Plant Chester Blackberry in well-draining soil enriched with organic matter, ensuring it receives full sunlight for optimal fruit production. Water consistently, especially during dry spells, to maintain soil moisture and promote healthy growth. Prune annually in late winter to remove old canes and encourage new growth, which enhances fruit yield. Support the plant with a trellis or similar structure to keep canes upright and facilitate air circulation. Fertilize in early spring with a balanced fertilizer to provide essential nutrients.