Now that I’ve discovered Chick & Ruth’s Delly, it’s become my go-to place whenever we find ourselves in Annapolis. I found the place thanks to some great reviews on Trip Advisor. It’s honestly one of those restaurants that is just full of character, so its worth a visit if you’re up for adventure.
Chick & Ruth’s Delly is located right on Main Street in downtown Annapolis. It’s 3 blocks from the Harbor and easy walking distance from the US Naval Academy. Parking is a bit tricky in Annapolis, but there is a parking garage about 1 block away called the Noah Hillman Garage.
The restaurant is not that impressive to look at from the inside or the outside, but it’s part of the character that I was talking about. The building has a green awning beneath a vintage bright orange sign. The front window is covered with pages from the Menu and you’ll generally find customers lining the sidewalk. In my experience, the best thing to do is just march right inside and flag down the nearest waiter/waitress and ask to be added to the list for a table. The restaurant is small and usually crowded so the smaller the party, the better your chance of getting a table quick.
After a short wait, you will be escorted to a booth. The menu for the restaurant is the most haphazard menu you’ve ever seen (see above). It’s okay though, you probably have plenty of time to figure out what you want to order because the waitstaff always seem busy. But they”ve also always been incredibly nice. It’s a “delly” (I have no idea why they spell it that way), so I generally order a sandwich with pastrami or corned beef or the one above which is a combination of both. It doesn’t take too long for the food to arrive and while you wait, they provide a whole bin of homemade cucumber pickles that are delicious. The restaurant charges you a pretty big fee to split a sandwich, so just order yourself a whole one and take half home if it’s too much (it probably will be). The sandwiches do not come with french fries or any sides so those are ordered separately and can probably be skipped because they aren’t anything special. Instead, I recommend saving some room because the restaurant is also known for having something like 30 different flavors of fresh pie which they sell for $1.99 a slide.
If you find yourself in Annapolis, don’t be scared off by the shabby, crowded appearance. It’s really a fun experience if you can handle it!