Organized pickleball began in the Champlain Islands in July 2016 in partnership with the North Hero Recreation Committee and the North Hero Elementary School. Two pickleball courts were laid out and lines taped on the basketball court behind the school. Interest in pickleball grew quickly and in 2017 the North Hero schoolyard courts were expanded to three courts.

In order to achieve its mission throughout Grand Isle County, expansion continued with three pickleball courts at the Grand Isle Recreation Park on Donaldson Road in August of 2019, two courts at the Veterans Park in Isle La Motte in June 2020, and two courts behind the Islands in the Sun Senior Center in Alburgh in late 2020. In all cases, these expansions made use of existing paved surfaces and the painting and lining of the pickleball courts and purchase of nets and balls were funded through nominal IPA membership fees.
Pickleball participation in the Islands has grown every year since it began in 2016. The chart below illustrates the total number of two-hour sessions (includes training, tournament, and recreational sessions) and the total number of players who participated.

The Islands Pickleball Association, Inc., a Vermont based nonprofit, was incorporated in July 2019 and was approved by the IRS as a 501(c)(3) association.