PlumFest was first hosted in May of 2015. It began as an idea island residents and musicians Kevin Kelley and Cynthia Keefe had about Plum Island as a music destination. They created PlumFest to bring together all the local musical talent that was in abundance and sought to establish Plum Island as a musician’s destination community.

Kelley and Keefe continued organizing PlumFest each subsequent year on the third weekend of May from 2015 to 2019, growing the number of bands and hosts year over year and increasing the buzz of the event. It soon became the favorite annual event of most Plum Islanders and a destination event for musicians and music lovers in the Merrimack Valley area and beyond.

In 2020, Kelley and Keefe made the difficult decision to call off PlumFest due to the surge of the CoronaVirus Disease. They resumed operation of the event in 2021, moving PlumFest to the third weekend in September and handing over most of the responsibilities to a new team led by Linda McKeehan, who volunteered to helm the event and provide continuity when the founders stepped down.

Kalpesh Desai incorporated the event in October 2021 and became President of PlumFest Charitable Trust, Inc., with McKeehan as Secretary. No directors were appointed. McKeehan and Desai led the organizing team in 2022 with Shannon Kinney and Mary Ellen Powers assuming key event management and marketing roles.

In 2023, Powers and Kinney led the PlumFest team with McKeehan staying on as financial manager. The September 2023 event was canceled due to the public safety concerns of Hurricane Lee’s impact on Plum Island; and thus, the organizers instituted a Rain Day Policy to begin in 2024. (Note: organizers salvaged the day by pivoting to a “Plan B.” With the cooperation of the island’s two restaurants with entertainment capacity, a full slate of bands was scheduled at each; the following day the sun appeared and several hosts proceeded with musical performances that were publicized. Attendance was significant, and resulted in Plan B raising nearly half of anticipated donations had the full event gone on.

Each year from 2015 to 2023, a beneficiary was selected, and proceeds of the event were presented to the beneficiary in a ceremony in October. These beneficiaries have included the Newburyport Youth Services, the Merrimack River Watershed Council, and the Boys and Girls Club of Lower Merrimack Valley. Certain years’ fundraising proceeds were also allocated to music scholarships for local youth. The Boys and Girls Club has been able to build a music education room significantly supported by the proceeds of PlumFest, and they in turn have provided volunteers for the PlumFest event every year.

The PlumFest Charitable Trust was re-established in January 2024 with new corporate officers and directors as well as formalized plans for selecting beneficiaries and attracting sponsors.