The history of community gardening in North America has followed a boom and bust cycle; expanding in times of crisis only to retract when a feeling of security returns. This jarring cycle is facilitated by a view of community gardens as a temporary, pop-up, land-use. By framing gardens from the onset as ephemeral it is assumed that they will one day be replaced by a “higher and better use.” In order to break out of this cycle and have a permanent place in the urban geography it is imperative that models are developed that provide both long-term land security and can navigate the vicissitudes of community interest. In Chicago in the mid 1990s NeighborSpace was created in order to walk this difficult line. As Chicago’s only non-profit land trust dedicated to community managed open spaces, NeighborSpace provides long-term protection for more than100 vegetable, flower and prairie gardens across the City. The organization shoulders the responsibilities of property ownership so that community groups can focus on the business of gardening and organizing. This article takes a close look at two gardens secured in perpetuity by NeighborSpace.