Thirty-one species of Calymmaria are described or redescribed and illustrated. Twenty-two species are described as new: Calymmaria alleni, C. bifurcata, C. carmel, C. farallon, C. gertschi, C. humboldt, C. iviei, C. minuta, C. monterey, C. orick, C. rosario, C. rothi, C. scotia, C. sequoia, C. sierra, C. similaria, C. siskiyou, C. sueni, C. tecate, C. tubera, C. virginica and C. yolandae. A key to all thirty-one species is provided. Calymmaria quadrata (Exline 1938) is synonymized with C. emertoni (Simon 1897), and C. cavicola (Banks 1896) and C. montavencis (Bishop & Crosby 1926) are synonymized with C. persica (Hentz 1847). Tegenaria modesta Banks 1898 and the replacement name T. modestella Roewer 1944 are treated as nomina dubia. The male palpus of C. lora (Chamberlin & Ivie 1942) and C. emertoni (Simon) are illustrated for the first time along with the internal structure of the female epigynum of C. californica (Banks 1896) and C. shastae (Chamberlin & Ivie 1937). Information is provided on habitat and web structure in the genus. A cladogram of the species of Calymmaria is presented based on a cladistic analysis of characters. The presence of a dorsal patellar fracture line is hypothesized to be an apomorphic character state that relates Calymmaria to five other agelenoid genera: Willisus, Blabomma, Yorima, Cybaeota, and Cybaeina.