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1. The Maryland State House is what picture?
1. Bancroft Hall | 2. Banneker-Douglass Museum | 3. Maryland State House | 4. St. John's College (Annapolis)
2. What river is Annapolis situated on the mouth of?
3. What major bay is Annapolis on?
4. What was the old name of Annapolis when first settled?
Providence > Town at Proctor's > Anne Arundel's Towne > Annapolis
5. Which U.S. Military Branch has their academy in Annapolis?
The United States Naval Academy was first made ere, but was temporarily at Newport, Rhode Island during the Civil War.
6. Which peoples founded Annapolis?
7. The largest storm surge in Annapolis came from which Hurricane?
Hurricane Isabel beat Hurricane Hazel back in 2003.
8. What was the 2007 Annapolis Conference about?
9. What is Annapolis the smallest of, in terms of capital cities?
10. Someone from Annapolis is called a(n) what?
Question like 1, 6 and 10 are best avoided, as they can are uninteresting or just guessing games.
You said you want to do alot of Maryland cities, well having to see these questions repeated amongst all of them isn't very interesting.
Cities have so much to talk about, I'm sure you can find better questions then those 3.
Maybe make it 4 pictures and ask which of these is x building