White yachts floating in harbor at sunset

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 a few 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 our own experiences.


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

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, Wed wine – Order bottle of wine get food item for free

Dock St. –  Happy Hour every day 4-7pm , Monday $7 Burger/$5 Wings (1/2 price), Tuesday $3 off crab cake (Top 5 crab cake in town)

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.  Great setting

Iron Rooster – Mon-Fri 3-7p House red/white $5, Iron crush $5, draft of the day $5, 1/2 price apps

West St

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


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, 99c Oysters.  Specialty 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. Ease into the evening and enjoy the Boatyard’s new Happy Hour.

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

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