If you're going to be stuck on the east coast for a month, you should find a chance to get something fresh from the ocean, especially if you're a Midwesterner like myself. Annapolis is rife with fantastic restaurants, and I managed to get into Chick and Ruth's Delly before the dinner rush hit.
It couldn't be a world class restaurant without insane food challenges. Chick and Ruth's has four food challenges you can try.
Their extensive menu is available all day, and they named most of their sandwiches after former and current Maryland state legislators and judges. After all, the restaurant is located just down the street from the Maryland State House, and is a favorite lunch spot for the politicians.
But I'll say as someone who isn't huge on seafood, these crab cakes were fantastic. I imagine this is what it's like all up and down the east coast.
Chick and Ruth's Delly is open Monday through Thursday 6:30am-11:30pm and Friday and Saturday from 6:30am to 12:30pm. Get there before the rush, otherwise you'll find yourself waiting for upwards of an hour.