Where to Eat & Drink in Annapolis

Headed to Annapolis for the U.S. Sailboat Show? Check out our favorite bars, pubs, watering holes, restaurants, and more.


September 25, 2019
Annapolis Main Street
Main Street, Annapolis Steinbrook Photography


Chick & Ruth’s
165 Main St
(410) 269-6737

Sophie’s Crepes
1 Craig St
(410) 990-0929

Happy Hour:

Boatyard Bar and Grille
Favorite of local sailors, happy hour and pint drinks.
400 4th St, Eastport
(410) 216-6206


McGarvey’s Saloon and Oyster Bar
The boat-show crowd hangout. Order the Maryland Crab Soup, French Dip, and Bloody Mary.
8 Market Space
(410) 263-5700

The Chart House
Best harbor view.
300 2nd Street, Eastport
(410) 268-7166

Ram’s Head Tavern
Best beer selection.
33 West Street
(410) 268-4545


Best margarita.
132 Dock Street
(410) 280-0028

Best painkiller.
80 Compromise Street
(410) 626-0004


Davis’ Pub
Best burger, and local sailor favorite.
400 Chester Avenue, Eastport
(410) 268-7432


Cantler’s Riverside Inn
Go by boat for the crabs!
458 Forest Beach Rd
By boat: On Mill Creek, off Whitehall Bay: a trip of two or three miles
(410) 757-1467

Severn Inn
Best river view.
1993 Baltimore Annapolis Boulevard
(410) 349-4000

Buddy’s Crabs & Ribs
Best crabs downtown.
100 Main Street
(410) 626-1100


Market House
Open late Friday and Saturday.
25 Market Space
(401) 263-7949

O’Leary’s Seafood
Best upscale seafood.
310 Third St
(410) 263-0884

Lewnes’ Steakhouse
Best steak and key lime pie.
401 Fourth St
(410) 263-1617

Best sushi, worth the walk! Make sure to order the moving Yomatos Tofu.
51 West St
(410) 990-9868

Fox’s Den
A fun gastropub right on Main Street. Try the pizzas!
179B Main Street
(443) 808-8991

Harvest Wood Grill + Tap
Farm to Table goodness, tapas style.
26 Market Space
(410) 280-8686

Middleton Tavern
Go for the oyster shooters
2 Market Space
(410) 263-3323

Awesome Thai food!
167 West Street
(410) 224-8424

The Blackwall Hitch
In Eastport; Great rooftop deck and live music 400 6th Street, Eastport
(410) 263-3454

Red Red Wine Bar
Convenient location right on Main Street, open late 189 Main Street (410) 990-1144

Interesting cocktails and tapas-style “small plate” food
69 West Street
(410) 268-0003

Vida Taco Bar
A new favorite for team CW. Great tacos and tequila selection.
200 Main Street
(443) 837-6521

Special thanks to Eddy Lavino and Tim Murphy for their suggestions!


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