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. Iron Rooster

    $

    There's often a line of hungry diners waiting for a table at this comfort-food haven located on the city dock, where the portions are generous, and the service is first-rate. You can enjoy breakfast all day—Benedicts and omelets are top sellers, as are the chicken and waffles and the shrimp and grits. If you've saved room for dessert, try the homemade peanut butter cup or the "shortcake" made with a Belgian waffle and topped with ice cream, strawberries, and whipped cream.

    12 Market Space, Annapolis, Maryland, 21401, USA
    410-990–1600

    Known For

    • Daily homemade Pop-Tart specials
    • Southern-inspired all-day breakfast (including amazingly light-and-fluffy biscuits)
    • Long lines
  • 2. 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
  • 3. 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
  • 4. Rod 'n' Reel

    $$

    This family-owned restaurant opened optimistically in 1936, the year after the demise of the railroad from Washington. Since then it has remained synonymous with superb seafood. Now part of the Chesapeake Beach Resort & Spa, its bay-side location still provides stunning views. The extensive menu includes succulent southern Maryland specialties such as rockfish stuffed with crab imperial, fried oysters, and the region's ubiquitous crab cakes.

    4165 Mears Ave., Chesapeake Beach, Maryland, 20732-5116, USA
    410-257--5596

    Restaurant Details

    Rate Includes: Credit cards accepted
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