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Best Historic Restaurants in Annapolis

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10 restaurants available nearby

A photo of Acqua al 2 - Annapolis restaurant
1. Acqua al 2 - Annapolis
4.8
Exceptional(798)
Price: Expensive
• Italian • Annapolis
Booked 40 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 Rams Head Tavern - Annapolis restaurant
2. Rams Head Tavern - Annapolis
4.3
Awesome(1678)
Price: Moderate
• American • Annapolis
Booked 21 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 Cafe Normandie restaurant
3. Cafe Normandie
4.6
Exceptional(2573)
Price: Moderate
• French • Annapolis
Booked 19 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(304)
Price: Moderate
• Gastro Pub • Annapolis
Booked 2 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 Iron Rooster restaurant
5. Iron Rooster
4.2
Awesome(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.
A photo of Blackwall Hitch - Annapolis restaurant
6. Blackwall Hitch - Annapolis
4.6
Exceptional(2474)
Price: Moderate
• American • Annapolis
Booked 30 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
7. Ruth's Chris Steak House - Annapolis
4.6
Exceptional(2842)
Price: Expensive
• Steakhouse • Annapolis
Booked 29 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
8. O'Brien's Oyster Bar & Seafood Tavern
4.7
Exceptional(434)
Price: Moderate
• Seafood • Annapolis
Booked 10 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
9. 18Twenty
4.6
Exceptional(172)
Price: Expensive
• Contemporary American • Stevensville
Booked 1 time today
Farm to table dishes, craft cocktails, and a cozy, upscale casual atmosphere.
A photo of Amalfi Coast Italian + Wine Bar restaurant
10. Amalfi Coast Italian + Wine Bar
4.7
Exceptional(936)
Price: Moderate
• Italian • Stevensville
Booked 12 times today
Benvenuti! Join us for traditional southern Italian food with a focus on dishes from the sun-splashed Amalfi Coast. Featuring an array of mouth-watering pasta, fresh seafood, char-grilled flatbread and more.

See what locals rave about

From verified diners like you
From verified diners like you
  • Christy
    Chicago / Illinois •1 review
    5.0
    Dined 3 days 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
  • Stephen
    Baltimore / Maryland •4 reviews
    5.0
    Dined 4 days ago
    Always a great experience. Predictable food, and another great show.
    More info
    Rams Head Tavern - AnnapolisPrice: Moderate• American• Annapolis
    •
    4.3
  • Philip
    Baltimore / Maryland •4 reviews
    4.0
    Dined 7 days ago
    The Amaroni was the worst I have ever tasted; I don't know why any restaurant would have this particular brand on their wine list.
    More info
    Acqua al 2 - AnnapolisPrice: Expensive• Italian• Annapolis
    •
    4.8
  • ben and carrie
    Tampa / Central Florida West •7 reviews
    5.0
    Dined on Nov 20, 2024
    I have been dining at Cafe Normandie since I was a midshipman (an early female) at the Naval Academy. I now live in Annapolis and this is one of my truly favorites. Do not miss the escargot !
    More info
    Cafe NormandiePrice: Moderate• French• Annapolis
    •
    4.6
  • Vicki
    San Francisco Bay Area •11 reviews
    5.0
    Dined on Oct 2, 2024
    Excellent reception, service and food. Old friends seeing each other after long absence. Restaurant was gracious giving us extended time to visit before and after eating. All four meals were delicious (crab cakes, chic sandwich, rockfish and watermelon salad). Accommodated special requirements of one diner for no alcohol (cooked or otherwise) with grace and generosity. We’d definitely go back when back in Annapolis.
    More info
    Iron RoosterPrice: Moderate• Breakfast• Annapolis
    •
    4.2

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