Declines among species of insect pollinators, especially butterflies, has garnered attention from scientists and managers. Often these declines have spurred governments to declare some species as threatened or endangered. We used existing presence–absence data from surveys for the threatened Dakota skipper Hesperia dacotae (Skinner) to build statistical maps of species presence that could be used to inform future monitoring designs. We developed a hierarchical Bayesian modeling approach to estimate the spatial distribution and temporal trend in Dakota skipper probability of presence. Our model included a spatial random effect and fixed effects for the proportion of two grassland habitat types: those on well-drained soils and those on poorly drained soils; as well as the topographic slope. The results from this model were then used to assess sampling strategies with two different monitoring objectives: locating new Dakota skipper colonies or monitoring the proportion of historically (pre-2000) extant colonies. Our modeling results suggested that the distribution of Dakota skippers followed the distribution of remnant grasslands and that probabilities of presence tended to be higher in topographically diverse grasslands with well-drained soils. Our analysis also showed that the probability of presence declined throughout the northern Great Plains range. Our simulations of the different sampling designs suggested that new detections were expected when sampling where Dakota skippers likely occurred historically, but this may lead to a tradeoff with monitoring existing sites. Prior information about the extant sites may help to ameliorate this tradeoff.