North American grasslands make up less than 75% of their historic pre-European settlement area, and they continue to be converted to woodlands by woody plant encroachment. Conversion of grassland to woodland alters nutrient cycling, water use, and light penetration, which drives herbaceous plant community dynamics. Because studies examining this relationship among Juniperus species are limited largely to individual trees, we designed a study to examine the relationship between stand-level canopy cover of eastern redcedar (Juniperus virginiana L.) and the herbaceous plant community. We documented herbaceous plant species composition, abundance, and biomass within a North American tallgrass prairie invaded by eastern redcedar in which canopy cover of eastern redcedar ranged from 0% to 80%. Herbaceous species richness declined as a function of increased canopy cover of eastern redcedar and subsequent loss of open space, but this decrease in species richness closely followed a species–area model. Moreover, composition of C₃ and C₄ grasses and forbs did not change with increasing canopy cover. Herbaceous biomass, which declined with increasing canopy cover, varied most within those plots with intermediate canopy cover. While we found that species richness and biomass declined as canopy cover increased, the decline followed a species–area relationship and was without abrupt change typical of ecological thresholds. We recommend additional research with removal of eastern redcedar trees over a range of canopy cover to assess restoration potential along the encroachment gradient.