Roadsides contain promising habitat for insect pollinators, yet roadside restorations can be expensive and are rarely evaluated for effectiveness. Where do we establish pollinator-friendly revegetation to maximize benefits? How effective are current revegetation practices at providing habitat for pollinators? We address these questions with two studies. Chapter 2 examines the impact of roadside-adjacent habitat that has been identified as pollinator-friendly for bumble bees. We use pollinator habitat maps to examine associations between the amount of nearby pollinator-friendly habitat and bumble bees (abundance and richness). We also regroup land covers to more specifically align with bumble bee habitat needs and compare the ability of both land cover categorizations to predict bumble bee metrics. This study can help refine predictors in mapping efforts to prioritize locations for pollinator habitat enhancements. Chapters 3 and 4 combine detailed insect and floral surveys of sites with known revegetation history to test efficacy of current revegetation methods for providing habitat for insect pollinators. We show which plants establish after seeding and how communities change as they age. We find that native flowering plants are more likely to establish in roadsides when they are planted, but native and non-native seeded sites converge in the plant community through time. Bumble bee and butterfly abundance and diversity is tied to flowering plant abundance and diversity, regardless of their status as native plants. This work identifies where pollinator-friendly restorations should be implemented and how current seeding practices could be modified to improve benefits to pollinators while reducing costs.