Annapolis and Southern Maryland Restaurants

In the beginning, there was crab: crab cakes, crab soup, whole crabs to crack. These days, most likely because of overfishing and habitat changes, crabs from the Bay are pretty scarce. Maryland's favorite crustacean is still found in abundance on menus, but most arrive from out of state. In addition, Annapolis has broadened its horizons to include eateries—many in the historic district—that offer many sorts of cuisines. Dinner reservations in Annapolis are recommended throughout summer and at times of Naval Academy events.

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  • 1. 49 West Coffeehouse, Winebar, and Gallery

    $$

    In what was once a hardware store, this casual eatery has one interior wall of exposed brick and another of exposed plaster; both are used to hang art for sale by local artists. Daily specials are chalked on a blackboard and include a large cheese-and-pâté plate, flatbread pizzas, deli sandwiches, espresso, waffles, soups, and salads.

    49 West St., Annapolis, Maryland, 21401, USA
    410-626–9796

    Known For

    • Live music every night
    • Eclectic coffeehouse vibe
    • Flatbread pizzas, deli sandwiches, and coffee galore
  • 2. Chick and Ruth's Delly

    $

    Deli sandwiches (many named after local politicians), burgers, subs, crab cakes, and milkshakes are the fare at this very busy counter-and-booth institution. Baltimoreans Ruth and Chick Levitt purchased the building, built in 1899, in 1965. Their son Ted and his wife, Beth, continue the business today. Don't plan on placing an order at 8:30 am on a weekday or 9:30 am on a weekend—that's when the place stops to say the Pledge of Allegiance.

    165 Main St., Annapolis, Maryland, 21401, USA
    410-269–6737

    Known For

    • Giant milkshakes (including a 6-pounder)
    • Patriotic decor and a daily recitation of the Pledge of Allegiance
    • Homemade pies and breads
  • 3. Metropolitan Kitchen & Lounge

    $$

    One of the few restaurants in the city with a rooftop, this establishment co-owned by Annapolis mayor Gavin Buckley takes full advantage of its lovely perch and features live music most evenings. The menu satisfies global palates in a town otherwise known for Old Bay and crab cakes, bringing in a bit of Australian flair from the mayor's homeland.

    175 West St., Annapolis, Maryland, 21401, USA
    410-280–5160

    Known For

    • Lamb burgers and traditional Greek salad
    • One of the few rooftop bars in town
    • Craft cocktails

    Restaurant Details

    Rate Includes: Closed Mon.
  • 4. Neptune's

    $$

    Modest Neptune's claims of preparing "the world's best mussels" rings true with many, making the trip to this tiny town just north of Chesapeake Beach worthwhile. Attached to the small bar, a glass-enclosed dining room with a brick floor is a friendly, informal spot to dig in to its signature dish—it's also a great place for nice views. Also on the menu are seafood pastas, burgers, and cuts of Angus beef. Don't let the "divey" atmosphere dissuade you; order the mussels (sold by the pound) and enjoy. This is the best restaurant (and there are few choices) in town.

    8800 Chesapeake Ave., North Beach, Maryland, 20714, USA
    410-257--7899

    Restaurant Details

    Rate Includes: Credit cards accepted
  • 5. Old Fox Books and Coffeehouse

    $

    With a carefully selected collection of new and used titles, this store is an oasis from the ubiquitous chains, and its café is a local favorite spot for an espresso drink or freshly baked pastry. After a bite, head outside to see the charming Fairy Garden and book house, which is literally made of books.

    35 Maryland Ave., Annapolis, Maryland, 21401-1627, USA
    410-626–2020

    Known For

    • Popular meeting spot for locals
    • Coffee drinks made with beans from local roaster, Ceremony Coffee
    • Annual Harry Potter birthday party
  • Recommended Fodor’s Video

  • 6. Rams Head Tavern

    $

    This traditional English-style pub serves better-than-usual tavern fare, as well as more than 100 beers—30 on tap—including five Fordham beers and others from around the world. Brunch is served on Sunday, and nationally known folk, rock, jazz, country, and bluegrass artists perform most nights.

    33 West St., Annapolis, Maryland, 21401-2420, USA
    410-268–4545

    Known For

    • Maryland cream of crab soup
    • Massive beer menu
    • Live music

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