Chestnuts are almost easier to plant than they are to crack open and eat. According to the American Chestnut Foundation, since a blight wiped out a large portion of North America's native chestnuts in the first half of the 20th century, its not as easy as it once was to find wild chestnuts to plant. Nowadays, the chestnut you plant is likely to come from the grocery store or an online source. Although there's no foraging involved in obtaining the seed, planting store-bought chestnuts is no different or more difficult than planting wild ones.
Contact your local county extension office and have them perform a test of your soil (for a nominal fee). Chestnut trees need mildly acidic, well-drained sandy loam soil to thrive. The resulting test will reveal your soil's suitability for growing chestnuts and dictate any amendments that must be added before you plant. For the best result, incorporate any amendments to the soil six months to one year before planting your chestnut seeds.
Prepare the chestnut's hole in early spring for fall planting. Dig a hole that is 2 feet in diameter and 2 feet deep. Set aside half of the excavated soil and mix it with an equal amount of peat moss. Refill the hole with the amended soil.
Plant two chestnut seeds, side by side in October. Place each seed on its side and press it into the soil with its pointed end facing the opposite direction of its neighbor's. Cover each of the seeds with 1 inch of peat moss.
Water the planting area so that it is moist to the depth of the chestnut seeds. Continue to keep the planting area's soil moist for the first three years of your chestnut's growth.
Place a 5-foot-tall wire tree shelter (with 2-by-4 inch grid and a 2 1/2-foot diameter) around the planting area, buried 3 inches deep into the soil. Hammer a 4-foot rebar stake 1 foot into the earth next to the cage and secure the cage by tying it to the stake.
Cover the shelter with mesh netting. Leave it in place until May.
Remove the tree shelter as the chestnut tree grows.