Best Restaurants with a Happy Hour in Annapolis

16 restaurants available nearby

A photo of Level Small Plates Lounge restaurant

1. Level Small Plates Lounge

4.7

Exceptional(2225)

Price: Moderate

• American • Annapolis

Booked 14 times today

Level was established as a locals first atmosphere with welcoming attitudes to all. Our cocktails are all handcrafted with fresh juices, mixes, and garnishes. One of the many things that makes us unique is our ability and commitment to source as many fresh ingredients locally from the State of Maryland and surrounding markets. We are dedicated to supporting the area small businesses, watermen, farmers, and the environment on a local and global level. Our small plates style of dining encourages this sense of community and sharing. Level is located on the second block of West Street known as the Arts District.

A photo of Rams Head Tavern - Annapolis restaurant

2. Rams Head Tavern - Annapolis

4.3

Awesome(1675)

Price: Moderate

• American • Annapolis

Booked 17 times today

For over 30 years, Rams Head has been an award-winning favorite serving creative tavern fare. Rams Head offers an outstanding happy hour, a legendary beer selection, and extraordinary live music 7 nights a week. Whether in one of the cozy dining rooms, the historic pub, or on the Wisteria-covered patio, you'll see why so many Annapolitans consider Rams Head their second home. .We do not accept reservations for outdoor dining. Have tickets to a show at Rams Head On Stage? If taking advantage of our FREE Premium On Stage Experience, please make note in the 'special request' section while making your reservation.

A photo of Harold Black - Annapolis restaurant

3. Harold Black - Annapolis

4.2

Awesome(66)

Price: Moderate

• Italian • Annapolis

Booked 13 times today

Harold Black is a warm, intimate bar that is quiet enough to hear your conversation yet lively enough to keep you talking. A list of house cocktails gives you a range of options, additionally, the bartenders are ready to work their magic if you have something else in mind. Harold Black serves a light-fare menu with a selection of cured meats, cheeses and desserts. Please be aware of a few house rules: 1. We look forward to having you join us and are happy to hold your table for up to fifteen minutes. 2. Your booking reserves your seats for 2 hours. 3. Due to our small size we cannot guarantee booth seating. 4. Our maximum party size is six people, no exceptions, and unfortunately we cannot book multiple tables for one group. 5. Given that Harlod Black is a cocktail bar, the age requirement for entering is 21. To buy out Harold Black for a private event or book our private dining room, please email events@haroldblack.com.

4. Red Red Wine Bar

3.8

Excellent(78)

Price: Expensive

• Contemporary American • Annapolis

Booked 8 times today

Casual contemporary American made-from-scratch cuisine focused on seasonal entrées, house-made pizzas, cheese and charcuterie boards. Extensive wines by the glass program with something for everyone including local, craft beer and seasonal craft cocktails. A cozy, Bohemian haunt where you and your crew can get away from it all or enjoy one of the biggest outdoor dining patios in downtown Annapolis.

A photo of Carpaccio Tuscan Kitchen restaurant

5. Carpaccio Tuscan Kitchen

4.6

Exceptional(2313)

Price: Moderate

• Italian • Annapolis

Booked 40 times today

Comfortable, yet Sophisticated. CARPACCIO offers more than just a menu of authentic Italian specialties. Revel in our uptown ambiance indoors or out while you savor the perfectly portioned and exquisitely flavored pastas, pizzas, meats and seafood dishes. Experience downtown Annapolis on our fountain view patio and comfortably enjoy observing the passersby. Whether you’re meeting a friend for an appetizer and glass of wine or celebrating a family or corporate event, Carpaccio Tuscan Kitchen & Wine Bar combines flavour, service, authenticity, ambiance & style to bring you all the best that Italy has to offer.

A photo of Cooper's Hawk Winery & Restaurant - Annapolis, MD restaurant

6. Cooper's Hawk Winery & Restaurant - Annapolis, MD

4.4

Awesome(7053)

Price: Moderate

• American • Annapolis

Booked 134 times today

Experience the perfect fusion of award-winning wines, Napa-style tasting rooms, and modern casual dining at Cooper's Hawk Winery & Restaurants. Enjoy contemporary American cuisine influenced by international flavors from our scratch kitchen. Each dish is expertly paired with our selection of wines for the best food and wine match. Whether you explore the tasting room for a pre- or post-dinner adventure or join the world's largest wine club, we believe in the power of food and wine to create lasting connections. Dining reservations are highly recommended, but walk-in guests are always welcome on a first-come, first-serve basis. Gluten-free and vegetarian dishes are available.

A photo of O'Brien's Oyster Bar & Seafood Tavern restaurant

7. O'Brien's Oyster Bar & Seafood Tavern

4.6

Exceptional(432)

Price: Moderate

• Seafood • Annapolis

Booked 8 times today

O’Brien’s Oyster Bar and Seafood Tavern is an Annapolis institution. We take pride in offering honest local Chesapeake cuisine in a comfortable setting. Our bar is legendary and well known in the boating and Naval Academy community. Our full menu is available until 10pm and we offer a late pub menu till closing. Check our calendar for after dinner music and entertainment.

A photo of Agave Mexican Restaurant & Tequila Bar - Annapolis restaurant

8. Agave Mexican Restaurant & Tequila Bar - Annapolis

4.3

Awesome(127)

Price: Expensive

• Mexican • Annapolis

Booked 21 times today

RESERVATIONS: We are accepting dining reservations 30 days out, simply meaning today's date plus 30 days.CANCELLATION POLICY: If you cancel or no show within 12 hours of your reservation, your credit card will be charged $25/per person. (This includes updating guest count)All proceeds go towards the kitchen’s continued culinary education, research, and development.YOUNG GUESTS: We do not offer child seating (high chairs/booster seats) of any kind, nor a children’s menu, and we are unable to accommodate strollers in the dining room.Please feel free to bring your own portable dining chair(s) for your little one(s).PATIO: Our patio is located outside, along Annapolis Street, in West Annapolis.Most of our patio tables are in full sun, with a limited amount of tables in the shade.You may request a patio table, however it is not guaranteed. Please take note if you are uncomfortable with sun exposure and outdoor elements. Heaters are not provided in the fall through spring.

A photo of Urbano - Annapolis restaurant

9. Urbano - Annapolis

3.3

Good(23)

Price: Moderate

• Mexican • Annapolis

Booked 11 times today

Are you ready to embark on a flavor -packed journey through the heart of Mexico, right here in Annapolis Town Center? Urbano Tex Mex invites you to experience the vibrant colors, bold spices, and authentic tastes of Tex- Mex cuisine like never before.At Urbano Tex Mex, we are passionate about bringing together the best of Texan and Mexican culinary traditions. Our chefs blend premium ingredients with time-honored recipes to create mouthwatering dishes that will tantalize your taste buds.

A photo of True Food Kitchen - Annapolis restaurant

10. True Food Kitchen - Annapolis

4.4

Awesome(732)

Price: Moderate

• American • Annapolis

Booked 26 times today

True Food Kitchen is a chef-driven restaurant and scratch bar that was founded by Dr. Andrew Weil, the pioneer of integrative medicine, to provide food that tastes great and is good for you. Our menu features food and drinks crafted with nutrient-dense ingredients and carefully sourced proteins from the world’s most responsible and sustainable growers, farmers and producers. Expand your palate with our Edamame Dumplings, grab a bite of comfort food with our Grass-fed Burger or Lasagna Bolognese, or enjoy lighter fare with our O.G. Tuscan Kale Salad with Grilled Sustainable Salmon. Regardless of the occasion, we know our Annapolis guests leave feeling energized, satisfied and most importantly, feeling great. Located in Annapolis at Annapolis Town Center, at the corner of Harker Place and Town Centre Boulevard, across the street from Target. New flavors, new combinations, new obsessions. Come see us for something completely new and delicious.

See what locals rave about

From verified diners like you

J
jennvip
Baltimore / Maryland •2 reviews
5.0
Dined 1 day ago
Fantastic place in every way! Our favorite restaurant! A must try.
More info
Carpaccio Tuscan KitchenPrice: Moderate• Italian• Annapolis
•
4.6
S
Suzanne
Baltimore / Maryland •3 reviews
5.0
Dined 4 days ago
Ate dinner at the Rams Head Tavern prior to a show at the Rams Head On Stage. The dinner was not fancy or elegant, but it was perfect for a pre-show meal. I didn't feel stuffed, or uncomfortably full. There was a 10% discount since it was a pre-show reservation, and if you use Gotts Garage a QR code is provided for a discount on parking fees. AND, as a long-time Annapolitan and semi-frequent customer, I do believe the Rams Head Tavern has lowered their dinner prices post pandemic!
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Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
•
4.3
C
Cory
Washington, D.C. Area •7 reviews
5.0
Dined 6 days ago
We had a great experience. The server gave me the wrong drink. When I pointed it out, she corrected the error quickly.
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Harold Black - AnnapolisPrice: Moderate• Italian• Annapolis
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4.2
T
TOSHKAvip
Baltimore / Maryland •14 reviews
5.0
Dined 7 days ago
What an excellent experience! The service was top notch, food was tasty and hot, and the ambiance was fun and pretty. My husband I ordered the crab lettuce wraps, lamb chops, beef kabobs, grilled oysters and tuna tartare… we’d give everything 5 stars. The only item we didn’t love was the crab bruschetta due to the amount of mayo but the bruschetta bread was soft and delicious and crab was fresh and abundant. We’ll definitely come back to this restaurant.
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Level Small Plates LoungePrice: Moderate• American• Annapolis
•
4.7
KZ
KathyZ
Baltimore / Maryland •6 reviews
5.0
Dined on Nov 7, 2024
It is such a lovely space, the food was delicious, the wine flights were creative and tasty. Even our Manhattan was superb. Really enjoyed our evening there and look forward to going again.
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Red Red Wine BarPrice: Expensive• Contemporary American• Annapolis
•
3.8

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Annapolis

Best Restaurants with a Happy Hour in Annapolis

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16 restaurants available nearby

1. Level Small Plates Lounge

2. Rams Head Tavern - Annapolis

3. Harold Black - Annapolis

4. Red Red Wine Bar

5. Carpaccio Tuscan Kitchen

6. Cooper's Hawk Winery & Restaurant - Annapolis, MD

7. O'Brien's Oyster Bar & Seafood Tavern

8. Agave Mexican Restaurant & Tequila Bar - Annapolis

9. Urbano - Annapolis

10. True Food Kitchen - Annapolis

See what locals rave about

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