Although prenatal exposure to high ambient temperatures were reported to be associated with preterm birth, limited research assessed the impact of weather-related extreme heat events (EHE) on birthweight, particularly by trimester. We, therefore, investigated the impact of prenatal EHE on birthweight among term babies (tLBW) by trimester and birthweight percentile. We conducted a population-based case–control study on singleton live births at 38–42 gestational weeks in New York State (NYS) by linking weather data with NYS birth certificates. A total of 22,615 cases were identified as birthweight <2500 gram, and a random sample of 139,168 normal birthweight controls was included. EHE was defined as three consecutive days with the maximum temperatures of ≥32.2 °C/90 °F (EHE90) and two consecutive days of temperatures ≥97th percentile (EHE97) based on the distribution of the maximum temperature for the season and region. We estimated odds ratios (ORs) and 95% confidence intervals (95% CI) with multivariable unconditional logistic regression, controlling for confounders. Overall exposure to EHE97 for 2 d was associated with tLBW (OR 1.05; 95% CI 1.02, 1.09); however, the strongest associations were only observed in the first trimester for both heat indicators, especially when exposure was ≥3 d (ORs ranged: 1.06–1.13). EHE in the first trimester was associated with significant reduction in mean birthweight from 26.78 gram (EHE90) to 36.25 gram (EHE97), which mainly affected the 40th and 60th birthweight percentiles. Findings revealed associations between multiple heat indicators and tLBW, where the impact was consistently strongest in the first trimester.