It's not hard to do; you have to start seedlings in a raised bed and transplant them later to their permanent planting plot.
1) First, store the acorns in a sealed plastic bag in the refrigerator until you are ready to plant them, preferably this fall.
2) In a semi-shaded wooded area, prepare a raised soil bed of rich humus-filled woods dirt; size proportionate to the number of acorns you are planting. Gently push each individual acorn, with the cup down, into the dirt about 2 inches deep, about 5 inches apart. Cover the acorns loosely with dirt. If you plant 300 acorns, less than 50 will germinate and sprout, about 18 months later. Squirrels, moles/voles and mice will eat most of them; some will rot, deer will dig them up; but you should end up with about 50 nice little sprouts for later transplanting if you start them this fall. You can cover your bed with chicken wire to prevent some predation, but be sure to remove it before the acorns sprout.
Most acorns have to stratify in the ground for about 18 months before they sprout; however a few (about 20 percent) will sprout the following spring. If you plant them this fall, most of them will not come up until the second spring, not the following spring. This is variable information, but typically what occurs under natural conditions here in the southern appalachian mountains. I'm sure local conditions across the US will vary.
After the seedlings come up, leave them in the bed for about 4-5 years before digging them up for transplanting.
Have fun and enjoy your chestnut oaks. If good growing conditions are met, they will reach about 8-10 feet high and start bearing acorns in about 10-12 years. They make excellent wildlife food as well as a really great shade tree.
You can also start chinese chestnuts with good success using this method.
