Chestnut is an economically important tree because of wood and nut production, which is usually found in warm-temperate species, especially Mediterranean region. The fruit of chestnut is a good antioxidant source besides being rich in vitamin C. Anatolian chestnut (Castanea sativa Mill.) is a natural chestnut species in Türkiye. This study aimed to determine the most appropriate grafting time and grafting method for two chestnut cultivars (Marigoule and Erfelek) collected from the Western Black Sea region. Two different varieties (Marigoule and Erfelek) and three different grafting methods (chip budding, tongue, and cleft) were applied in different environments (in the hoop house and open field) for six months (December, January, February, March, April, and July). Analysis of variance was used for the grafting trials which was established and applied in the factorial trial design. Results showed that grafting success in the hoop house was twice as high in the open field, and the tongue was the most successful grafting method in all months except July. However, chip budding was observed as the most successful method in July. The highest grafting success was achieved in February, followed by July. According to the obtained results, Marigoule (C. crenata x C. sativa) cultivars were more successful than Erfelek cultivars. Marigoule cultivar’s success rate was 86% for the tongue method in February at hoop house. In July, 83% grafting success was achieved.