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Best Casual Restaurants in Annapolis

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27 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 7 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
4.4
Awesome(1708)
Price: Moderate
• American • Annapolis
Booked 16 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 Fox's Den restaurant
3. Fox's Den
4.7
Exceptional(318)
Price: Moderate
• Gastro Pub • Annapolis
Booked 7 times 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
4.6
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.
A photo of Red Red Wine Bar restaurant
5. Red Red Wine Bar
4.6
Exceptional(94)
Price: Expensive
• Contemporary American • Annapolis
Booked 2 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
4.0
Excellent(0)
Price: Moderate
• American • Annapolis
Coming Soon!
A photo of Seasalt Annapolis restaurant
7. Seasalt Annapolis
4.6
Exceptional(98)
Price: Expensive
• Seafood • Annapolis
Booked 27 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.
A photo of Carpaccio Tuscan Kitchen restaurant
8. Carpaccio Tuscan Kitchen
4.6
Exceptional(2357)
Price: Moderate
• Italian • Annapolis
Booked 23 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
9. Cooper's Hawk Winery & Restaurant - Annapolis, MD
4.5
Awesome(7239)
Price: Moderate
• American • Annapolis
Booked 72 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 Iron Rooster restaurant
10. Iron Rooster
4.5
Awesome(1009)
Price: Moderate
• Breakfast • Annapolis
Booked 3 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.

See what locals rave about

From verified diners like you
From verified diners like you
  • OpenTable Diner
    Baltimore / Maryland •2 reviews
    5.0
    Dined 1 day ago
    Excellent experience from start to finish! Great service at dinner, then saw Lachy Doley on stage and everything was fabulous in the venue. Definitely our favorite place in Annapolis!!!!
    More info
    Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
    •
    4.4
  • GaryVIP
    Baltimore / Maryland •1 review
    5.0
    Dined 5 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
  • OpenTable Diner
    Baltimore / Maryland •2 reviews
    5.0
    Dined 6 days ago
    Lots of fun and many different pizzas. The duck fat fries and Brussels sprouts are excellent!
    More info
    Fox's DenPrice: Moderate• Gastro Pub• Annapolis
    •
    4.7
  • Paul
    Washington, D.C. Area •1 review
    5.0
    Dined 7 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
  • 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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