Best Casual Restaurants in Annapolis

27 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 12 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(1676)

Price: Moderate

• American • Annapolis

Booked 18 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.

3. Fox's Den

4.7

Exceptional(304)

Price: Moderate

• Gastro Pub • Annapolis

Booked 1 time today

An american craft Gastropub concentrating on local and small batch beers, whiskey, spirits and hand crafted cocktails along with a brick oven menu with Wood Fired Pizza, shareable items, and small plates. *Please note for online wait listed reservations do have a 5-10 min time frame to arrive for your reservation to be sat*

A photo of Harold Black - Annapolis restaurant

4. Harold Black - Annapolis

4.2

Awesome(66)

Price: Moderate

• Italian • Annapolis

Booked 12 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.

5. Red Red Wine Bar

3.8

Excellent(79)

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 Trophy Room - Annapolis restaurant

6. Trophy Room - Annapolis

3.5

Very Good(0)

Price: Moderate

• American • Annapolis

Booked 1 time today

Coming Soon!

A photo of Carpaccio Tuscan Kitchen restaurant

7. Carpaccio Tuscan Kitchen

4.6

Exceptional(2319)

Price: Moderate

• Italian • Annapolis

Booked 13 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.

8. Seasalt Annapolis

new

4.3

Awesome(8)

Price: Expensive

• Seafood • Annapolis

Booked 25 times today

SEASALT is an ingredient driven seafood restaurant and raw bar located in the States Capital. We source fresh, seasonal, and sustainable fish, shellfish, meats, and produce. We thoughtfully and creatively make seafood dishes that have amazing global flavors. The SEASALT bar is a comfortable and friendly gathering place that serves award winning cocktails, curated spirits, wines, and beers. We like to say that we deliver all of this with true Irish hospitality and Southern charm.

9. Iron Rooster

4.2

Awesome(1011)

Price: Moderate

• Breakfast • Annapolis

Booked 4 times today

Whether you're looking for breakfast all day, lunch, supper or drinks, at Iron Rooster you'll find a new twist on traditional comfort food, legendary hospitality, and a real sense of community. Join us every day for breakfast, lunch, supper and late-night drinks. Whenever you're here, you'll enjoy delicious food, a cold drink, and an extra helping of hospitality.

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

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

4.4

Awesome(7062)

Price: Moderate

• American • Annapolis

Booked 88 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.

See what locals rave about

From verified diners like you

C
Christy
Chicago / Illinois •1 review
5.0
Dined 1 day ago
We arrived 20 min early and our table was ready and we were seated immediately! Food and service were amazing and timely! This is our fav spot and it was fun to bring family there. Always SO good!
More info
Fox's DenPrice: Moderate• Gastro Pub• Annapolis
•
4.7
S
Stephen
Baltimore / Maryland •4 reviews
5.0
Dined 2 days ago
Always a great experience. Predictable food, and another great show.
More info
Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
•
4.3
L
L
Los Angeles •4 reviews
4.0
Dined on Nov 18, 2024
We had a mix of flights, glasses of wines, mixed cocktails and light bites. Lots of fun, unique interior, good value and great staff!
More info
Red Red Wine BarPrice: Expensive• Contemporary American• Annapolis
•
3.8
C
Cory
Washington, D.C. Area •7 reviews
5.0
Dined on Nov 17, 2024
We had a great experience. The server gave me the wrong drink. When I pointed it out, she corrected the error quickly.
More info
Harold Black - AnnapolisPrice: Moderate• Italian• Annapolis
•
4.2
T
TOSHKAvip
Baltimore / Maryland •14 reviews
5.0
Dined on Nov 16, 2024
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.
More info
Level Small Plates LoungePrice: Moderate• American• Annapolis
•
4.7

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Annapolis

Best Casual Restaurants in Annapolis

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27 restaurants available nearby

1. Level Small Plates Lounge

2. Rams Head Tavern - Annapolis

3. Fox's Den

4. Harold Black - Annapolis

5. Red Red Wine Bar

6. Trophy Room - Annapolis

7. Carpaccio Tuscan Kitchen

8. Seasalt Annapolis

9. Iron Rooster

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

See what locals rave about

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