Chick & Ruths Delly (yes, they spell it “delly” instead of the typical “deli,” is an Annapolis institution that has been in business since 1965 located at 165 Main Street. It is a wonderfully quirky, classic place that has a fantastic crab cake sandwich that is the best I have ever had.
It’s always 5 O’Clock at Chick & Ruths Delly, where wine and beer costs $2.99 all day, every day. The decor is classic 1960s and the walls are absolutely covered with signed photos of famous people who have eaten there. Another quirk of the place is that the restaurant recites the Pledge of Allegiance each morning. They also have a large number of sandwiches named after local and state politicians. One of their most iconic offerings is the absolutely monstrous 6-
pound milkshake (I did not order this, but the staff told me that occasionally people finish it alone). The place certainly appeals to tourists as well as locals, and does get packed at peak hours. But the staff is friendly, the prices are reasonable, and there is probably no better place to eat if you want to experience a uniquely Annapolis phenomenon.