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Best Fun Restaurants in Annapolis

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25 restaurants available nearby

A photo of Fox's Den restaurant
4.8
Exceptional(302)
Price: Moderate
• Gastro Pub • Annapolis
Booked 5 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 Level Small Plates Lounge restaurant
4.7
Exceptional(2225)
Price: Moderate
• American • Annapolis
Booked 15 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 Luna Blu - Annapolis restaurant
4.8
Exceptional(2413)
Price: Moderate
• Italian • Annapolis
Booked 14 times today
We opened in 2001 on the new up & coming hot spot of Inner West Street. We have grown into a neighborhood favorite among locals & tourists. Our cozy dining room with murals of the Amafi Coast is the perfect place for a date night or for making memories with friends & family. Offering innovative Italian fare prepared with a personal touch & the freshest local ingredients. All menu items are prepared fresh to order, this allows us to be very accommodating to food allergies. We have many options for vegans, pescatarians and gluten free diners.Wednesday & Saturday from May - Sept on West Street's 1st block we hold Dinner Under the Stars. All of the restaurants put tables & chairs under a light canopy, there is live music and dancing. We offer a 4 course special nightly, 1/2 priced bottle of we every Wednesday, Pizza & Wine pairing Tuesday & Thursday nights & bi weelky wine dinners.View our events & specials www.lunabluofannapolis.com Thanks for supporting local business!
A photo of Harold Black - Annapolis restaurant
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.
A photo of Rams Head Tavern - Annapolis restaurant
4.3
Awesome(1675)
Price: Moderate
• American • Annapolis
Booked 12 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 Red Red Wine Bar restaurant
3.8
Excellent(78)
Price: Expensive
• Contemporary American • Annapolis
Booked 9 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 Chart House Prime - Annapolis restaurant
4.6
Exceptional(7024)
Price: Expensive
• Seafood • Annapolis
Booked 75 times today
Original Hospitality. Creative Culinary. Modern Energy.Experience the evolution of dining with Chart House Prime - where sophistication meets trendsetting cuisine. Our approachable yet professional service, coupled with the finest ingredients, brings you the best in refined seafood and steakhouse cuisine with a unique fusion of elegance and vibrance, creating a truly remarkable experience.
A photo of Agave Mexican Restaurant & Tequila Bar - Annapolis restaurant
4.3
Awesome(127)
Price: Expensive
• Mexican • Annapolis
Booked 18 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 Carpaccio Tuscan Kitchen restaurant
4.6
Exceptional(2313)
Price: Moderate
• Italian • Annapolis
Booked 38 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 Iron Rooster restaurant
4.1
Excellent(1011)
Price: Moderate
• Breakfast • Annapolis
Booked 5 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.

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See what locals rave about

From verified diners like you
From verified diners like you
  • 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!
    More info
    Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
    4.3
  • TMC3vip
    Virginia •11 reviews
    5.0
    Dined 6 days ago
    Service is excellent and attentive, the atmosphere is closer to NYC Manhattan than Annapolis which I love, cozy yet comfortable. Alternatively sit outside and you feel like you are in Europe! Excellent cocktails and bread service before dinner. The 4 course special includes an appetizer, a salad, an entree, and a dessert, a terrific value even if you need to take the dessert home with you after such a wonderful Italian meal. The quality and taste of the food is Luna Blu’s strongest suit, creative dishes and presentations that will leave you eagerly awaiting a return visit. Best Italian in Naptown by far!
    More info
    Luna Blu - AnnapolisPrice: Moderate• Italian• Annapolis
    4.8
  • 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.
    More info
    Harold Black - AnnapolisPrice: Moderate• Italian• Annapolis
    4.2
  • 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.
    More info
    Level Small Plates LoungePrice: Moderate• American• Annapolis
    4.7
  • Matthew
    Washington, D.C. Area •7 reviews
    4.0
    Dined on Nov 1, 2024
    Food and drinks fantastic! Way too loud to have a conversation.
    More info
    Fox's DenPrice: Moderate• Gastro Pub• Annapolis
    4.8

Discover best fun restaurants in Annapolis

Discover the vibrant dining scene in Baltimore, Maryland, and Greater Anapolis, where "fun" is the keyword in every gastronomic adventure! This region thrives with a variety of restaurants that promise not just meals but memorable experiences. From interactive dining setups that engage all your senses to lively atmospheres perfect for both lively group outings and cozy, playful dates, each establishment brings its own unique flair to the table. Culinary creativity is at the forefront, with menus featuring everything from gourmet twists on comfort food to innovative dishes that cater to health-conscious diners. The dining scene here is characterized by a blend of casual sophistication and inviting charm, making it a top choice for anyone looking to combine great food with great times. Whether you're a local or a visitor, these restaurants in Baltimore and Greater Annapolis offer the perfect backdrop for enjoying life and delicious cuisines. Expect top-notch service, a warm ambiance, and a dining experience that will make you want to return time and again.

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