Shenandoah Shakespeare is such a fun theater to see a Shakespeare play (and sometimes non-Shakespeare plays, especially during the holiday season). It is one of the additions to Staunton that really helped to revitalize the downtown area. It's a beautiful, small theater modeled after The Globe.
1) If you are tight on cash, check out their "Pay As You Will" nights, typically on Wed or Thursdays...you get in for free and then pay what you want on the way out, depending on how well you liked the show!
2) There is a great coffee house around the corner (aptly named Coffee on the Corner") where you can get a nice hot (or cold!) drink and discuss the show after visiting the theater!