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Happy Hour in Annapolis – So Many Choices!

We get a lot of requests asking for our favorite places to eat in Annapolis, which we’ve now collected in another blog.

We have a different category to consider – Happy Hour!  We’ve spent many nights grazing around downtown Annapolis (DTA), so we wanted to share the list with you.  As always, we’ll listen to guest feedback and add your own experiences.

Before we get to the list, if you aren’t a guest with us, please have a look at our web site, we’d love to have you stay with us. We include parking on site (other hotels ding you $29/night) and hot cooked breakfast ($20-30/day or more elsewhere).

Our location can’t be beat we are across from Naval Academy gate 1 (main entrance) and 2 blocks to city dock!  You can book direct with us, click here   …. Plan ahead and book early for your next visit, we fill up fast….


Fox’s Den – Weekdays 5:00-6:00pm: $4 off pizza/moules & frites; $3 off house cocktails; $2 off beers/wine by the glass, $10 brick oven pizza Mondays, Wednesday wine special – Order bottle of wine get food item for free.  The pizzas are inventive, fresh and filling!

Dock St. –  Happy Hour every day 4-7pm , Monday $7 Burger/$5 Wings (1/2 price), Tuesday $5 off crab cake sandwich (Top 5 crab cake in town), Wednesday $8 Tacos – Fish or Shrimp

Galway Bay –  Monday: Burger Night, Tuesday: Trivia Night, Wednesday – Irish Music Sessions in the Bar, Sunday – Brunch Menu 10:00-1:30, Entertainment often 4-8p

1747 Pub (Reynolds Tavern) – Sunday – Friday Happy Hour 4-7p.  Wednesday $6 burger night. Thursday night 1/2 price wines. Great Colonial setting

Iron Rooster – Mon-Fri 3-7p House red/white $5, Iron crush $5, draft of the day $5, 1/2 price apps.  You can easily make a meal of 2-3 apps/couple! 1/2 price burgers Monday 4p – close with purchase of a drink. See Robert at front desk or Virginia in the bar and tell them Flag House Inn sent you!

McGarveys – Mon – Fri 2-6 pm – $5 Wines, Beers and Single Liquor Drinks, $8 Signature Appetizers – Crab Pretzel, Calamari, Mussels, Clams Casino, Oysters Rockefeller, Steamed Shrimp, Nachos and Wings. Famous for Navy alumni & post wedding hang out.

Vida Taco Bar – Taco Tuesday 20% off Tacos. Check web site or sandwich board out front for other days.  Great creative tacos

Latitude 38 –  Happy hour goes late, 4-8p.  At the bar only.  1/2 price apps, discounted drinks.  Try crab deviled eggs, Tuna Nachos or spicy crab balls… Mon – Build a burger, Tu – Shrimp night, Wed – 1/2 off bottle of wine, Thu – $4 Sangria & Tito’s

Middletown Tavern – Mon – Fri 3 – 7p in the bar or lounge – discounted drinks, $5 apps, $1.50 oyster shooters – see full menu here

Preserve – 3-5p Tuesday-Sunday. $5 selected drinks, specials menu.  One of favorites in DTA. Farm to table/pickling/fermentation

Dry 85 – cocktail & beer specials Monday – Friday 3-6 pm – Draft of the day $5, Well drinks $5, bottled beer $3, selected apps $3-$6.

Red Red Wine – 3-6 pm Mon-Fri – $5 crab dip, $5 red/white/sangria of the day, $3 draft of the day. Huge wine selection, flights. Best wine bar downtown. Outdoor seating.

Pusser’s (Waterfront Hotel) – 4-7 pm Mon-Fri. – Reduced prices on apps & drinks.  Can get very crowded but can’t beat the view of the parade up and down Ego Alley

West St

Sailor Oyster Bar (SOB) – Happy House Tuesday – Friday 4-530 pm, Saturday 12n-3p, Sunday All day – Buck a Shuck, drink specials.  Possibly the best HH deal in town!

Level – Small plates lounge make it especially good for Happy Hour – Mon-Fri, 5-630p $6 small plats $6-9 cocktails.

Tsunami – Mon-Fri – 430-600p 1/2 price sushi/ 1/2 price drafts, other daily specials. Great Asian fusion

Rams Head – especially good if you’re going to a show there – Mon-Fri, 3-7p, 1/2 price apps, $2 off drinks, 2.50 domestic beer, $3 drafts

Stan & Joe’s – Neighborhood spot – Mon- Fri 3-7p. Discounted drinks, daily food specials during HH. Buck a shuck Wed & Fri.

Metropolitan – $5 Mule, Grapefruit “frizz, $5 wine. Tu-Fri 4-7p. Only rooftop bar. Upscale/ hip vibe


Carroll’s Creek – 1/2 price appetizers in Bar / Lounge Monday through Thursday from 4 until close and Friday 4 – 7. Sundays 5-830 pm. Come enjoy your favorites at a fraction of the cost.  CC is one of our top recommendations for fine dining in town.  Great view!

Boatyard –  3 – 7 pm Monday through Friday (excluding holidays)….. $3 Draft Beer, House Wine and Well Drinks, $5 Bar Appetizers (huge amount of choices!) , 99c Oysters. See full menu here.  Specialty boat drinks (cocktails) all night, every night. Come and get your seat at the bar where local sailors, fishermen and lovers of the Chesapeake enjoy pint drinks, great crab cakes and the freshest local seafood.

Davis’ Pub – 3:30-6:30 pm Mon-Fri. Featured Triple D, locals place on back side of Eastport. Daily specials. Outdoor seating…

Chart House – Happy Hour – Sunday – Friday 4:30 pm – 7 pm. See full HH menu here.  Apps $4-5-6-7. $4.25 drafts, $6 & $8 wines, $5 spirits & $7 cocktails.  Come for the view

Driving Distance

Severn Inn – 3-6 pm Mon-Fri. $1 Oysters, grilled wings. $3-4 beer specials. Sweeping views across the Severn River to USNA.

The Point – 3-6 pm Mon-Fri – 1/2 price apps, $2 domestic drafts, $3.50 imports/craft, $5 wine. Live music 5-8 Wed/Thu. Waterside location brings in the locals & boaters, can get crowded.


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