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Our Favorite Area Pubs & Clubs


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Cult Classic Brewery on Kent Island


49 West - 49 West St Annapolis, MD 21401 (410) 626-9796
Unique Coffeehouse, Winebar & Gallery with lite fare. A nice place to start out.
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Acme Bar and Grill - 163 Main Street, Annapolis, MD 21401 (410) 280-6486
Downtown bar that features live music for the younger crowd.
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Annapolis Smokehouse & Tavern - 107 Hillsmere Drive, Annapolis, MD 21403 (410) 571-5073
BBQ, Ribs, Wings, and more. Live music at night and a great Happy Hour.
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Armadillo's Bar & Grill - 132 Dock St., Annapolis, MD 21401 (410) 280-0028
Tex-Mex themed lower level and live music upstairs on most nights.
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Big Bats Cafe', 216 St. Claire Place / Benton's Crossing, Stevensville, MD 21666 410-604-1120
Sports Bar and Restaurant with tons of baseball memorabilia. Friendly service, great prices & lots of flat screen TVs to watch your favorite game. Live music from the best area bands, kareoke, trivia, large game room, and lots of night-time fun! Big Bats Cafe has an extensive menu with daily specials, great beer selection, children's menu, and the best wings anywhere! Large full-service outside bar and patio eating area too!
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The Blackwall Hitch - 400 Sixth Street, Annapolis, MD 21403 (410) 263-3454
Urban chic lounge and restaurant with a large varied menu that includes an oyster bar and Sunday brunch. Live acoustic music on weekend nights.
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Blackwater Distilling & Tavern, 405 Cleat Street, Stevensville, MD 21666 - (443) 249-3123
Email: info@blackwaterdistilling.com
Features award-winning distilled spirits, local craft beers & wine, and an outdoor patio with live music.
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Boatyard Bar & Grill - 400 4th St., Annapolis, MD 21403 (410) 216-6206
A taste of the keys with a boat themed bar. Located in Eastport.
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Castlebay Irish Pub

CastleBay Irish Pub, 193 Main Street, Annapolis, MD 21401 - (410) 626-0165
Downtown Irish Pub with a nice selection of beer and the best Guiness pour in Annapolis! A great place to meet up with friends. Live music on weekend nights and sometimes during the week.
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Chesapeake Brewing Company, 114 West Street, Annapolis, MD 21401 - (410) 268-0000
Micro-Brewery.
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The Crab Deck, Kent Island Narrows, Grasonville, MD - (410) 827-6666
The Crab Deck is a casual restaurant until around 8PM, when it turns over to a club. This is a building with open walls and a large deck on the Chesapeake Bay. There are usually live bands here Thursday through Sunday, and it gets quite crowded on weekends. The Crab Deck is open on rainy days too, they can seal up the building and keep the party going.


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Cult Classic Brewery on Kent Island

Cult Classic Brewing, 1169 Shopping Center Rd, Stevensville, MD (410) 980-8097
Large brew-pub that has craft beer along with a full bar, food, and live music venue with a great stage area.
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Davis Pub, 400 Chester Avenue, Annapolis, MD 21403 - (410) 268-7432
Very "local" pub with a fun atmosphere located in Eastport.
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Dry 85, 193B Main Street, Annapolis, MD 21401 - (443) 214-5171
Bourbon, beer, and gourmet comfort food.
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Dock Street, 136 Dock Street, Annapolis, MD - (410) 268-7278
Late night happy hours, live music, and food until 1AM.
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The Ebb Tide Tavern, 985 Bay Ridge Road, Annapolis, MD - (410) 280-2343
A locals bar that features dartboards, pool tables, and karaoke.


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El Jefe Mexican Kitchen and Tequila Bar, 1235 Shopping Center Rd, Stevensville, MD - 410-604-1234
Email: ElJefeMexKitchen@gmail.com
Not just great authentic Mexican food, but the bar side has live music by the area's best talent, great drink specials and promotions, and a friendly fun staff. You can't get a better mixed drink or Margarita anywhere! Bienvenidos Amigos!
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Fado Irish Pub, 1 Park Place, Annapolis, MD 21401 - (410) 626-0069
Chain restaurant / pub with an extensive menu.
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The Federal House, 22 Market Space, Annapolis, MD 21401 - (410) 268-2576
American menu and large pub that features live music and kareoke.
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Fox's Den, 179B Main Street, Annapolis, MD 21401 - (443) 808-8991
Gastro Pub with pizza, duck-fat fries, and a large selection of beer.


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Galway Bay, 63 Maryland Avenue, Annapolis, MD 21401 - (410) 263-8333
Irish Pub and Restaurant with the pub being completely seperate. Nice selection of beers.
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Grapes Wine Bar, 1410 Forest Drive, Annapolis, MD 21403 - (410) 571-5378
Small plates wine bar and more.
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Harry Brown's, 66 State Circle, Annapolis, MD 21401 - (410) 263-4332
The wine bar is upstairs and caters to a crowd that is a bit upscale and mellow. A great place to start out.
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Hemingways, 357 Pier One Road, Stevensville, MD 21666 - 410-827-4959
Restaurant and outdoor bar with great waterfront views and live music in-season.


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Heroes Pub, 3 Riverview Avenue, Annapolis, MD 21401 - (410) 573-1996
48 beers on draft make this the best beer selection in town. The only area pub to get a "Ressurection Ale'. Try the buffalo chicken strips too.
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Jalapenoes, 85 Forest Drive, Annapolis, MD 21401 - (410) 266-7580
Spanish / Mexican fine dining restaurant with a cozy bar.
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Jetty Dock Bar & Restaurant, 201 Wells Cove Road, Grasonville MD 21638 - (410) 827-4959
Hot Steamed Crabs and Cold Beer. Live bands Friday and Saturday night and Sunday afternoons.
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Kentmorr Restaurant & Crabhouse / Dirty Daves Island Tiki, 910 Kentmorr Rd., Stevensville, MD 21666 - (410) 643-2263
Waterfront dining. Hard Crabs, award winning crab cakes, fish specials, ribs, steaks and more. Come by car, boat, or plane and experince unforgettable food, bay views, and service!
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Level, 69 West Street Street, Annapolis, MD 21401 - (410) 268-0003
Small plates restaurant and lounge. Great service and upscale atmosphere.
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Luke's Grille, Thompson Creek Mall, Stevensville, MD - (410) 643-9435
Luke's Grille includes a full kitchen serving a full menu with a seperate dining section and a 40+ foot bar. Catch your favorite sports on their many large screen TV's. Live music on weekends.


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McGarvey's Saloon and Oyster Bar, 3 Market Space, Annapolis, MD 21401 - (410) 263-5700
Fun bar that has a very unique setting. Trees inside the building and an oyster bar located within the back space. Nice beer selection, especially the "Aviator Ale". Located right downtown, this is a perfect meeting place.
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Metropolitan Kitchen & Lounge, 169 West Street, Annapolis, MD 21401 - (410) 280-5160
Large menu and a roof-top bar with live music.
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Middleton Tavern, 2 Market Space, Annapolis, MD 21401 - (410) 263-3323
Historic taven with live music and a piano bar.
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Mike's Crabhouse, 3030 Riva Road, Riva, MD 21401 - (410) 956-2784
Laid-back casual bar with outside waterfront seating. Live music and kareoke on occasion.
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Mother's Penninsula Grille, 969 Ritchie Hwy, Arnold MD 21012 - (410) 975-5950
Great happy hour and live entertainment at night.
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O'Briens Oyster Bar, 113 Main Street, Annapolis, MD 21401 - (410) 268-6288
Night club with live music and dance music. Caters to the younger crowd.
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Old Stein Inn, 1143 Central Ave, Edgewater, MD 21307 - (410) 798-6807
German restaurant and bier garden.
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Pusser's Landing at the Marriott, 80 Compromise Street, Annapolis, MD 21401 - (410) 626-0004
Waterfront and outside bar overlooking City Dock.
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Ram's Head Road House, 1773 Generals Hwy, Annapolis, MD 21401 - (410) 849-8058
Burgers, sandwiches, regular trivia nights & live local music.


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The Ram's Head Shore House, 800 Main Street, Stevensville, MD (410) 643-2466
The Ram's Head Shore House has a great beer selection including their own tasty "Fordham" micro-brews. Popular happy hour with plenty of food freebies and cheap drinks, as well as live music on weekend nights.
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Ram's Head Tavern, 33 West Street, Annapolis, MD 21401 - (410) 268-4545
Microbrewery with a large menu, national acts, great local beers, and outdoor seating.
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Red Eyes Dock Bar, Kent Island Narrows, Grasonville, MD
Red Eyes Dock Bar is famous for its Sunday afternoon festivities! A lot of people hit Red Eyes on their way back from the Ocean to the DC and Baltimore area, and are primed for fun! Summer Sundays are a fun time. On weekend nights Red Eyes has live music. A great place to relax with a beverage under palm trees on a week day night, or dance under the stars to adult-oriented music on Friday and Saturday nights. During the winter months, the newly remodeled and enlarged upstairs becomes a sports bar.
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Red Red Wine Bar, 189 Main St, Annapolis, MD 21401 - (410) 990-1144
Wine bar with small plates and full menu.
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Riverbay Roadhouse, 1374 Cape St Claire Rd, Annapolis, MD 21409 - (410) 757-2919
Family restaurant with a large seperate bar area, big menu, and very good food.
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Sam's on the Waterfront, 2020 Chesapeake Harbour Drive East, Annapolis, MD 21403 - (410) 263-3600
Sam's on the Waterfront - 'Annapolis' hidden treasure" come and see where the locals eat and drink with live music on weekends dining inside and out!


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Stan & Joes Saloon, 37 West Street, Annapolis, MD 21401 - (410) 263-1993
Fun old-timey pub with an extensive menu, live music, and outdoor seating.
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Severn Inn, 1993 Baltimore Annapolis Boulevard, Annapolis, MD 21409 - (410) 349-4000
Waterfront restaurant / bar on the Severn River with a great view of the USNA. Casual quiet bar with great food.
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Tsunami, 51 West Street, Annapolis, MD 21401 - (410) 990-9868
Sushi restaurant / bar in a 'hip' atmosphere. Dance music on occasion.
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Vin 909 Winecafe, 909 Bay Ridge Ave, Annapolis, MD 21403 - (410) 990-1846
Farm-to-table New American menu and a large wine list.
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West End Bar & Grill, 2049 West Street, Annapolis, MD 21401 - (410) 266-7662
Lively pub that is a great place to catch a game.
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Yellowfin Steak & Fish House, 2840 Solomons Island Road, Edgewater, MD - (410) 573-1333
Waterfront Seafood Restaurant and Bar with a great happy hour.
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