Annapolis Travel Guide

USA  #9 in Best Cheap Summer Vacations
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What to Eat in Annapolis

Owing to its idyllic perch on the harbor, you might guess that dining in Annapolis would be seafood-heavy. And you'd be right. Steamed crabs, in particular, are one of the city's specialties, and you can try them at any number of restaurants. Mike's Crab House and Cantler's are among some of the old favorites. For ice cream, the Annapolis Ice Cream Company is an unparalleled spot. If you're looking for a wine bar, you might try the well-reviewed Vin 909 Winecafe. Chick & Ruth's Delly is legendary, namely for their "colossal challenges," which involve downing a 6-pound milkshake or munching your way through a 3-pound sandwich. 

Find the Best Restaurants in Annapolis

  • #1
    Annapolis Ice Cream Company
    #1 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 736 reviewsTripAdvisor (736)
    $ | American
    Main Street, Annapolis, MD 21401
    Read More »
  • #2
    Vin 909 Winecafe
    #2 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 668 reviewsTripAdvisor (668)
    $ - $$ | American, Pizza, Wine Bar
    909 Bay Ridge Ave, Annapolis, MD 21403-3029
    Read More »
  • #3
    Dry 85
    #3 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 210 reviewsTripAdvisor (210)
    $ - $$ | American, Bar, Pub
    193B Main St, Annapolis, MD 21401-2006
    Read More »
  • #4
    Jalapeno's
    #4 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 521 reviewsTripAdvisor (521)
    $ - $$ | Mexican, Latin, Spanish
    85 Forest Drive Forest Plaza, Annapolis, MD 21401-3716
    Read More »
  • #5
    O'Leary's Seafood Restaurant
    #5 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 404 reviewsTripAdvisor (404)
    $$ | American, Seafood, Contemporary
    310 Third St Eastport, Annapolis, MD 21403-2510
    Read More »
  • #6
    Sofi's Crepes
    #6 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 209 reviewsTripAdvisor (209)
    $ |
    1 Craig St, Annapolis, MD 21401-1801
    Read More »
  • #7
    Boatyard Bar & Grill
    #7 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1582 reviewsTripAdvisor (1582)
    $ - $$ | American, Bar, Seafood
    400 4th St, Annapolis, MD 21403-2504
    Read More »
  • #8
    Iron Rooster Annapolis
    #8 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1276 reviewsTripAdvisor (1276)
    $ - $$ | American, Bar
    12 Market Space, Annapolis, MD 21401-1816
    Read More »
  • #9
    Osteria 177
    #9 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 512 reviewsTripAdvisor (512)
    $$ | Italian
    177 Main St, Annapolis, MD 21401-2006
    Read More »
  • #10
    Mason's Famous Lobster Rolls
    #10 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 285 reviewsTripAdvisor (285)
    $ - $$ | American, Seafood, Fast Food
    188 Main St, Annapolis, MD 21401-2008
    Read More »
  • #11
    Kilwins
    #11 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 205 reviewsTripAdvisor (205)
    $ | American
    128 Main St, Annapolis, MD 21401-2003
    Read More »
  • #12
    Lewnes Steakhouse
    #12 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 431 reviewsTripAdvisor (431)
    $$ | American, Steakhouse
    401 4th St, Annapolis, MD 21403-2503
    Read More »
  • #13
    Light House Bistro
    #13 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 80 reviewsTripAdvisor (80)
    $ - $$ | American, Bar, Cafe
    202 West Street, Annapolis, MD 21401
    Read More »
  • #14
    Miss Shirley's Cafe
    #14 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 645 reviewsTripAdvisor (645)
    $ - $$ | American, Cafe
    1 Park Pl, Annapolis, MD 21401-3475
    Read More »
  • #15
    Davis Pub
    #15 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 266 reviewsTripAdvisor (266)
    $ - $$ | American, Bar, Pub
    400 Chester Ave, Annapolis, MD 21403-3205
    Read More »
  • #16
    Carrol's Creek Cafe
    #16 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1320 reviewsTripAdvisor (1320)
    $ - $$ | American, Seafood, Soups
    410 Severn Ave, Annapolis, MD 21403-2524
    Read More »
  • #17
    Chick and Ruth's Delly
    #17 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 1834 reviewsTripAdvisor (1834)
    $ | American, Diner
    165 Main St, Annapolis, MD 21401-2064
    Read More »
  • #18
    Level - a small plates lounge
    #18 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 355 reviewsTripAdvisor (355)
    $ - $$ | American
    69 West St, Annapolis, MD 21401-2426
    Read More »
  • #19
    Galway Bay
    #19 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 724 reviewsTripAdvisor (724)
    $ - $$ | American, Irish, Bar, Pub
    63 Maryland Ave, Annapolis, MD 21401-1629
    Read More »
  • #20
    Dock Street Bar & Grill
    #20 of 395 Places to Eat in Annapolis
    TripAdvisor Traveler Rating 4.5 based on 339 reviewsTripAdvisor (339)
    $ - $$ | American, Bar, Seafood, Pub, Gastropub
    136 Dock St, Annapolis, MD 21401-1803
    Read More »

Explore More of Annapolis

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