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. Galway Bay Irish Restaurant and Pub

    $

    Step inside this Irish pub, and you'll be welcomed like a member of the family. As would be expected, the corned beef and cabbage and other traditional Irish menu items (along with classic Annapolis bar food like crab and oysters) are fantastic. The bread pudding served with vanilla custard is a great way to end your meal. On Sunday, brunch is served from 10 to 1:30—the homemade corned-beef hash is simply divine—and live Irish music is performed 4–8.

    63 Maryland Ave., Annapolis, Maryland, 21401, USA
    301-263–8333

    Known For

    • Traditional Irish grub and hospitality
    • Authentic homemade corned-beef hash
    • Sunday brunch with live music
  • 2. 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
  • 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. 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
  • 5. 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
  • 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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