Countrie Towne Festival was officially changed to the Greenfield Music Festival. When asked why the name was changed, the committee said that they wanted to honor Greenfield's musical roots. Aside from a name change, the date was also changed to the first full weekend in June.
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