Scenario planning is a powerful approach for assessing restoration outcomes under alternative futures. However, developing plausible scenarios remains daunting in complex systems like ecological communities. Here, we used Bayesian multispecies occupancy modeling to develop scenarios to assess woodland restoration outcomes in afforested communities in seven wildlife management areas in Arkansas, U.S.A. Our objectives were (1) to define plausible woodland restoration and afforestation scenarios by quantifying historic ranges of variation in mean tree cover and tree cover heterogeneity from 1986 to 2021 and (2) to predict changes in bird species richness and occupancy patterns for six species of greatest conservation need under two future scenarios: complete afforestation (100% tree cover) and woodland restoration (based on remotely sensed historic tree cover). Using 35 years of remotely sensed tree cover data and 6 years of bird monitoring data, we developed multispecies occupancy models to predict future bird species richness and occupancy under the complete afforestation and woodland restoration scenarios. Between 1986 and 2021, tree cover increased in all study areas—with one increasing 70%. Under the woodland restoration scenario, avian species richness increased up to 20%, and four of six species of greatest conservation need exhibited gains in occupancy probability. The complete afforestation scenario had negligible effects on richness and occupancy. Overall, we found decreasing tree cover to historic levels prior to widespread afforestation would provide community-level benefits and would do little harm even to forest-dependent species of conservation concern. Applying multispecies occupancy modeling within a scenario planning framework allows for comparing multiscale trade-offs between plausible futures.