The organization was founded in 1912 by a group of seven women including Cherilla Storrs Lowrey with the goal of beautifying Honolulu and opposing the use of billboards in Hawaii; members almost immediately began planting trees with the organization after its establishment, leading the program director to estimate in 2020 that the Circle had planted "tens of thousands of trees" across the state.

The Outdoor Circle was founded in 1912, initially under the auspices of the Kilohana Art League, by a group of seven women including Cherilla Lowrey.

[4] The Circle also established public fountains, parks, playgrounds, and gardens,[5] and emphasized the conservation of native trees and shrubs.

[8] In 2011, the Circle became one of the plaintiffs in a federal lawsuit aiming to halt an elevated rail system project for Skyline from going forward,[9] motivated by a belief that the rail would negatively affect approximately 900 trees and have an additional negative effect on the scenic views in Honolulu; former organization president Susan Spangler stated that "It’ll be so ugly".

After the organization created a mockup of a Joe Camel cigarette advertisement on a Honolulu bus, intending to point out that advertisements which are used now may be considered unacceptable in the future, then-Mayor of Honolulu Kirk Caldwell accused the Circle of "trying to create fear and misinformation" while Transportation Services Director Michael Formby described the mockup as "offensive [...] because [the Circle] knew we would never do that and yet they put out that press release.