Dry open often sandy plains and small hills, prairies, oak or pine savanna, sand barrens, dry fields.

This is our shaggiest-appearing hawkweed, with hairs toward the base of the plant at least 8–10 mm long and often twice that. As in other species, these are pale when fresh and deep tawny or rusty in color when several years old and dry. The phyllaries are mostly stalked-glandular throughout, while in H. gronovii they are stalked-glandular, if at all, only on the basal two-thirds.