Simple SummaryThe lesser chestnut weevil (Curcilio sayi) is an emergent pest of chestnuts in the United States. Knowledge of this weevils phenology and the ability to monitor its populations will help us understand how this pest is emerging with expanding chestnut production and provide the means to begin to mitigate its effects on chestnut production. We explored the seasonal emergence of C. sayi in upstate New York through the use of traps and soil microcosms to understand when weevils begin to emerge and when the population peaks. We found that pyramid traps are most effective for monitoring and that populations have one generation that tends to peak late in the season. We also found that generational cohorts may stagger their emergence and delay leaving the soil for more than one year.With the introduction in recent years of high-yield blight-resistant chestnut varieties, the commercial chestnut industry in the United States is expanding. Accompanying this expansion is a resurgence in a primary pest of chestnut: C. sayi, the lesser chestnut weevil. This weevil damages the nut crop and infestations can surge from 0 to close to 100% in as little as two years. Understanding the dynamics of this pest has been challenging. Most work was conducted in the 1900s and only recently has this weevil garnered renewed interest. Recent work on C. sayi phenology has been completed in Missouri but conflicted with anecdotal reports from northern growers. From 2019 to 2020, we used a combination of trapping and microcosm studies to understand both C. sayi phenology and the means of monitoring this pest. C. sayi populations were univoltine and peaked in mid-October. Pyramid traps were the most effective at capturing adult C. sayi. C. sayi larvae, pupae, eclosed adults, and emerging adults were recovered from microcosm experiments. These results suggest that C. sayi emerges later in the northern US with the potential for a single generation to emerge over multiple subsequent years. Understanding C. sayi phenology along with the means of monitoring forms the basis for effective management and control in commercial chestnut orchards.