The lesser (or small) chestnut weevil, Curculio sayi (Gyllenhal), is the key economic pest of chestnut in the central and eastern regions of the United States. Previous research identified the major components of the volatile profile emanating from several chestnut plant tissue types. The goal of this project was to evaluate for the first time the physiological (via electroantennogram) and behavioral (via Y-tube olfactometer) responsiveness of C. sayi to blends of selected key chestnut volatile organic compounds (VOCs) across weevil sex and seasonal period of adult activity. The VOC treatment mixtures that generated the highest (and mostly significant) mean electroantennogram (EAG) responses for both sexes and periods of adult activity were the 2-compound mixture treatments, specifically the treatments of 2-heptanone ethyl butyrate, 2 heptanone (E)-2-hexenal, and (E)-2-hexenal ethyl butyrate. All 3- and 4-compound mixtures generated significantly lower mean EAG responses than most of the 2-compound mixture treatments. Results of the behavioral study did not reflect the results from the EAG study. Both male and female weevils, regardless of when they were collected during the season, did not exhibit a significantly greater preference towards any of the VOC mixture treatments compared with a control. As such, further studies must be conducted on additional chestnut VOCs in order to identify the optimal blend (and ratios of), as well as dosage, that will elicit a positive behavioral response before such VOCs can be utilized in a C. sayi monitoring and/or management practice.