Annapolis, Maryland is a historic city, home to the naval academy, and is Maryland’s capital city.
It’s famous for its seafood and crab cakes, and amazing waterfront restaurants, where tourists and locals alike come to kick their feet up and sit back and waste the day away, as boats both big and small sail around the Chesapeake Bay.
Most of the best restaurants in the Annapolis area are in the downtown waterfront area and on West Street, but there are plenty of great spots away from the popular tourists’ destinations.
In this list, we’ve detailed the 10 best Annapolis restaurants.
Lewnes’ Steakhouse
$$$$ | (410) 263-1617 | WEBSITE
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This chophouse is revered for its prime meat cuts while offering its visitors a lengthy wine list, cozy yet sophisticated, retro booths, and attractive, subdued lighting.
Lewnes’ family Steakhouse has been serving delicious food out of this location since 1921 and boasts the distinction of being the first Annapolis restaurant to feature U.S. Prime Steaks on its menu.
Their meat takes quite the journey before arriving at your plate, and they are more than happy to let you know about it. As far as great steak restaurants are concerned, this place checks off all the boxes.
It’s one of those restaurants that encapsulates that Annapolis charm, expensive suits next to sailors fresh from a voyage.
Galway Bay Irish Restaurant and Pub
$$ | (410) 263-8333 | WEBSITE
Galway Bay Irish Restaurant and Pub was first opened in 1998 and has quickly become a well-known favorite of the Annapolis traditions.
Proudly built on fine Irish hospitality, owners Michael Galway and Anthony Clarke, brought along their long-time team of dedicated service veterans, working together for more than 10 years, and have worked tirelessly to set a new standard for how a real Irish pub and restaurant is measured and judged.
The Galway Bay Irish Restaurant and Pub hold the distinct honor of being recognized as the Best Irish Pub every year since 2000, having the Best Bartender in 2016, the best place for Trivia Night, has been featured on the popular TV show Diners, Drive-ins, and Dives, and in 2019 was chosen by Irish Hospitality Global as the pub with the Best Irish Whiskey Experience in the United States.
O’Learys Seafood Restaurant
$$$ | (410) 263-0884 | WEBSITE
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O’Learys Seafood Restaurant is a long-time Annapolis favorite, serving fresh, upscale seafood in an old house adorned with colorful and abstract art.
Often mentioned amongst the best seafood restaurants in town, O’Leary’s does have solid seafood options on their menu, but what really keeps people coming back for more, are their specials where they frequently feature new fresh fish options and delectable seafood dishes.
The kitchen is very consistent and every dish on the menu is delicious. It’s worth walking a few blocks away from the bustling downtown scene and heading over to Eastport.
This is the perfect date night spot and is always sure to impress with both quality and quantity.
Hero’s Pub
$ | (410) 573-1996 | WEBSITE
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Hero’s Pub is a firehouse and police-themed bar that features a large draft beer selection and live music on a nightly basis with casual seafood, burgers, excellent wings, and a chill spot for darts and a few arcade games.
They are an excellent, small, joint, in a remote, less crowded, location in the Annapolis area. Hero’s is the perfect place to go with friends to watch your favorite football team and enjoy many other sports games at the same time.
They have a very good beer selection, and a hospitable atmosphere. They feature some of the friendliest staff in Annapolis and really feel like a community. The service is casual, fast, reliable, and always on point.
Level – a small plate lounge
$$ | (410) 268-0003 | WEBSITE
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Level – a small plate lounge, was first established with the goal in mind to become a spot that inhabited the “locals first” atmosphere, but also with a welcoming attitude to all.
Perhaps the most impressive aspect of this restaurant experience is their handcrafted cocktails with fresh juices, mixes, and garnishes.
Their commitment to source as many fresh ingredients locally from the State of Maryland and surrounding markets is admirable and certainly feeds into the “locals first” nature of this popular spot.
Level is dedicated to supporting the surrounding community of small businesses, watermen, farmers, and the sustainability of the environment, and this is a great place to spend your money while enjoying great conversation.
The small plate style of dining encourages sharing and brings a sense of deep focus and ingenuity that goes into each dish.
Stan & Joe’s Saloon
$ | (410) 263-1993 | WEBSITE
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Stan and Joe’s Saloon is the local hangout on West Street in Annapolis, MD. This neighborhood hangout is a great place to grab a beer, some small bar grub, kick back, and watch a game.
Some nights, they feature live music from local bands. This place is revered by locals for its lively and fun atmosphere, for the conversations you’re sure to have, and for the people you’re bound to meet.
Cozy and hospitable are the two most frequently used words attached to this down-to-Earth Saloons reputation and is a favorite of many in the community.
There isn’t much to say about Stan and Joe’s Saloon that hasn’t been said before, so make sure to stop in for a beer and a smile if you ever find yourself on West Street.
Reynolds Tavern and 1747 Pub
$$ | (410) 295-9555 | WEBSITE
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The Reynolds Tavern and 1747 Pub is quite possibly one of the coolest and most unique bars in Annapolis, Maryland. It is located downstairs, inside of the original kitchen and the ‘Hat Shop’ of its original founder, William Reynolds.
It has a cellar vibe to it, where the visitor enjoys two connected rooms underground, with a combination of stone and brick walls, complete with a fireplace (located in the bigger of the two rooms), short ceilings, brick flooring, and still has the original stairs from the first construction in 1737. This old-school tavern is a cozy spot for lunch, dinner, happy hour, or a drink with friends where guests are happily invited into a glimpse of history.
They open their beer garden in spring, summer, and early fall where they offer live music, outdoor movie screenings, and space where the Annapolis Shakespeare Company performs.
Rams Head Tavern
$$ | (410) 268-4545 | WEBSITE
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Rams Head Tavern makes this list as one of, if not the, most fun places in Annapolis to be. This traditional-style pub serves amazing crab dip, burgers, and some tasty salads.
While the food is fantastic, the real reason most people come here is for the always reliable and vast beer selection.
Their outdoor patio section is great when the weather calls for it, and the must-see basement or cellar area downstairs gives its visitors a unique, cozy, colonial vibe. Located right next door to their music venue, Rams Head Live, this pub is the perfect place to grab a quick bite to eat and a drink before or after a live show.
Armadillos Restaurant
$$ | (410) 280-0028 | WEBSITE
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Armadillo’s Restaurant, to put it simply, is an awesome little joint. It is in one of the older buildings in the Downtown Annapolis area, so it inherently radiates character.
The inside dining area can be a little tight, as it is inside a very narrow space.
One of the biggest perks of this restaurant is their specials on the main brand big cans of beer, but that’s not to say that their food isn’t exceptional, because it certainly is.
They have all the great bar food you can expect, with the Maryland twist, of course, piled high with crab meat and doused in the famous old bay seasoning.
Armadillos is a great fit for people watching being down on the City Dock, and you are sure to always have a great time.
Latitude 38° Annapolis
$$$$ | (667) 204-2282 | WEBSITE
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Latitude 38 Waterfront is in Downtown Annapolis at the end of the City Dock.
They offer super comfortable first-floor lounge seating with an amazingly decadent happy hour on partial outdoor deck seating with awesome views of the harbor and an elegant, white tablecloth.
The upper dining room is great for small to medium to large-sized party dining and is happy to serve a wide variety of banquet needs.
Latitude 38 also offers an exciting rewards membership club they call “Club 38” that gives members access to free wine, discounts on all drinks, discounts on food, free wine tastings, and free members-only happy hours.
This is the go-to spot for waterfront dining in a posh space and with an upscale attitude.
