Increasing non-crop plant diversity promotes desirable environmental and economic outcomes on farms. For example, elevated non-crop plant diversity can support biodiversity at other trophic levels, enhance ecosystem services, and reduce weed–crop interference. Barriers to increasing non-crop plant diversity include logistical issues and competition from dominant weed species. This dissertation comprises four studies focused on overcoming these barriers. Chapter 1 is a scoping review of the relationship between agricultural management and weed diversity within crop fields. It describes a small but rapidly growing body of research, mostly performed in temperate field cropping systems. Priority areas for future research include weed seedbanks and functional diversity. Chapter 2 reports on Multi-Seed Zea Pellets (MSZP), a novel technology that enables planting of small, irregularly shaped seeds using conventional field crop planters. Greenhouse and outdoor pot experiments demonstrated successful establishment of common milkweed (Asclepias syriaca) from MSZP. This approach could be used to plant morphologically diverse seed mixtures near or within crop fields. Chapter 3 is a two-year, two-site field experiment focused on perennial flower strips established with minimal weed control. These flower strips were dominated by weeds recruited from the soil seedbank, especially in the first year. By the second year, high densities of black-eyed Susan (Rudbeckia hirta) contributed to increased pollinator abundance. Chapter 4 is a one-year experiment conducted on five commercial farms. The experiment involved annual flower strips, which may be a suitable approach when perennial flower strips are not feasible. Annual flower strips increased biodiversity, even when seeding was delayed until early summer. Several of the seeded annual flowers competed well against weeds. Overall, these four projects demonstrate that efforts to promote non-crop plant diversity are inherently complex. Numerous constraints can hamper these efforts. At the same time, this research shows that management practices supporting non-crop plant diversity are both feasible and beneficial on farms. Emerging tools will make these practices more widely accessible.