Check out the Southern Maryland Astronomical Society:
http://www.smas.us/html/Programs.html
They have fairly regular observing sessions at the Nanjemoy Creek Environmental Center in western CC. However, their members come from all areas of So MD and they often have "star parties" at various schools.
Contact them - get to know some of their members. You will find a wealth of knowledge and lot of experienced observers that will give you good advice on types and kinds of scopes and accessories. In astronomy, like all hobbies, it helps to have access to knowledgeable experienced participants for advice on what and what not to buy.