Answer: Hollies can be planted alone and will grow just fine, however you need to plant a male and a female that bloom at the same time to have a fruiting pair if you want to see berries. (Only the female produces berries, but the male supplies the necessary pollen.) There are male and female cultivars with matching names such as Blue Prince and Blue Princess, or China Girl and China Boy to help you get the right set. One male can supply pollen for several female trees. Hollies are best planted in the spring.
There are clumping bamboos and there are running bamboos. The running bamboos can become invasive unless their roots are restricted by strong underground barriers, so planting bamboo should be carefully considered. Your zip code places you in USDA winter hardiness zone 6. Be sure to select a bamboo that is reliably winter hardy in zone 6. You might look at some of the Phyllostachys (for example, Phyllostachys aureosulcata or yellow groove bamboo growing about twenty feet tall and aggressively spreading) or perhaps a Fargesia rufa (clumping, to about 8 feet tall.)
Larger trees planted for shade might include oaks and maples. There are many different cultivars available. Mature size for shade trees often exceeds fifty feet in height and width, so be certain you have sufficient space for such a large tree. In general they will do best with full sun and average soil that is well drained to evenly moist.
Fall is an excellent time to plant deciduous trees.
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