Alien species are often first introduced to urban areas, so it is unsurprising that towns and cities are often hotspots for invasions. However, while large cities are usually the first sites of introduction, small towns are more numerous and have a greater chance of launching invasions into natural areas as they have proportionally larger interfaces with their surroundings. In this paper we develop a set of scenarios as hypotheses to explore the role of small towns in facilitating within-country dispersal of alien plants. In particular, we developed ten scenarios for how introductions to small towns, agricultural and natural areas can lead to landscape-scale invasions. We tested a part of these scenarios using a case study of a highly invaded region in South Africa (the Berg River catchment in the Western Cape). We specifically investigated the main plant invasion routes between 12 small towns and their surrounding agricultural and natural areas. This was accomplished by conducting urban-specific alien plant surveys in towns, then comparing these results to regional databases of naturalized and/or invasive plants. Many of the alien plants found in urban areas were listed as invasive or naturalized in the catchment (over 30% of the total alien species pool). Despite marked environmental gradients across the study area, we found no relationships between the alien plant species richness in towns and climatic variables or with levels of anthropogenic disturbances. All towns hosted large numbers of invasive plant species and nearly half of the alien species found in towns were naturalized or invasive in surrounding areas. The likelihood of alien plants being naturalized or invasive outside urban areas increased in proportion to their local abundance in towns and if they were tall and woody. Ornamental horticulture was the main reason for introduction of these alien species (69%). Small towns can and do harbour significant populations of plant taxa that are able to spread to surrounding natural areas to launch invasions. Comparing lists of species from urban alien plant surveys with those from naturalisation records for the region is a useful protocol for identifying species which may be moving along the introduction–naturalization–invasion continuum.