Oak trees can be readily propagated by planting their seeds, but the failure rate can be high due to animals eating the acorns or germination failures due to competition in the soil. According to the University of Minnesota, white oak acorns should be planted in the fall immediately following harvest, while red oak acorns can be planted in the fall or the next spring.
Clear a planting area for each future tree by removing any plants, old stumps, debris and weeds in a half-acre site. Filtered overhead shade from the canopies of large nearby trees is acceptable but keep a half-acre footprint for each oak tree.
Harvest a minimum of eight mature acorns for every eventual tree you would like at the site. This over-planting will compensate for germination failure and loss of acorns due to animals foraging for food. Lift off the acorn caps if they have not already fallen off.
Till 6 inches of cleared soil and plant your acorns 1 to 2 inches deep in the soil. Use a minimum of eight acorns for every half acre of soil, each several feet apart. The acorns can be oriented any direction in the soil. Tamp down the soil lightly to ensure good contact and fix the acorn in position.
Water deeply to drench the soil immediately surrounding the acorn. Mark the planting spot with stakes, flags or tags.
Monitor the planting area once a month or so until the seedling is at least 3 years old. Pull all competitive weeds and plants that crop up in the planting area. Maintain evenly moist soil at all times.
Thin or transplant excess seedlings, if needed, in their third year into pots or another ground planting location.