There are considerable differences in chestnut yield and quality across different chestnut-producing regions in China, indicating that environmental factors affect these properties of chestnuts. Furthermore, nut yield and quality differ depending on canopy position. Therefore, this study investigated the relationship between the canopy microclimate, nut yield, and quality. We determined microclimate factors from blossoming to ripening at different positions in the canopy. Nut yield and quality and the number of different branch types were measured at various canopy positions. The light intensity and temperature of the different canopy layers exhibited funnel-form distributions ranging from 0 to 3600 μmol·m2·s−1 and from 32 to 37 °C, respectively. Canopy humidity showed an inverted funnel-shaped distribution ranging from 26% to 40%. Nut yield and quality in the top and outer canopies were higher than in the bottom and inner canopies. Branches in the top-middle and peripheral parts of the canopy also produced higher yields, especially strong branches that bore more nuts. Nut yield and quality had positive correlations with light intensity (r = 0.735) and temperature (r = 0.709), whereas they were inversely associated with humidity (r = −0.584). The nut yield was more than 200 gm−3 when the light intensity was above 1500 μmol·m2·s−1, the temperature was above 34.4 °C, and the humidity was below 27.5%.