Eggs are one of the least understood life stages of insects, and are poorly represented in the fossil record. Using microtomography, we studied an enigmatic fossil egg clutch of a presumed entomological affinity from the Oligocene Turtle Cove Member, John Day Formation, from the National Park Service-administered lands of John Day Fossil Beds National Monument, Oregon. A highly organized egg mass comprising a large clutch size of approximately 50 slightly curved ellipsoidal eggs arranged radially in several planes is preserved, enclosed in a disc-shaped layer of cemented and compacted soil particles. Based on the morphology of the overall structure and the eggs, we conclude that the specimen represents a fossilized underground ootheca of the grasshoppers and locusts (Orthoptera: Caelifera), also known as an egg pod. This likely represents the oldest and the first unambiguous fossil evidence of a grasshopper egg pod. We describe Subterroothecichnus radialis igen. et isp. nov. and Curvellipsoentomoolithus laddi oogen. et oosp. nov., representing the egg pod and the eggs, respectively. We advocate for adopting ootaxonomy in studying fossil eggs of entomological affinities, as widely practiced with fossil amniotic eggs. An additional 26 individual and clustered C. laddi collected throughout the A–H subunits of the Turtle Cove Member suggest the stable presence of grasshoppers in the Turtle Cove fauna, and we discuss the paleoecological implications. Oothecae have convergently evolved several times in several insect groups; this ovipositional strategy likely contributed to the fossilization of this lesser-known ontogenetic stage, enriching our understanding of past insect life.