Alfalfa is an important forage crop in North America, and it can also be found as a roadside weed in alfalfa-growing regions. Weediness and invasiveness are greatly facilitated by establishment ability, yet little is known about the ability of alfalfa to establish in competitive environments such as roadsides. The primary objective of this study was to estimate the degree of alfalfa establishment without managed cultivation under different seed-dispersal times and disturbance regimes. The study had a split-plot design with two main plots (spring and fall seed dispersal) and five subplots (mowing, soil disturbance, herbicide spray, seedbed, and undisturbed control). The study examined establishment, growth attributes, and reproductive output of alfalfa in response to these treatments. Alfalfa establishment in the undisturbed grass swards ranged between 0.5 and 9.7% (out of the total number of seeds dispersed) across the dispersal times. The density of alfalfa in fall-seeded plots was about 82% lower than in spring-seeded plots. Soil disturbance reduced the density of alfalfa to < 50% of the initial density. Generally, low plant densities were compensated over time by increased numbers of shoots and reproductive units (racemes and pods) per plant. Herbicide application (2,4-D + dicamba) effectively controlled all emerged alfalfa plants, but in some cases, seedling recruitment was observed in the years following herbicide application. Although mowing did not kill alfalfa plants, mowed plants did not produce mature seeds, and as such, mowing may be useful in restricting the reproductive success and population growth of alfalfa. Overall, it is evident that alfalfa is capable of establishing in competitive environments (such as roadside habitats) and rapidly recovering from moderate disturbances. The results of this study have implications for managing roadside alfalfa and for designing novel trait-confinement protocols for alfalfa.