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Downtown Annapolis Restaurants and Bars: The Perfect Game Day Weekend

Can’t decide where to eat and drink during a weekend in Annapolis? Our review of the best Naptown has to offer.

News: John McCain U.S. Naval Academy USA TODAY NETWORK

Annapolis is often referred to as “America’s Sailing Capital,” but many visitors may not be aware of the growing food and bar scene that has thrived in downtown the last few years. While the self-proclaimed sailing title is worthy of debate, no one can turn a blind eye to the incredible food dishes that DTA (Downtown Annapolis for the tourist type) provides. While Flip in Wedding Crashers summed it up best – “crab cakes and football – that’s what Maryland does,” Downtown Annapolis food is more than a one-trick-pony.

Although some Annapolis restaurants serve the best crab dishes in America, DTA provides a plethora of restaurant and bar options that visitors can enjoy no matter what your taste buds prefer. Our goal is to provide you with some of the best game day weekend options as it pertains to the breakfast, lunch, and dinner in Maryland’s state capital.

Of note, while these establishments may be listed under one specific category in this blog, they often serve breakfast, lunch, and dinner. The tweets/pictures represent my trip to Annapolis for the Navy vs. Houston 2018 football game and do not incorporate even close to ALL of the options Annapolis has to offer. In fact, if you have a favorite that I didn’t include, please let us know in the comment section below. The goal of this piece is to provide visitors with some direction regarding the food and drink choices in Annapolis from one college football fan to another.


No weekend trip to Annapolis is complete without hitting up a couple of the well-known breakfast/brunch spots. Since my most recent visit lasted three days, I was able to visit three of my personal favorites.

Iron Rooster – 12 Market Place, Annapolis, MD 21401

Iron Rooster serves breakfast all day and is a must-visit no matter what time of the day you plan to enjoy Annapolis. The restaurant is known for its breakfast dishes and, in particular, its homemade “RoosTarts.” Beyond the incredible food and awesome service, Iron Rooster thrives in two other key areas that SB Nation readers should love. First, they have an interactive social media presence that leaves your mouth watering with pictures promoting their best menu items, and second, they are extremely supportive of Naval Academy athletics. You really haven’t tried Annapolis food if you don’t visit Iron Rooster, nor would any review of Annapolis’ restaurant scene be legit without starting it off talking about an emerging Maryland staple.

Clockwise from top right: Iron Crush, Mimosa, BACON, Pumpkin RoosTart

Miss Shirley’s Café – 1 Park Pl, Annapolis, MD 21401

Some people try to pretend that you can’t like both Iron Rooster and Miss Shirley’s – They tell you that you have to pick a side. It’s like the great Pat’s or Geno’s battle in Philly but instead involves mimosas and hash browns. While these folks may tell you that you have to pick one, I tell you they couldn’t be more wrong as both places are some of the best brunch options in all of Maryland. Miss Shirley’s serves an assortment of tasty morning cocktails (Spicy Shirley with crab meat or a Chesapeake BBQ Bloody Mary), unique menu items such as its “Coconut Cream Stuffed French Toast” and “Funky Monkey Bread”, and breakfast staples such as three-egg omelets and, of course, bacon.

Boatyard Bar and Grill – 400 4th St, Annapolis, MD 21403

On the other side of the Spa Creek (or 6th Street) Bridge is the small neighborhood of Eastport. Visit Annapolis labels Eastport as “A Different Side of Annapolis”, noting that the pace is a little slower than the pedestrian and vehicular traffic that often accompanies DTA. Boatyard Bar and Grill takes the Eastport relaxation one step further by providing a laid back nautical atmosphere inside the restaurant and merges that with delicious and fresh food options to create a one-of-a-kind Annapolis experience. Known for its crab cakes and local seafood, Boatyard brings many of the locals to its tables with some of the best meals on either side of the creek. While the restaurant would also be a great lunch or dinner selection, it has a penchant for drawing the weekend brunch crowd with its early bird special - $2 mimosas and bloody marys before 10 am (weekends only).

Background: Shrimp and Grits. Foreground: The Annapolitan Omelet (with lumped crab meat).


Rams Head Tavern – 33 West St, Annapolis, MD 21401

For those that may not follow Navy football closely, there is about a 95% chance that the game will start at 3:30 PM. By the time the game is over, you will be thirsty, hungry, and likely wanting to find a place to watch the prime time games; if that’s the case, Rams Head is definitely your spot. Rams Head features over 150 beers and a “World Beer Club” that tallies each consumed beer in your quest to tackle them all. While that feat is unlikely to occur in a single weekend visit, it is a rite of passage for many USNA alumni. Rams Head is more than just good beer, however, as the restaurant serves up some top-notch pub fare featuring fresh seafood dishes and mouth-watering burgers. Come for the beer and food, but stay for the TVs in the bar area that will certainly be showing you the best college football has to offer (they also serve brunch and show all the NFL games if you want to save this trip for Sunday afternoon instead).

Crabby Tots and the Beer Sampler provided by Fordham and Dominion Brewery
Background: Blackened Tuna with Shrimp. Foreground: Fondue Burger

The Big Cheese – 47 Randall St, Annapolis, MD 21401

After Commissioning week my Second Class (Junior) year, I packed up my Buick and started to plan my trip home to Virginia Beach for a few weeks before kicking off my summer training. Once the car was packed and ready to go, I knew I had to get to The Big Cheese and order four of my favorite sandwiches of all time- the Annapolitan, the Annapolitan, the Annapolitan, and the Annapolitan. You see, I love the Annapolitan sandwich so much that I wanted to have them back home with me to start the summer off right. By purchasing four of these delicacies my plan was to put them in my freezer and eat one a week for the first month of summer. I failed. I couldn’t wait a week between sandwiches and devoured all of the sandwiches within three days. The delicious combination of granny smith apples and brie melted over turkey and honey mustard all within two slices of multi-grain bread was too good for a weekly wait. While the deli doesn’t feature any indoor seating, the sandwiches are perfect for the gameday tailgate. They also sell beer and champagne, essentially serving as the one-stop shop for all of your visitor tailgating needs.

Fox’s Den – 179 B Main St, Annapolis, MD 21401

Stepping down into the basement level of 179 Main Street and walking into a dimly lit bar makes you feel as if you found a hidden gem, but the Fox’s Den is a well-known restaurant and bar that serves some of the best pizza and craft beer in DTA. The rustic appearance matched with the aroma of the wood fired pizzas make this a must visit destination when visiting Annapolis. If pizza isn’t your thing, come for the drinks and split the duck fat fries with your friends– easily the best fries in the area.

The Fig & Pig Pizza featuring fig preserves, country ham, brie, torn mint, hot honey

Vida Taco Bar – 200 Main St, Annapolis, MD 21401

I must admit that I have only made it to Vida Taco Bar one time as it is a newer establishment that hit Main Street within the last few years. We were looking for a small meal that was going to hold us over until dinner and we knew we wanted some margaritas. Luckily for us, Vida Taco Bar was the perfect solution. The restaurant features daily specials and a number of taco options to include chorizo, mahi-mahi, carne asada, lamb barbacoa (yummy!), and plenty more. These tacos can be served with flour or corn tortillas or even an option of bibb lettuce. While the tacos are certainly appetizing and worth the visit, the freshly made margaritas will keep you in your seats for a fun happy hour visit.

The happy hour house margarita


Pusser’s Caribbean Grille – 80 Compromise St, Annapolis, MD 21401

If you are looking to have drinks with a beautiful view of the Annapolis Harbor, Pusser’s certainly sits atop that list. The restaurant features three bars, one of which is outside on the back deck which parallels the Annapolis City Dock. Pusser’s is home to the original Painkiller and just one sip of the tropical rum-based drink will have you feeling like you are sitting along a Caribbean beach with sand nestled between your toes. While the outside temperature may be in the 40s (depending on the time of your visit), the views and Caribbean setting of Pusser’s will allow you to escape into an island of serenity. (The Painkiller will help to speed up the process, trust me). Pusser’s also has an incredible seafood menu and serves brunch on the weekends.

Annapolis Harbor view from the outside bar at Pusser’s

Dry 85 – 193 B Main St, Annapolis, MD 21401

This is easily my favorite bar in Annapolis and fortunately for me, it didn’t exist when I as a Midshipmen. I imagine if I had the option to visit Dry 85 on a weekly basis I would have even less money in my 401k. The restaurant and bar focuses on its bourbon selection and balances that with a Prohibition style atmosphere to create a century-old experience that is unmatched by any other bar in DTA. While the whiskey flights are essentially required tastings, the cocktails and food menu options make Dry 85 an Annapolis grand slam no matter the occasion. They also feature two TVs that were playing the two best sporting events of the night on my last visit – game seven of the 2018 NLCS and Purdue’s upset of Ohio State.

Left to right: The Lavender Fields of Kentucky, Fire & Smoke

As I compiled this list together, I know I failed to include some of your Annapolis favorites. Shoot, to be honest, I didn’t get to include every restaurant and bar I enjoy visiting when we are in the area, but there’s only so much you can squeeze into a three day weekend. I encourage everyone to add their restaurant and bar of choice in the comment section below to help future Annapolis visitors out when they are trying to narrow down all of the incredible options that DTA has to offer on a Saturday in the fall.