The squash bug, Anasa tristis (DeGeer) (Hemiptera: Coreidae), is an indigenous pest of squash and other cucurbits. Pesticides can control squash bug populations although many small-scale growers in the Southeast seek alternative methods of management. Cultural control methods, including varying the planting date and farmscaping, are not well understood under southeastern conditions. The goal of farmscaping is to increase natural ecosystem functions to aid in the control of pest populations. In the summers of 2014 and 2015, field plots of squash, separated by a minimum of 150 m were organized in a split-split plot design, with floral resources at the whole-plot level and varied planting date at the subplot level. Data were collected on squash bug abundance and fruit yield (kg), and abundance of potential natural enemies of A. tristis. Plots with added floral resources had fewer squash bug adults than plots without added floral resources in four of eight possible year × site × planting date combinations. Furthermore, the site in 2014 which had a reduction in squash bug adult abundance also had an increase in the abundance of potential enemies, including spiders, ground beetles, and predaceous Hemiptera. There were additional instances when potential natural enemy abundance was greater in resource-enhanced plots, but they were not associated with sites that had a reduction in yield loss or squash bug abundance. The use of floral resources to attract natural enemies and beneficial insects merits further investigation.