The Best Restaurants In Annapolis, Maryland

Family-owned and operated since 1965, Chick and Ruth’s Delly is a local dining landmark. Located in the heart of historic downtown Annapolis, the cozy, kitsch deli is known for its delicious diner food. The menu features everything from breakfast fare, pizzas, burgers and its legendary piled-high sandwiches. Particularly hungry guests may want to take on Chick & Ruth’s Man vs. Food Challenge where consuming a six-pound milkshake and a colossal one-and-a-half-pound burger or sandwich within one hour wins daring diners a t-shirt. But if you try just one thing, make sure it’s Chick & Ruth’s jumbo lump crab cakes as they’re often hailed as the best in Maryland.

A must-try dining destination for fans of fine food and history is Reynolds Tavern. Its not only the oldest tavern in Annapolis but also one of the oldest in the country and a fine example of local Georgian architecture. A traditional English afternoon tea is served in the tavern’s restaurant. This is followed by a dinner menu of contemporary American plates like the shrimp and grit appetizer with bacon tomato jam and tasso ham gravy and the Chesapeake crab cake entrée with succotash and mash potato. Head downstairs to the 1747 Pub, located in the tavern’s cozy cellar, for casual fare like bangers and mash or a burger served up alongside craft brews.

One of the area’s most lauded restaurants, Osteria 177 was founded by Verona-raised owner and chef Arturo Ottaviano in 2006. Since then it has welcomed a steady stream of guests who leave raving about the restaurant’s authentic northern Italian fare. Elegant appetizers like beef carpaccio with arugula, parmesan and capers are combined with exquisite entrées such as duck breast with fresh blueberries in port wine sauce or homemade gnocchi with gorgonzola cheese sauce. All can be perfectly paired with one of Osteria 177’s carefully selected range of Italian wines. Its interior is just as elegant as its menu, a chic art deco space complemented by modern art and stylish chandeliers.

With its lovely location on the shores of Spa Creek, it’s not surprising that Carrol’s Creek was voted the city’s favorite waterfront restaurant in What’s Up? Magazine’s 2015 Best of Annapolis Award. Its charming locale isn’t the only thing that’s garnered its loyal following since the restaurant first opened over 30 years ago. Seafood and steaks are Carrol’s Creek’s specialty, and guests will find local favorites like Maryland cream of crab soup. For entrées, try the almond-crusted mahi mahi with sugar snap peas and tropical fruit salsa or grilled filet mignon with caramelized sweet onions, wild mushroom sauté, scalloped potatoes and a cabernet glace de viande.

Located in a beautifully converted bungalow in Annapolis’ charming Eastport neighborhood, Vin 909 has been delighting local diners with its seasonal, farm-to-table fare and stunning wine selection since 2011. While owner Alex Manfredonia and Executive Chef Justin Moore describe Vin 909’s menu as American, there’s a hint of other cultures in dishes like pan-fried rockfish with egg noodles and green chili curry broth. Try the restaurant’s much-loved brick oven pizzas especially the ‘spotted pig’ topped with spicy soppressata, wild boar meatballs, mozzarella, basil and provolone. Vin 909’s wine list is carefully curated with offerings from Europe and America. Guests can enjoy a few craft beers too.

For a laid-back evening of great beers and delicious seafood, local diners in the know head straight for Boatyard Bar & Grill. This Eastport dining destination was opened by Dick Franyo in 2001. Inside, the restaurant is a tribute to all things Chesapeake Bay with plenty of wood, nautical colors and maritime memorabilia. This sets the scene for dishes like spicy Maryland crab soup with beef broth, bacon and lump blue crab meat and the Boatyard’s specialty beer-battered cod served with crispy French fries and homemade tartar sauce. Regular live music and annual events like Boatyard’s charity Beach Bash offer regular entertainment.

Owners Gonzalo Fernandez, a native of Asturias, and Oaxaca-born Alberto Serrano came together in 1999 to open Jalapeños. The restaurant’s raved about cuisine is a perfect combination of the Spanish and Mexican heritages. Alberto’s brother Chef Obed Serrano heads up Jalapeños’ kitchen, cooking a wide range of tapas and antojitos, like Spanish-style chicken meatballs with brandy cream sauce or Oaxaca-style guacamole. There’s also bigger plates like traditional Mexican mole with chicken and the salmon a la Navarra, which is a filet of salmon sautéed with Serrano ham, capers and white wine. Jalapeños’ drinks are just as authentic as its eats with plenty of Spanish and Mexican beers, tequila and sangria on offer.

Founded in 2015 by Culinary Institute of America graduates Jeremy and Michelle Hoffman, Preserve is a casual and contemporary American restaurant with a focus on seasonal produce. Its concise, but tempting menu features creative dishes like pan-roasted Rhode Island fluke with chow-chow and cauliflower puree and gnocchi with kimchi, oyster mushrooms and crispy onions. Weekend brunch offers fare like fried egg grits with roasted vegetables and pea shoots or cinnamon chip French toast with whipped cream and maple syrup served alongside mimosas and bloody marys.

Voted Annapolis’ best seafood restaurant countless times since its first opened back in the 1980s, O’Leary’s is a pescatarian’s paradise. Located in a beautiful, bright blue bungalow in the city’s Eastport neighborhood, O’Leary’s smart dining room sets the perfect backdrop for sampling its creative, eclectic seafood. The Jamaican-style salmon with rice and peas, jerk spices and smashed avocado and the grilled scallops with crab risotto and sautéed spinach are just two of delicious options. Finish with an indulgent dessert of bread pudding or Chicago-style cheesecake and wash it down with one of O’Leary’s signature craft cocktails.