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We celebrate Happy Hour because it is a time to meet up with friends after a long day at work. During Happy Hour, you can start to unwind and shed the stresses of the day. Happy Hour can also mark the beginning of the weekend. We visited restaurants in the Annapolis area that offer Happy Hour specials and developed a list of our top places. They are numbered but unranked. As restaurants often change their menus, you may want to call ahead to verify Happy Hour specials. We also note those establishments that do not offer Happy Hour pricing at their outside dining areas.
$5 Wines, Beers, single liquor drinks. $8 signature appetizers. Tucked in between Middleton’s Tavern and historic Shiplap House, this tavern has been a favorite spot for locals for over 40 years, with possibly the best cheeseburgers, oysters and crab balls in town. Sit at the gleaming bar and have an oyster-shooter while absorbing the flavors of working Annapolis.
Happy Hour: Mon–Fri, 2:00–6:00 PM | mcgarveysannapolis.com | 8 Market Space, Annapolis, MD 21401
Food specials include $1 oysters, grilled sweet chili wings and more. Beer specials: Abita $3.95 and Natty Boh $2.95. Wine Specials: Select wines $6.95/glass. Dazzle the senses while absorbing fresh oysters and sweeping views through an elegant wall of windows. You almost feel as if you were dining outside. Alert: Happy Hour excludes outdoor bar.
Happy Hour: Mon–Fri, 3:00–6:00 PM | severninn.com | 1993 Baltimore Annapolis Blvd, Annapolis, MD 21409
For a heady dose of Ego Alley, you will sit closer to the water than anywhere else in Annapolis. Watch boats wander by or wiz along while sampling appetizers, and craft and domestic beers at reduced prices. There are many tourists so be prepared. Alert: Happy Hour excludes waterside bar.
Happy Hour: Mon–Fri, 4:00–7:00 PM | pussersannapolis.com | 80 Compromise Street, Annapolis, MD 21401
1/2 priced appetizers, $2 Domestic drafts, $3.50 craft/import drafts, $1 off rail drinks, $5 house wines, at inside and outside seating. Live Music every Wed/Thurs from 5:00–8:00 PM. Wine O-Wednesday’s: 1/2 price bottles of House Wine. This is a truly water-side experience. Arrive by boat or car, and enjoy live music, fresh seafood and their famous Nutty Buddies that hark back to an earlier era. Boaters and locals alike love this place so the wait may be very long.
Happy Hour: Mon–Fri, 3:00–6:00 PM | thepointcrabhouse.com | 700 Mill Creek Road, Arnold, MD 21012
Beer & Wine specials, $1 local oysters. If you want to try a unique menu and a variety of fresh oysters with your mates, this is your place. Located on West Street, this locally-owned watering hole may be tiny but overflows with character, characters and tasty small plates paired thoughtfully with craft beers and wines.
Happy Hour: Tues–Fri, 4:00–5:30 PM, Sat 12:00–3:00 PM, Sun, 12:00–Close | sailoroysterbar.com | 196 West Street, Annapolis, MD 21401
Select domestic/imported bottles, select rail cocktails, select wines by the glass. Daily specials and $1 oysters. With its low-key Eastport tempo, the Hitch is nautical plush with a coastal menu. Beware: the appetizers during Happy Hour, especially the calamari and seared tuna, are addicting. Alert: The Rooftop does not offer Happy Hour pricing.
Happy Hour: Mon–Fri, 3:00–7:00 PM | theblackwallhitch.com | 400 Sixth Street, Annapolis, MD 21403
$5 crab dip, $5 red or white wine of the day, $5 sangria, $3 draft beer of the day, $5 well drinks. 35+ wines by the glass and 120+ wines by the bottle. The food here is a fusion of Maryland coastal and Cali flare. If you are seeking an elegant velvet cafe, you have found it. Relax in an Edith Wharton-inspired space, with curvaceous settees and cozy booths, while sampling flights of wine.
Happy Hour: Mon–Fri, 3:00–6:00 PM | redredwinebar.com/annapolis | 189B Main Street, Annapolis, MD 21401
$5 Kentucky Mule, $5 grapefruit or pineapple frizz, select $5 wines and specially priced appetizers. Happy Hour is on Tuesdays, Wednesdays and Fridays 4-7pm at this hip and happy, locally-owned, West Street establishment. Admire its art-rouge décor and enjoy both on the roof and downstairs-select drinks and food.
Happy Hour: Tues–Fri, 4:00–7:00 PM | metropolitanannapolis.com | 175 West Street, Annapolis, MD 21401
Beer, wine and drink specials!
Located far from the bustling crowd in Eastport, this unpretentious pub built in the 1930s exudes the laisse faire style of Old Eastport and marina life. It offers outstanding steamed shrimp served up with Chesapeake pride and a hearty dose of attitude.
Happy Hour: Mon–Fri, 3:30–6:30 PM | davispub.com/menu | 400 Chester Avenue, Annapolis, MD 21403
Located in the historic heart of Annapolis right off of Church Circle, the sassy Den offers $3 off house cocktails, $2 off beers/wines by the glass and $4 off pizza/mussels & frites. It is an old-fashioned pub, serving up local and small-batch beers and spirits along with a brick oven menu with flatbreads and mussels.
Happy Hour: Mon–Fri, 5:00–6:00 PM | foxsden.com | 179B Main Street, Annapolis, MD 21401
Annapolis Home Magazine 2019