The first two or three Festivals were run on the smell of an oily rag, and a lot of enthusiasm – Ted Woollan (President from 2014/2015)

Since 2012, the idea of holding a jazz festival in Central Victoria circulated among local and Melbourne musicians. Initially, Maldon was proposed as a suitable location with the support of the Mt Alexander Shire, but the event failed to gain sufficient interest. Castlemaine was then suggested by John Hannah and Ken Turnbull, the organisers of the local jazz jam, which had recently celebrated its 10th anniversary. They joined forces with Melbourne Jazz Jammers Ted Woollan and Colin Garrett to form a committee and launch the first Castlemaine Jazz Festival in 2014. With backing from the Shire Council, the festival was planned as a winter event over the Queen’s Birthday weekend in June, aimed at promoting tourism in the town.

The inaugural 2014 Castlemaine Jazz Festival featured performances across eight venues, including the popular ‘Jazz Train’ steam engine running from Castlemaine to Maldon and back. The venues included the Cumberland Hotel, Run Rabbit Run restaurant, The Bridge, The Public Inn, the New Northern Hotel (now the Northern Arts), Lot 19, and the Comma Hotel. The Five Flags in Campbell’s Creek was added in subsequent festivals. While some venues have changed over the years due to closures and private acquisition, newer locations have included the Theatre Royal, the Phee Broadway Theatre, Boomtown Winery at the Mill, the Town Hall, and the Bowls Club. The Coolroom at the Northern Arts Hotel is also a venue for 2023.

The first festival featured 58 bands across various jazz genres, including the Ade Ishs Trio, The Ruby Rogers Experience, and local bands like Vida Jazz and Moodswing. By 2016, the number of participating bands had grown to 104. Late-night jam sessions at the Comma (2014) and the Cumberland (2015) became popular, drawing both musicians and enthusiastic audiences. Positive feedback from attendees led to the decision to continue hosting the festival annually.

Over the years, the committee and presidency have evolved due to personal changes and other factors. Linda Carpenter served as President in 2017, followed by Calum McClure, who led the committee from 2018 to 2022. Run by volunteers and supported by sponsors, the Castlemaine Jazz Festival adapted to challenges like the COVID-19 pandemic, which affected the 2020 and 2021 events. However, a public outdoor concert was held in November 2021 to maintain interest. As of now, the festival is celebrating its twelfth edition since its inception in 2014.