Flag House Inn

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Happy Hour in Annapolis – So Many Choices!

Design your own Happy Hour trail around downtown Annapolis

(Note – we have not updated this listing after start of pandemic – it’s very likely all bars and restaurants have stopped happy hour deals as they struggle to stay in business. Everyone in town now has outdoor dining, often in closed off streets… Market Space, Maryland Ave, upper Main, Inner West all close off on a rotating basis)

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 listen to guest feedback and adjust our list based on your own experiences.

But first – a word from our sponsors:

slice of vegetable quiche/pie, sausage slices, asparagus on a plate

Veggie quiche is one of our long standing and most popular breakfasts

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 – and it’s delicious – check out our Insta ).

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….

Thanks for listening – on with the list:


Fox’s Den – Weekdays 5:00-6:00pm: $4 off pizza/moules & frites; $3 off house cocktails; $2 off beers/wine/bourbon, $12 brick oven pizza Mondays, Wednesday wine special – Order bottle of wine get food item for free.  The pizzas are inventive, fresh and filling! (Our fave downtown)

Dock St. –  Sunday NFL specials…  other than that, Moe & Tommy & crew will take care of you! Great food, especially crab cakes…

Galway Bay –  Monday – Friday 330-630p – ~30% off apps, small plates, cocktails, beer & wine.  Wednesday – Irish Music Sessions in the Bar, Sunday – Brunch Menu 10:00-1:30, Entertainment Wed, Sat, Sun

Boatyard – HH is back at Boatyard Monday – Thursday 3-6p. Buck a shuck for oysters and drink specials!


Iron Rooster – Mon-Fri 8a – 10a (!) Bloodies, Mimosas, winne & RoosTarts (homemade Pop Tarts) +  & 3-6p House red/white $5, Orange crush $6, draft & apps 1/2 price.  You can easily make a meal of 2-3 apps/couple!

McGarvey’s – No happy hour but… buck a shuck for oysters all day.  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 Street

Sailor Oyster Bar (SOB) – Happy House Tuesday – Friday 4-530 pm, Saturday 12n-3p, Sunday All day – Buck a Shuck, drink specials.  Best variety of oysters 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

Stan & Joe’s – Neighborhood bar with fresh & local food! Mon-Fri all drinks & apps 1/2 price… Tuesday 1/2 price burgers, Sunnday $15 bottomless Bloodies & Mimosa + NFL game Day specials


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 Inn3-6 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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