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Annapolis Restaurants You Should Be Dining At This Week

Enjoy amazing food at our favorite spots around the town.

Annapolis once served as the capital of the United States during the revolutionary war. Today, it is a town full of historic buildings that will take you back to that eventful period.

chef designing dish at annapolis maryland restaurant

In addition to having one of the country’s best waterfronts, Annapolis is also known for its thriving fishing culture and is a lovely place to explore, especially by boat.

Feel free to sail, look out onto the water, visit the historical museums or walk around taking in the city’s beauty.

Best Restaurants in Annapolis, Maryland

  1. Vin 909 Winecafe
  2. Boatyard Bar & Grill
  3. Carrol’s Creek Cafe
  4. Galway Bay Irish Restaurant and Pub
  5. Preserve
  6. Osteria 177
  7. O’Leary’s Seafood Restaurant
  8. Chick & Ruth’s Delly
  9. Lewnes’ Steakhouse
  10. Iron Rooster- Annapolis
  11. Davis Pub
  12. Jalapenos
  13. Café Normandie
  14. Reynolds Tavern and 1747 Pub
  15. Sailor Oyster Bar
  16. Dry 85
  17. Level a small plates lounge

Foodies will also be happy to know that several restaurants in town have fascinating themes, and they can explore them while in the city. Below I will be reviewing some of the best options from the Annapolis food scene.


Vin 909 Winecafe

909 Bay Ridge Ave, Annapolis, MD 21403
Phone: 410-990-1846
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Vin 909 is a wine bar and restaurant that serves fantastic farm-to-table New American cuisine. You can’t go wrong with any of their well-prepared dishes, such as the clams and butternut squash.

You could also try one of their extremely popular brick oven pizzas – this is the option I went for during my solo dining experience. The food and wine selections are excellent while staying surprisingly reasonable in price.

The decor is tasteful on the inside, and the outside is even more stunning. To make it even better, outside the entrance to the restaurant is a uniquely styled area with fascinating floral arrangements flanked by lots of shrubberies.

The Flora is well-maintained and almost always attracts crowds to admire the display for a while before going inside.


Boatyard Bar & Grill

400 Fourth St, Annapolis, MD 21403
Phone: 410-216-6206
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Boatyard Bar and Grill is a nautical-themed seafood restaurant with excellent service and incredible crab cakes! The place is a little on the pricey side, but you will get your money’s worth.

My crab cakes were so flavorful, and the mashed potatoes on the side paired perfectly with them.

However, diners who visit in the evenings may be disappointed with the wait times because the restaurant usually fills up. Also, they are only open from Friday to Sunday, which is a bummer.


Carrol’s Creek Cafe

410 Severn Ave, Annapolis, MD 21403
Phone: 410-263-8102
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Sitting right by the water off Severn Avenue is Carrol’s Creek Cafe: an elegant water waterfront seafood restaurant that overlooks Spa Creek.

Be sure to get seating right by the railing to enjoy calming views of the harbor as you while your afternoon away.

Groups dining with young children will be happy to know that the restaurant has high chairs available and a kids’ menu.

Our waiter told me they have a happy hour every Sunday to Friday (5 PM to close), which is very popular with locals because of the discounted appetizers.

My friend had been here before, and he praised the scallops when I asked him what to order. I must say, I was not disappointed! They also have an extensive wine and beer list.


Galway Bay Irish Restaurant and Pub

63 Maryland Ave, Annapolis, MD 21401
Phone: 410-263-8333
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Fancy a trip to Ireland? Well, I can’t exactly help you with that, but the next closest thing that I would recommend is a trip to Galway Bay on Maryland Avenue.

If you want to deepen the Irish experience, mark Saint Patrick’s Day on your calendar and visit on that day. The pub gets very festive, and the energy is infectious.

Fine whiskey is something the Irish are synonymous with, and Galway Bay has an extensive collection of authentic Irish whiskeys. Let me rephrase that!

They have massive in-wall glass displays with rows and rows of Irish whiskeys! It’s a little dizzying, and if you are not a whiskey connoisseur, I recommend you have a server help you make a selection.

It’s pretty evident by now that I was there for the drinks, but I did have their lamb cheesesteak as well, which was the perfect kind of savory.


Preserve

164 Main St, Annapolis, MD 21401
Phone: 443-598-6920
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Upon seeing the shelves full of pickled vegetables on one of the restaurant’s walls, you might chuckle to yourself thinking about how Preserve’s name is a little too on the nose.

Well, you wouldn’t be entirely wrong because Preserve is a casual American restaurant with a particular emphasis on maintaining the use of local produce and products as well as sustainable practices.

You will notice this and different elements around the restaurant, like the reclaimed leather bar stools.

The founders, Michelle and Jeremy, worked different restaurant jobs for over five years, then later honed their culinary skills at the Culinary Institute of America before opening the joint.

The proverbial 10,000 hours of practice is seen clearly in their food. We had the pupusas, mushroom cheese “steak,” and the duck two ways, and the custom selection of pickled vegetables brought some much-needed zing to the whole meal. We had a great time there!


Osteria 177

177 Main St, Annapolis, MD 21401
Phone: 410-267-7700
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Osteria is the Italian word for “host.”, and true to the restaurant’s name, you immediately encounter friendly service as you walk through the Osteria’s doors.

With time, I found that my best culinary experiences came when I was able to mix different flavors with my food order.

Knowing Osteria’s reputation, I had this very goal in mind, so I ordered the blueberry pie alongside my seared duck breast, and I was very impressed.

Our server was very attentive, and we later found out she was a certified sommelier, so we took advantage of this and had a mini wine tasting session as she explained the different notes and flavors in each selection.


O’Leary’s Seafood Restaurant

310 Third St, Annapolis, MD 21403
Phone: 410-263-0884
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O’Leary’s Seafood Restaurant is on 310 3rd Street, right in the heart of the affectionately named the MRE (Maritime Republic of Eastport). The restaurant’s bright azure exterior is hard to miss, so finding it should not be a problem.

We asked about the staples, and after consulting with our server, we settled on the rockfish, which was adequately breaded and oh so crispy!

My friend and I also wanted to try their craft cocktails. He had a gimlet while I had the carrot juice and mushroom option, which the restaurant called the “Fear & Loathing.”

I took the cocktail suggestion from the mixologist operating the bar. I don’t know how the name for the drink came about. All I know is that I enjoyed it.


Chick & Ruth’s Delly

165 Main St, Annapolis, MD 21401
Phone: 410-269-6737
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Chick & Ruth’s Delly is quite the trip, literally! The wall decorations and chrome trim bar stools are very 60s-esque and relics of an old establishment still chugging along 50 years later.

It is lovely to see the history and changes of the moments captured in the framed pictures on the walls.

I made two stops here in the same week. The first time I was in a bit of a rush and could only grab their blueberry muffins on the way to my morning meeting.

The muffins were fresh from the oven, very moist, and such a delight to bite. It was the perfect way to start the day.

Later in the week, I had more time, so I decided to sit in and enjoy the ambiance as I had my Western breakfast omelet with cheese. My eggs were to the precise consistency I specified in my order and stimulated the senses when paired with my coffee.


Lewnes’ Steakhouse

401 Fourth St, Annapolis, MD 21403
Phone: 410-263-1617
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Lewnes’ steakhouse has been serving food out of its current location since 1921 and is a family-owned business whose management has passed down four generations.

Brothers Sam and Mack Lewnes currently run the joint and ensure the continuity of this historic restaurant.

I had a medium-rare tomahawk steak, seafood bisque, and some champagne. My group was in a celebratory mood, so we decided to splurge a little. Seasoning for steaks can be a hit-or-miss affair, but our chef got it right for that day.

The staff were so gracious and even decided to surprise us with brownie milkshakes after they heard we were there to celebrate a friend’s achievement. Such “above and beyond” service is what keeps customers coming back.


Iron Rooster – Annapolis

12 Market Space, Annapolis, MD 21401
Phone: 410-990-1600
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There is some pleasure to be derived from doing something when you’re not supposed to be doing it. Perhaps Iron Rooster is trying to appeal to that inner deviant in all of us by serving breakfast food all day.

I craved some comfort food and indulged in Iron Rooster’s fried chicken and waffles option. It is one of their most popular meals, and what a combination it is!

The meat was fresh, flavorful, and crispy. It was also nice not to douse my waffles in syrup because they came pre-sweetened from the kitchen, unlike in most other restaurants.

The meal is very filling and will put you to sleep. It was comical how we had to push our morning plans since we were so satisfied that we just went home to nap.


Davis’ Pub

400 Chester Ave, Annapolis, MD 21403
Phone: 410-268-7432
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George Washington Davis started a confectionery and general store on the corner of 4th and Chester Avenue in the 1920s. It then turned into a lounge in the 1940s and then in 1986 became the Davis’s Pub that we see today.

It’s a cute dive bar for locals and doesn’t try to be anything too fancy. Davis’ pub is very much tied into the local community and hosts a series of regular festive events like pub crawls, tug of war, and trophy displays whenever a local sports team wins their league.

Our large group took advantage of “turkey platter night,” which typically happens on Wednesdays. Paired with some cold beers, this set the foundation for our fantastic night of fun.


Jalapenos

85 Forest Dr, Annapolis, MD 21401
Phone: 410-266-7580
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Gonzalo and Alberto are a talented duo keeping Mexican and Spanish traditional cuisine alive and Jalapenos. They have almost 50 years of experience working in the restaurant business between them.

The restaurant has some very die-hard patrons, and most of them would agree on how unfortunate it is that this joint is in a strip mall.

The surrounding is a little run down and does not match the high standards of both food and service at this restaurant. For anyone going there, I would highly recommend their tapas which come in generous sizes.


Café Normandie

185 Main St, Annapolis, MD 21401
Phone: 410-263-3382
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Café Normandie serves up nothing but pure ambiance! Well, they also serve food, but I’ll get to that in a second. The space is beautiful but in a very subtle way. It is the place to bring your girlfriend, boyfriend, spouse partner, or partner to be.

They are keen on sustainability and walk the talk by implementing practices like recycling vegetable oil, composting their organic waste, and using biodegradable materials where possible.

If you have a group no larger than 20, the restaurant will accommodate you in the upstairs area. Their surf and turf come highly recommended, plus the French onion soup and savory crepes.


Reynolds Tavern and 1747 Pub

7 Church Cir, Annapolis, MD 21401
Phone: 410-295-9555
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Reynolds Tavern is one of the oldest establishments in Annapolis, and this is very clear as you approach the old-style building exterior. It started in 1747 as a place where locals and travelers could come for food, drink, and stay overnight.

The host building has three levels, with the 1747 pub at the lowest level, two dining rooms on the next, and accommodation on the highest level.

They have a very calm outdoor space called the beer garden, and this is where I would recommend you find seats. The garden used to be a stable for travelers’ horses back in the day.

I would suggest that you try the English high tea. There is a misconception that this meal comes in tiny servings, but I was happy to be proved wrong by the sheer amount of finger foods.

Plus, it is interesting to learn about English tradition and why things were in those particular arrangements.


Sailor Oyster Bar

196 West St #2824, Annapolis, MD 21401
Phone: 410-571-5449
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The servers at Sailor Oyster Bar will leave you wondering if they’re acting and pretending to be super nice, but I assure you they are not. Friendly culture starts from the very top level of management, and they communicate the importance of individualized care to all staff members.

During my visit, I ordered the oyster chowder and found it delightful. I was having dinner with business associates who were new to the area, and they decided to try the merchant marine sandwich, which turned out to be a little too generous as they couldn’t finish it. Either way, they enjoyed every single bite!


Dry 85

193 B Main St, Annapolis, MD 21401
Phone: 443-214-5171
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Dry 85 takes a lot of design cues from the roaring twenties because it looks like an industrial space reminiscent of the prohibition era.

In a tongue-in-cheek way, I thought that that’s probably an explanation for their minimal outside seating space. You wouldn’t want to sip your illegal drink outside during the prohibition era, would you?

We ordered fried green tomatoes with a side of truffle fries, and they hit the spot! They also have an extensive beer selection and possibly every bourbon, so patrons have many options to enjoy.


Level a small plates lounge

69 West St, Annapolis, MD 21401
Phone: 410-268-0003
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The small plate dining concept was introduced in the US after 2001 but has had adequate traction. The idea behind it is ordering a series of foods that come on several small plates, which diners share at the table.

In addition to promoting a shared culture, it allows diners to be more adventurous while limiting their impatience because the food arrives in a staggered manner. Also, the small plate dining enables the restaurant to get creative.

I had a five-leaf cocktail that paired very well with my salmon. The small plate concept is not common, so I would encourage anyone unfamiliar to visit and try it.


Final Thoughts

From all of the suggestions, you can see that there are myriad choices when it comes to picking a restaurant in the Annapolis area.

Decide on a cuisine style and aesthetic that works for you, then go forth to explore! Happy dining!

If you think I left a restaurant out of this list, make sure to leave a comment, and I’ll check it out.

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Written by Erin Elizabeth

Erin lives in East Passyunk and enjoys checking out the local restaurants in South Philly and beyond. Her favorite restaurants are those with spicy food and outdoor seating so that she can bring along her dog, Miss Piggy.