Annapolis has more than 70 restaurants and eateries in the greater downtown area alone. Most restaurants in the Main Street and West Street areas post their menus and prices outside the door. If Main Street is a bit crowded, walk up to West Street (near the state capitol). There are also a few places on the side streets.

Below are the Eats & Drinks places that locals mentioned when we asked around. This is not a “best of” — there are other websites that specialize in reviews — nor is it paid advertisement. We simply went into town, talked to people, and stopped by. Here’s what we found:

Crab Cakes

Annapolis is proud of its Maryland crab cakes and finding the best depends on who you ask. Crab cakes vary most on the type of crab (Maryland vs. Alaskan/others) and the amount of filler. Maryland crabs rarely make the big, lumpy crab cakes that many like. Nearly every restaurant in historic Annapolis serves crab cakes, but here are the places locals recommend.

Dock Street Bar (136 Dock Street) is probably mentioned most. It’s right by City Dock in a historic brick building. It’s long, narrow, and dark, with a few tables outside.

Acme Bar & Grill (163 Main Street) is a dive bar that specializes in crab cakes and cheesesteaks, but its crab cakes come highly rated. Because of its divvy-ness, many tourists avoid it and Acme often has seats when other places don’t.

Chick & Ruth’s Delly (165 Main Street) is basically a diner on Main Street. It has the grill and milkshakes, but it’s known for its inexpensive (in comparison to other places) crab cakes. This is a popular place; expect a wait.

Wild Country Seafood (124 Bay Shore Avenue) is where you’ll find the traditional crab cakes made from Maryland crabs, similar to what you get on Smith and Tangier Islands. The crab bits are smaller and delicate taste. They’re also a great bargain. The local seafood market is in Eastport near the Annapolis Maritime Museum at the end of a short dead-end street. There’s only stool seating inside along the window and picnic tables outside. Hours vary depending on season and availability of seafood. The family catches it themselves in the morning and sell it in the afternoon.

A Short Drive Away

Edgewater Restaurant (148 Mayo Road, Edgewater, MD) is the alternative when locals argue about who has the best crab cake. It’s across the South River from Annapolis, but close enough to include. It’s a mom & pop kind of place, simple and not fancy.

Maryland Crabs

If you want crabs in downtown Annapolis, there’s Buddy’s Crabs & Ribs (100 Main Street), which caters to the tourist crowd and is a busy place during the summer. It’s on the second floor of a corner building and has big windows facing City Dock. Buddy’s is also known for it’s all-you-can-eat seafood buffet.

A Short Drive Away

The place locals mention most for cracking crabs is Cantler’s Riverside Inn (458 Forest Beach Road) on Mill Creek. Cars will line up on the road waiting for parking in the small lot. There’s a small dock for boaters. Patrons share long paper-covered tables inside or outside. If you walk down the steps to the water, you’ll see the large tanks where they keep the live, locally caught crabs.

Then, there’s Mike’s Crab House (3030 Riva Road) on the South River. It’s a huge place with seating inside and outside. It has a larger parking lot and a bigger boat dock. It’s a constant argument on which has better crabs, Cantler’s or Mike’s.

Another option for crabs is the seafood markets. These places sell live or cooked crabs for take-out. They’ll cook the crabs when you arrive. The larger shops sell local, and shipped-in, seafood, among them Annapolis Seafood Market and Joe’s Seafood (403 Richie Highway, Severna Park).

But there are a number of small shops run by local watermen. Rey’s Crabs (363 Richie Highway, Severna Park) is one. It’s best to call ahead if you want large or extra-large and reserve crabs. Those are sold quickly. And Rey’s closes when the crabs are sold for the day.

Across the Bay Bridge from Annapolis, on Kent Island, there are a number of large crab houses. Take the Kent Narrows Road exit off Highway 50 and you’ll find large restaurants on either side of the highway. Which is the best depends on who you ask.


Oysters in Annapolis usually come from the Chesapeake Bay, but not always. The oyster season varies in Maryland and Virginia, so oysters can come from either state and the saltiness depends on where the oysters come from in the Bay. If oysters are out of season locally, or they’re looking for variety, restaurants will reach out to other areas.

In downtown Annapolis, Middleton Tavern (2 Market Space) and McGarvey’s Saloon (8 Market Space) are well-known for their raw bars. They’re historic pubs next to each other by City Dock.

In Eastport, a neighborhood across Spa Creek, the Boatyard (400 4th Street) has a notable raw bar, and happy hour oyster prices. It fills up during happy hour and after boating events.

Ice Cream & Fudge

Annapolis Ice Cream Company (196 Main Street) is a local favorite that specializes in unique flavor combinations. The ice cream is made daily in the store. It may be a little pricier than other shops, but the scoops are generous and you can get two flavors in one scoop.

Storm Brothers Ice Cream Factory (130 Dock Street) is run by two brothers and has been in the same location since 1976. They have 46 flavors, featuring Turkey Hill ice cream. Be prepared to wait in line on summer days. They only take cash, but there’s an ATM in the store.

Several shops along Main Street make their own fudge and candy. Uncle Bob’s Fudge Kitchen (112 Main Street) is a local shop that makes fudge & brittle and bakes cookies daily in an old general store stuffed full of tourist trinkets.

Kilwins (128 Main Street) is a franchise out of Michigan. The fudge and some candy are made in the Annapolis kitchen in the front of the store; the ice cream and packaged candy are made in Michigan for the Annapolis store.

Waterfront Dining

The restaurants on the water, or with a water view, in Annapolis tend to be a bit pricier, but they often have a few cheaper selections. They’re casual dress during the day and dressier at night.

Pussers Caribbean Grille (80 Compromise Street) is a short walk around City Dock. It has a long row of outside tables along the water and is a popular stop for boaters.

Carrol’s Creek Cafe (410 Severn Avenue) is in Eastport, across Spa Creek. If you’re walking, it’s tucked behind boat builders & repair shops. If going by boat, it’s in Annapolis City Marina. Look for a bright red awning. Carrol’s Creek is known for its range of good food. Inside is fine dining, while outside offers a cheaper menu featuring sandwiches.

Chart House (300 2nd Street) is located in a former shipyard boathouse overlooking the Severn River. It’s on the Eastport side of Spa Creek and a prime spot to watch sailboat races during boating season. The Chart House has only indoor seating and is considered higher-end dining.

Blackwall Hitch (400 6th St, Annapolis, MD 21403), located in the Eastport section of Annapolis, isn’t on the water, but you can see the water from its open-top roof. The name comes from a knot used by seamen to allow them to unload cargo quickly and there’s a modern-natical theme throughout the restaurant/bar. They specialize in creative seafood. Prices range from $12 for burgers to $32 for rockfish and crab dinners. 

A Short Drive Away

Severn Inn (1993 Baltimore Annapolis Boulevard) is on the other side of the Severn River from the Naval Academy. It’s not an inn, just a restaurant. It does have a large outdoor seating area on its dock, and a wall of windows for those sitting inside, facing a great view of the river and Naval Academy. There is a different menu for inside and outside, with inside being fine dining and outside offering sandwiches and “baskets” if you ask for the pub menu.

Sam’s on the Waterfront (2020 Chesapeake Harbour Drive East) is part of a marina off the Chesapeake Bay, just south of the Severn River, and can be reached by car or boat. Sam’s chef is a local favorite. If you go by car, it’s in a condo development. Just let the guard at the gate know you’re going to Sam’s and they’ll give you a free parking pass and point you in the right direction. If going by boat, call ahead to check dock availability.

Libby’s Coastal Kitchen (357 Pier 1 Rd, Stevensville) is on the other side of the Bay Bridge from Annapolis and has a spectacular view of the bridge and sunsets. It has a large outdoor seating area and wide windows if you decide to stay inside. If going by car, it’s the first exit off Highway 50 once you cross the bridge. There’s a $6 one-way fee to cross the bridge. If traveling by boat, docking is available at Bay Bridge Marina.

Dining in an Historic Place

Middleton’s Tavern (2 Market Place) is one of the oldest continually operating taverns in the United States. In 1750 it was an “Inn for Seafaring Men.” George Washington, Thomas Jefferson and Ben Franklin were among the patrons when the Continental Congress met in the State House (1783-84).

Reynolds Tavern (7 Church Circle) was built in 1747 to house a hat business, inn, and tavern. Those doing business at the state capitol — farmers, gentlemen, merchants, and soldiers — met there. They still do actually. The pub is in the basement in what used to be the kitchen. (They serve pub food.) There’s a tea room on the first floor. If going for the tea, a reservation is a good idea. The second floor serves as an inn. It also has a popular outdoor patio.

The Treaty of Paris is the restaurant in The Maryland Inn (16 Church Circle), built in 1695 as a house for the governor at the time. Over the years, it was expanded into an inn. This is a locals’ go-to for special occasions. There’s a small, intimate pub in the basement called the Drummer’s Lot that has a cheaper pub menu.  They say Ben Franklin had a lager there once with John Adams.

Cheap Eating

MarketHouse next to City Dock is a former farmer’s/watermen’s market now turned into sandwich and take-out shops. It has sandwiches, salads, soups, crab cakes-to-go and ice cream. There’s stool seating facing the window and some tables outside, but you can take your sandwich across the street and sit on the cement benches overlooking City Dock. MarketHouse also has public restrooms and an ATM.

Pip’s Dock Street Dogs (118 Dock Street) is a small hotdog counter next to City Dock that also sells cheese steaks and burgers. The focus is specialty dogs with 25 mustards to choose from. It can be a squeeze inside with some stools facing the window and a few tables outside. Pips is closed on Mondays during the winter.

Chick & Ruth’s Delly (165 Main Street) is a diner in the middle of the hill on Main Street. It serves sandwiches and milkshakes. The small restaurant is popular and often has a line of people waiting.

Boatyard (400 4th Street) is across Spa Creek from City Dock, about a 10 minute walk. It’s a bar/restaurant known for its local seafood, but locals go there for happy hour oyster prices. It fills up during happy hour and after boating events. It’s nice, but casual. It’s also know for weekend brunch.

Also in Eastport, Davis’s Pub (400 Chester Avenue) is a small neighborhood hangout with outside picnic tables. It’s a big local favorite for burgers, but they have standard pub grub. The appetizer specialty is crab balls and crab pretzels. It gets packed after sailing races & other local sporting events. There’s a nice little waterfront park across the street that’s a good place to wait for a table.

A Short Drive Away

Heroes Pub (1 Riverview Avenue) is a bit tricky to find and requires a car. It’s a dive bar known for its cheap beer and steamed shrimp, as well as hefty sandwiches. The pub caters to firemen, police, and other first responders in general, thus the name.

Irish Food

Annapolis has an unusually large number of Irish pubs for a town its size. That could be due to the town’s colonial start. Here are some known for their food.

Galway Bay (63 Maryland Avenue) has traditional Irish fare (corned beef, shepherd’s pie, etc.) as well as crab cakes. On Sundays, they have a jazz brunch.

Castlebay (193 Main Street) serves traditional Irish food but has a locally-known chef who creates non-Irish specialties featuring crab and other seafood. They serve sandwiches until 5pm; oh, and brew their own beer.


Annapolis also has a number of sushi restaurants, probably because folks expect seafood when they visit the Chesapeake Bay port. Favorite sushi is like asking locals about their favorite Irish bar — there’s no consensus, but here are some notable ones.

Joss Cafe & Sushi Bar (195 Main Street) is a small cafe with a sushi-bar twist.

Sakura Cafe (105 Main Street) specializes in unique combinations in its rolls.

Nano Asian Dining (189 Main Street) is a traditional sushi restaurant with stool seating by the sushi maker and tables along the wall.

Tsunami (51 West Street) is a funky place popular with the hipster crowd. It specializes in inexpensive sushi and specialty cocktails.

Wine Selection

By the Glass…

Red Red Wine Bar (189 Main Street) has a funky, eclectic decor and sells 46 wines by the glass and several wines on tap. Along the same line is Crush Kitchen & Winehouse (114 West Street). It’s in a former firehouse and sells by glass, half-glass, flights as well as bottle.

In the Eastport neighborhood, across 6th Street and up Bay Ridge Avenue, you’ll walk through a quaint neighborhood with a quirky mix of older homes and boutiques to find Vin 909 (909 Bayridge Avenue), a popular wine cafe.

By the Bottle…

If you want a bottle of wine to take back to the boat, Mills Fine Wine and Spirits (87 Main Street) has a large selection of quality wines. They also have a large selection of craft beers and a beer shelf from which to create your own six-pack.

Beer Selection

Nearly every pub in downtown Annapolis, Maryland Avenue, and uptown on West Street features a large, rotating selection of micro & craft beers. There are several Irish pubs featuring Irish and English brews. Each pub has fierce supporters. Most bars have TVs for watching sports (especially Navy games). Galway Bay (63 Maryland Avenue) is proud to not have a TV; this is a conversation bar.

On West Street, Rams Head (33 West Street) features English beers, while Stan and Joe’s (37 West Street) is big on regional beers on tap.

Digiprove sealCopyright secured by Digiprove © 2018-2022