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Studies suggest that urban form can influence microclimate regulation. Remote sensing studies have contributed to these findings through analysis of high-resolution land cover maps, landscape ecology metrics, and thermal imagery. Collectively, these have been referred to as land cover configuration studies. There are three objectives to this study. The first is to assess the relationship between nighttime land surface temperatures (LST) and land cover configuration and composition. The second objective is to outline a comprehensive methodology that includes ordinary least squares (OLS), spatial regression, variable selection, and multicollinearity analysis. Our last objective is to test three hypotheses about the relationship between LST and land cover, which can briefly be described as: 1) the importance of land-use regimes in modeling LST from land cover composition and configuration variables; 2) the strength of the correlation between LST and roads, buildings, and vegetation; and 3) the improved quality of models using landscape metrics in modeling the relationship between LST and land cover. Based on 16 different models (8 OLS, 8 spatial regression) we could confirm the above hypotheses, but we found that the configuration of buildings, roads, and vegetation have a complex relationship with LST. Our interpretation of this complexity, combined with the strength of composition variables, is that parsimonious models, for now, are more useful to urban planners because they are more generalizable. Finally, spatial regression models of land cover configuration and LST demonstrated an improvement over non-spatial linear models (OLS). Spatial regression models reduced heteroskedasticity and clusters of residuals, and tempered coefficients, suggesting that the OLS models could be biased. OLS models were still found to be a valuable tool for exploratory analysis.