The decline in grasslands and other species-rich early successional habitats on the coastal sandplains of the northeastern United States has spurred management to increase the area of these declining plant communities. We mechanically removed overstory oak and applied seed from a nearby sandplain grassland on the island of Martha’s Vineyard, Massachusetts, to evaluate this technique for creating an open oak community able to support sandplain herbaceous species. We compared vegetation structure and composition before and after clearing in an area of total tree removal (clearcutting), an area where 85% of tree basal area was removed (savanna cutting), and in adjacent coastal oak forest. Plant responses to clearcutting and savanna cutting were similar. Sandplain herbs colonized at high frequencies after seeding and increased herbaceous cover from less than 7% before clearing to 22–38% three growing seasons later. Pennsylvania sedge (Carex pensylvanica) increased in cover approximately 6-fold, accounting for 84–90% of the increased herbaceous cover. Other native ruderals and exotic herbs reached 2 and less than or equal to 1%, cover, respectively, after three years. Species richness across cleared treatments increased from 30 to 79 species. All forest species were retained. Forest shrubs and trees initially declined from their dominant cover but rebounded after three years. Tree clearing plus seeding appeared to be a viable management practice for increasing cover of herbaceous sandplain species while causing minimal increases in exotic herbaceous cover. The long-term persistence of sandplain herbs may require periodic disturbances that limit woody regrowth.