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Best Historic Restaurants in Annapolis

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11 restaurants available nearby

A photo of Rams Head Tavern - Annapolis restaurant
1. Rams Head Tavern - Annapolis
4.2
Awesome(1688)
Price: Moderate
• American • Annapolis
Booked 22 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 Acqua al 2 - Annapolis restaurant
2. Acqua al 2 - Annapolis
4.7
Exceptional(824)
Price: Expensive
• Italian • Annapolis
Booked 53 times today
Located in the heart of Annapolis, Acqua al 2 offers an authentic Tuscan dining experience. Featuring a wide array of vegetarian pasta, hand-carved steaks, and fresh seafood, as well as an extensive Italian wine list, Acqua is perfect for a celebratory dinner, an intimate date night, or a low key get-together with friends.
A photo of Cafe Normandie restaurant
3. Cafe Normandie
4.5
Awesome(2588)
Price: Moderate
• French • Annapolis
Booked 26 times today
Consistently voted "Most Romantic" restaurant, Cafe Normandie combines French cuisine with local Maryland specialities. A family business, we have been located in Historic Annapolis for 35 years.
A photo of Fox's Den restaurant
4. Fox's Den
4.7
Exceptional(307)
Price: Moderate
• Gastro Pub • Annapolis
Booked 13 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 The Choptank - Annapolis restaurant
5. The Choptank - Annapolis
4.6
Exceptional(1455)
Price: Expensive
• Seafood • Annapolis
Booked 107 times today
Local Chesapeake Seafood and Crabhouse featuring live entertainment, craft cocktails, carefully curated wine list, and the best scenic view of the Chesapeake in the region!
A photo of Iron Rooster restaurant
6. Iron Rooster
4.4
Awesome(1014)
Price: Moderate
• Breakfast • Annapolis
Booked 11 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 Blackwall Hitch - Annapolis restaurant
7. Blackwall Hitch - Annapolis
4.5
Awesome(2484)
Price: Moderate
• American • Annapolis
Booked 25 times today
We can't wait for you to dine with us at Blackwall Hitch Annapolis! A dining experience blending the area’s finest in tastes & talents, Blackwall Hitch is a coastally inspired concept that creates a local connection. Here you’ll find seasonally driven and locally sourced food and spirits, great local music and the area’s friendliest staff and patrons. With each visit as you take in the local flavor, we guarantee you’ll be hooked in no time. Get hooked on the flavor.
A photo of Ruth's Chris Steak House - Annapolis restaurant
8. Ruth's Chris Steak House - Annapolis
4.6
Exceptional(2858)
Price: Expensive
• Steakhouse • Annapolis
Booked 54 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 O'Brien's Oyster Bar & Seafood Tavern restaurant
9. O'Brien's Oyster Bar & Seafood Tavern
4.6
Exceptional(440)
Price: Moderate
• Seafood • Annapolis
Booked 16 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 18Twenty restaurant
10. 18Twenty
4.6
Exceptional(173)
Price: Expensive
• Contemporary American • Stevensville
Booked 7 times today
Farm to table dishes, craft cocktails, and a cozy, upscale casual atmosphere.

See what locals rave about

From verified diners like you
From verified diners like you
  • Michael
    Washington, D.C. Area •2 reviews
    5.0
    Dined 2 days ago
    The staff was wonderful on Christmas Eve! Our server Julia was awesome and super accommodating. Elsa, the manager was very sweet and sent my wife an amazing dessert for her Birthday. We had a great time and the views from the upper level at Christmas were beautiful. There were some rowdy Christmas revealers at the bar but Elsa quieted them down. 😎 I highly recommend the restaurant for any occasion. We had a party of seven and everyone left very happy and satisfied.
    More info
    The Choptank - AnnapolisPrice: Expensive• Seafood• Annapolis
    •
    4.6
  • IleneVIP
    London •198 reviews
    5.0
    Dined 2 days ago
    The tuna tartar was wonderful and the filet mignon with blueberry sauce was exception. We had the Italian cheese cake for dessert and it was delicious.
    More info
    Acqua al 2 - AnnapolisPrice: Expensive• Italian• Annapolis
    •
    4.7
  • AnitaVIP
    Washington, D.C. Area •2 reviews
    5.0
    Dined 5 days ago
    Cool vibe! Started in the stage, then down to the tavern bar, and then upstairs to dinner. Where else can you listen to music, historic bar !and them a tasteful dining room? Wonderful server, attentive in just the right way.
    More info
    Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
    •
    4.2
  • Margaret
    Washington, D.C. Area •12 reviews
    4.0
    Dined on 19 Dec 2024
    I absolutely love Cafe Normandie, it never disappoints. Today I took a friend for a birthday lunch, and it was lovely. For this visit, I rated it a 4 rather than a 5 because the escargot, while delicious, were short—out of a dozen, four had inaccessible fillings.
    More info
    Cafe NormandiePrice: Moderate• French• Annapolis
    •
    4.5
  • jeanne
    Baltimore / Maryland •1 review
    5.0
    Dined on 15 Dec 2024
    Alex was amazing! We got to briefly chat with Sam too. The communal feel from the servers always makes the experience so much better. We had the Marissa, Vincent, and Mediterranean salad. I’d repeat that exact order
    More info
    Fox's DenPrice: Moderate• Gastro Pub• Annapolis
    •
    4.7

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