Hi Kathleen, your May trip is coming up and I'm sure you are getting really excited for some magic!
While it is never easy to guess how long a wait will be at any given time of day or year, I can say that May will have less crowds than the spring break time frame. Unless you go around Memorial Day, this is a great time to visit due to the moderate to low crowd levels. I would suggest getting the official mobile app, My Disney Experience (available for iPhone and Android). This app can give you the most up to the minute wait times as well as many other fun features to help you navigate your vacation better.
Along Main Street, USA, you will find mostly retail shops ranging from the Emporium that sells all kinds of fun souvenirs and Disney Parks specific merchandise to Uptown Jewelers and Crystal Arts that sell more expensive wares such as collectibles, jewelry and glassblown pieces. In addition to the stores, there is the Harmony Barber Shop for haircuts and delicious food service options like Main Street Confectionery, Casey's Corner, and Tony's Town Square to name a few. Lastly, near the front entrance to Main Street, USA near the train station is City Hall for guest services, the Firehouse (recruitment center for
Sorcerers of Magic Kingdom), and
Town Square Theater, where you can meet Mickey Mouse, himself. Lastly, you can catch some fantastic entertainment from the
Citizens of the Main Street, USA, as well as, the famous
Dapper Dans.
Have a wonderful trip. It will be here before you can say "supercalifragilisticexpialidocious!"
~Allison L