As landscape fragmentation continues to escalate, it is imperative that we improve our understanding of the factors that contribute to the creation and retention of forest on privately-owned land to most effectively design and implement conservation policy. This article presents the percentages of variation in the proportion of forest on private ownerships across an agriculturally-dominated landscape in north-central Indiana, USA that can be explained by biophysical characteristics, landowner (socioeconomic) attributes, and private landowner assistance programs. While biophysical characteristics of the land accounted for the majority of variation explained (17.35%, p < 0.0001, n = 194), attitudinal and demographic attributes of the landowners contributed significantly to explaining additional variation (7.97%, p<0.0001), and overlapped with biophysical characteristics to explain another 17.31%. Program familiarity and enrollment did not explain a significant amount of the variation independent of either biophysical or landowner attributes. Private landowner assistance programs should broaden their objectives and increase incentives to appeal to the variety of landowners who possess the decision-making authority for most of the land in the region and the nation as a whole.