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. Carrol's Creek Cafe

    $$$

    You can walk, catch a water taxi from City Dock, or drive over the Spa Creek drawbridge to this local favorite in Eastport. Whether you dine indoors or out, the view of historic Annapolis and its harbor is spectacular. Any of the entrées, including the herb-encrusted rockfish or grilled filet mignon, can be turned into a four-course meal with the addition of soup, salad, and dessert.

    410 Severn Ave., Annapolis, Maryland, 21403-2524, USA
    410-263–8102

    Known For

    • à la carte Sunday brunch
    • Upscale (but not too pricey) seafood specialties
    • Amazing city and harbor views
  • 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. Harry Browne's

    $$$

    In the shadow of the state house, this understated establishment has long held a reputation for quality food and attentive service that ensures bustle year-round, especially during the busy days of the legislative session (early January into early April) and special weekend events at the Naval Academy. The menu clearly reflects the city's maritime culture, but also has seasonal specialties. The sidewalk café is open, weather permitting, April through October.

    66 State Circle, Annapolis, Maryland, 21401-1906, USA
    410-263–4332

    Known For

    • Political clientele
    • Tasty homemade desserts, such as Oreo cheesecake
    • Champagne brunch on Sunday
  • 5. Preserve

    $$

    Jars of pickled chard stems and radishes, preserved lemons, and pepper jelly line the shelves at this lively spot on Main Street run by a husband-and-wife team who both have impressive culinary resumés and a shared passion for pickling, fermenting, and preserving. The chef's roots in the Pennsylvania Dutch country shine through with chicken potpie, pork and sauerkraut, and a Dutch hash and liverwurst sandwich.

    164 Main St., Annapolis, Maryland, 21401, USA
    443-598–6920

    Known For

    • Varied dishes that highlight unique preservation methods
    • Kimchi and sauerkraut galore
    • Lots of seasonal veggies

    Restaurant Details

    Rate Includes: Closed Mon. and Tues.
  • Recommended Fodor’s Video

  • 6. Vin 909 Winecafé

    $

    If it wasn't for the sign out front, you might think you're at someone's Eastport home, given the charming front porch and well-tended gardens. But walk through the doors, and you'll discover a casually hip and always crowded restaurant serving organic, sustainable, and seasonally focused food that's simply fantastic. The "plates" (bigger than appetizers and slightly smaller than entrées), like shrimp cassoulet, truffle sliders, and duck enchiladas, are excellent.

    909 Bay Ridge Ave., Annapolis, Maryland, 21403, USA
    410-990–1846

    Known For

    • Crispy pizza with farm-to-table toppings
    • Huge wine menu by the glass and bottle
    • Diverse selection of beers

    Restaurant Details

    Rate Includes: Closed Mon.

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