Best Restaurants with a Happy Hour in Annapolis

Price

$$
$$$
$$$$

Cuisine

AmericanItalianSteakhouseSeafoodMexicanTapas / Small Plates

Regions

Baltimore SuburbsEastern ShoreGreater AnnapolisMaryland - DC Suburbs

Areas

AnnapolisDavidsonvillePasadenaSeverna ParkStevensville

Top Rated

CharmingFancyGood for business mealsGood for groupsGood for special occasionsGreat for fine wines

Dining Options

All dining options

Delivery only

Takeaway only

Seating Options

BarCounterStandardHigh TopOutdoor

Accessibility

Gender-neutral restroomWheelchair access

14 restaurants available nearby

A photo of Level Small Plates Lounge restaurant

1. Level Small Plates Lounge

4.5

Awesome(2257)

$$$$Price: Moderate

• American • Annapolis

Booked 3 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(1707)

$$$$Price: Moderate

• American • Annapolis

Booked 19 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

4.6

Exceptional(71)

$$$$Price: Moderate

• Italian • Annapolis

Booked 4 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

4.6

Exceptional(94)

$$$$Price: Expensive

• Contemporary American • Annapolis

Booked 3 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 Ruth's Chris Steak House - Annapolis restaurant

5. Ruth's Chris Steak House - Annapolis

4.5

Awesome(2890)

$$$$Price: Expensive

• Steakhouse • Annapolis

Booked 20 times today

Expect nothing less than an extraordinary meal and first-class service from one of the most outstanding prime steak houses in the world: Ruth's Chris Steak House. Among the most distinctive dining destinations in the area. At Ruth's Chris Steak House your service will always be first class-attentive but never fussy.

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

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

4.5

Awesome(7239)

$$$$Price: Moderate

• American • Annapolis

Booked 67 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

4.3

Awesome(454)

$$$$Price: Moderate

• Seafood • Annapolis

Booked 4 times today

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 True Food Kitchen - Annapolis restaurant

8. True Food Kitchen - Annapolis

4.5

Awesome(768)

$$$$Price: Moderate

• American • Annapolis

Booked 16 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.

A photo of Urbano - Annapolis restaurant

9. Urbano - Annapolis

3.8

Excellent(33)

$$$$Price: Moderate

• Mexican • Annapolis

Booked 2 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 Yellowfin Steak and Fish House restaurant

10. Yellowfin Steak and Fish House

4.5

Awesome(218)

$$$$Price: Moderate

• Seafood • Davidsonville

Booked 1 time today

Yellowfin features a bright, contemporary design, sunset views on the scenic South River, exceptional service and award-winning food. Voted Annapolis' Best Happy Hour 15 years in a row! Serving 7 species of fresh fish, hard carved steaks, pastas, full sushi menu and an assortment of fresh seafood entrees. Yellowfin also serves lunch and an All You Can Eat Sunday Brunch Buffet every Saturday and Sunday starting. Yellowfin specializes in serving parties of any size in our dining room and up to 200 in our lower level banquet facility. Our private, waterfront banquet facility is the perfect place for wedding receptions, business meetings, baby showers and class reunions. Yellowfin is one of Maryland's premier dinning destinations and famous for it's sunsets.

See what locals rave about

From verified diners like you

B
Bess
Baltimore / Maryland •2 reviews
4.0
Dined 3 days ago
Always a good place to go before the shows! Really appreciate the 10% discount.
More info
Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
•
4.3
G
GaryVIP
Baltimore / Maryland •1 review
5.0
Dined 4 days ago
Saturday night dinner in Annapolis. Noise was daunting but I managed to find a quiet spot with my date. We ordered scallops, burrata, and salad. The scallop portion was only three pieces, delicious but hardly shareable. Microplate would be more apt than small plate. The burrata was delicious, drizzled pesto and sun-dried tomatoes over crostini. The roasted beet salad plate was uneven. Walnuts were dropped onto a plate of smooth-leaf kale (not arugula). Overall, an adventurous menu. I will return to sample more of their offerings.
More info
Level Small Plates LoungePrice: Moderate• American• Annapolis
•
4.5
P
Paul
Washington, D.C. Area •1 review
5.0
Dined 6 days ago
Nicely decorated dining room, not too loud. The service was good, and we enjoyed the cobb salad and crab cake melt for reasonable prices. The double chocolate cake was outstanding.
More info
Red Red Wine BarPrice: Expensive• Contemporary American• Annapolis
•
4.6
N
NoelleVIP
Baltimore / Maryland •8 reviews
5.0
Dined on 5 Mar 2025
Wonderful as always. Great service and food! Always love our dinners there.
More info
Ruth's Chris Steak House - AnnapolisPrice: Expensive• Steakhouse• Annapolis
•
4.5
M
MarthaVIP
Baltimore / Maryland •38 reviews
5.0
Dined on 14 Feb 2025
Always love Harold Black ambience and cocktails (thank you ,Jordan, for the great skinny Cosmo ). Gabriel was an outstanding server - friendly , professional and fun .
More info
Harold Black - AnnapolisPrice: Moderate• Italian• Annapolis
•
4.6

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