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.
They have lots of sandwiches named after politicians.
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-
These are the massive glasses that hold the 6-pound milkshake. To get a sense of the scale, check out the normal milkshake glasses below.
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.
Hard Bean Coffee & Booksellers is located at 36 Market Space in Annapolis. It is a coffee shop/general store/deli/bookstore combo that’s laid back, but nothing too special. My coffee was fine, but could have been hotter. There is a good amount of space to spread out, though. The location near the waterfront is good too.
Iron Rooster is a restaurant primarily known for its all-day breakfast located at 12 Market
The homemade Oreo pop tart
Space, Annapolis. This place is everything I like to see in a restaurant: the food is delicious, prices are reasonable, the staff is friendly, the location is excellent and it has a nice atmosphere. The offerings are generally comfort food (don’t come here if you’re counting calories). I ordered a homemade oreo pop tart (flavors change daily), which was absolutely massive and delicious. It was somewhat reminiscent of a pop tart but much larger and so much better. I also ordered the “Rooster and a Biscuit,” which is a biscuit sandwich with buttermilk fried chicken,
The “Rooster and Biscuit.”
balsamic honey and raspberry preserves. While a portion of the chicken was less tender than I might have liked, it was otherwise great. Those two items together were way too much food for me, but I’m not in Annapolis every day so I wanted to sample as much as possible. Other choices include Shrimp and Grits, Chicken and Waffles, and much more. The restaurant is located right near the water, with a view of the iconic Ego Alley, and the decor inside is sleek, but comfortable. I highly recommend eating here if you are in Annapolis!
A favorite watering hole of Midshipmen from the Naval Academy, Rams Head Tavern is located at 33 West St, Annapolis, MD. Rams Head Tavern, Annapolis is one of several Rams Head bars and restaurants throughout Maryland. It is easy to see why this place is so popular; the happy hour is awesome and includes a massive selection of beer, including lots of local beers! Their beer selection includes an impressive number of international beers; they even have a World Beer Club for those who drink (over a long period of time and no more than three in one sitting!) all 100 beers on a list. The interior is crowded, but cozy. Overall a great place for a drink.
Purple Thread Cafe is a Vietnamese eatery, cafe and bubble tea spot located at 137 Prince George Street in Downtown Annapolis. This is a small spot offering reasonably-priced Banh Mi sandwiches and other Vietnamese options, such as spring rolls, vermicelli wraps and seafood balls. They also have bubble tea and smoothies with boba. I was looking for coffee so I ordered a French Press Vietnamese coffee with condensed milk. It took a long time to make, but that’s
The Vietnamese French Press coffee was excellent!
because they made it fresh and did it properly. It was absolutely delicious and well worth the wait. The guy working there was chatty and friendly. The place is a bit of a hole in the wall, and not exactly a romantic date spot. It’s certainly not a tourist trap though since it doesn’t attract the visitors looking for crab cakes.
City Dock Coffee is a small coffee shop located in the Market Space near Annapolis’s waterfront (there is an additional location at 71 Maryland Ave, Annapolis). It is a cute little coffee shop, located in Annapolis’s historic core and decorated in a maritime theme. I had a chocolate orange latte which was a bit pricey, but delicious. The staff was friendly. Overall this wasn’t a standout cafe for me, but certainly a nice independent coffee shop to visit if you’re looking for a cafe in Downtown Annapolis.