20 Best Restaurants in Annapolis, Maryland

Vin 909

Vin 909 is a wine bar and restaurant that serves fantastic farm-to-table New American cuisine.

You can’t go wrong with delicious, passionately prepared dishes, such as the Clams & Butternut Squash Curry, Seared Monkfish (in a bacon, mango, and habanero reduction), or the Italian Boar Sandwich.

Or try one of their extremely popular brick-oven pizzas like the Pinnapolis.

Hospitality expert Alex Manfredonia and Executive Chef Justin Moore are the owners of Vin 909. You will love the ever-changing, seasonal menu at this charming eatery, situated in a classic Sears Roebuck house in the eclectic Eastport neighborhood of Annapolis.

909 Bay Ridge Avenue, Annapolis, MD 21403, 410-990-1846

Boatyard Bar & Grill

For some of the freshest local seafood and regional classics, you will want to check out Annapolis’s tasty Boatyard Bar & Grill.

Dive into to their delicious, signature dishes such as Antione’s Stuffed Oysters, Cream of Crab Soup, Finley’s Fantabulous Fish Tacos, or “The Best Crab Sandwich You’ll Ever Eat.” Wash it all down with an ice-cold beer.

Owner Dick Franyo opened Boatyard Bar & Grill in 2001 after retiring from his thriving, 30-year business career.

A favorite of local sailors, fishermen, and food enthusiasts, this friendly eatery is located on Restaurant Row in Annapolis’s historic maritime district of Eastport.

400 Fourth Street, Annapolis, MD 21403, 410-216-6206

Iron Rooster

The popular Iron Rooster restaurant serves a new twist on traditional Southern comfort foods for breakfast (available all day), lunch, supper, or drinks.

Treat yourself to scrumptious grub such as the Smoked Brisket Benedict, Chicken & Waffles, Bacon & Egg Ramen (with sliced pork belly), or the Dixie Pot Roast.

Wash it all down with a refreshing selection or signature cocktail from the bar such as the Cock-A-Doodle-Doo.

Hospitality expert Kyle Algaze first opened Iron Rooster in 2014, pouring all of his passion into the restaurant. Enjoy views of Ego Alley at this outstanding eatery located on downtown Annapolis’s City Dock.

12 Market Space, Annapolis, MD 21401, 410-990-1600

Carpaccio Tuscan Kitchen and Wine Bar

Carpaccio Tuscan Kitchen and Wine Bar is a sophisticated upscale Italian restaurant in Annapolis' vibrant downtown district, originally opened in 2008 as part of the MONTE restaurant group.

The charming restaurant serves up a full menu of authentic Tuscan specialties, including high-quality brick-oven pizzas in flavors ranging from traditional margherita to meat lovers' pizzas prepared with pepperoni, ham, sausage, and bacon. Refined land and sea entree options include seafood fettuccine Mediterraneo, chicken scarpariello, veal porcini, and linguine alle vongole, served up with elegant sides such as roasted brussels sprouts and sauteed broccolini.

Fine Italian-style pasta options include pappardelle bolognese, fettuccine carbonara, and penne pasticcio. A full wine bar offers high-quality imported selections, with discounted pricing offered at happy hour.

1 Park Pl, Annapolis, MD 21401, Phone: 410-268-6569

Galway Bay Irish Pub

Galway Bay Irish Pub is a convivial place where you can eat and drink merrily, enjoying their menu options of Gaelic grub and American standards.

You can’t go wrong with delicious Irish Classics like Oysters O’Leary, Shepherd’s Pie, Corned Beef & Cabbage, or Murphy’s Roast. Many gluten-free options are also available.

Save room for a spectacular dessert like their Irish Egg Nog Spiced Pumpkin Pie! Friends Anthony Clarke and Michael Galoway first opened Galway Bay Irish Pub in 1998. You will find this charming eatery in a beautiful historic building downtown, situated very close to the Naval Academy in Annapolis.

63 Maryland Avenue, Annapolis, MD 21401, 410-263-8333

Mason’s Famous Lobster Rolls

If you’re in the mood for lobster, you simply must visit the quaint yet incredible Mason’s Famous Lobster Rolls. Whether you order the Lobstah BLT, Connecticut Roll, Lobstah Bisque, or the Maine Lobster Salad Roll, your taste buds are sure to thank you! All of Mason’s lobsters are directly from Maine after being exclusively caught by a small fleet of ships.

Restaurateur Dan Beck and his wife open this charming eatery, which has been open since 2015. They named the place after their son. Enjoy the friendly atmosphere at Mason’s Famous Lobster Rolls, located across the street from the Maryland State House.

180 Main Street, Annapolis, MD 21401, 410-280-2254

Jimmy Cantler’s Riverside Inn

Maryland’s iconic, waterfront Jimmy Cantler’s Riverside Inn serves incredible, fresh seafood, and they specialize in crabs. Savor delicious, passionately prepared dishes such as Jimmy’s Steamed Snow Crab, Spicy Oyster Po’Boy, Crab Mac ‘N Cheese, or the breaded Clam Strips. You simply can’t leave until you try their famous Maryland blue crabs.

Former Chesapeake Bay waterman Jimmy Cantler opened this renowned restaurant in 1974 with the help of his lovely wife Linda. Grab yourself a little slice of heaven in the form of some amazing seafood at Jimmy Cantler’s Riverside Inn, located in Mill Creek – just minutes from the Annapolis City Dock.

458 Forest Beach Road, Annapolis, MD 21409, 410-757-1311

Red Red Wine Bar

Red Red Wine Bar doesn’t only offer a great wine program, but they also serve delicious New American cuisine. Savor incredible, boldly flavored dishes like Bacon-Wrapped Stuffed Shrimp, Manchego Chicken Panini, Braised Lamb Shank, or Maryland Crab Soup.

Or stop in for the New Orleans Sunday Brunch & Champagne Bar and try the Shrimp Creole Omelette. Restaurateur power couple Brian (a former DC news anchor) and Lisa Bolter are the owners of Red Red Wine Bar, which has been open since 2011. Come for the wine and stay for the food at this hip hangout located across the street from the Maryland State House.

189B Main Street, Annapolis, MD 21401, 410-990-1144

Miss Shirley’s

Miss Shirley’s Cafe serves delicious American classics with Southern influences. Dive into tasty dishes like Fried Green Tomatoes, S’mores Baked Banana Skillet, Down on the Bayou Benedict, or Bubba’s Slider Trio.

Delicious craft cocktails are also available. Baltimore native Eddie Dopkin opened the original Miss Shirley’s in Baltimore in 2005. He named it after an amazing cook, Miss Shirley Mc Dowell, a staple in the Baltimore culinary community. You will find this upscale-casual eatery nestled between College Creek and Old Woman’s Cove.

1 Park Place, Annapolis, MD 21401, 410-268-5171

Carrol’s Creek Cafe

Enjoy a fabulous waterfront dining experience overlooking Spa Creek at the upscale Carrol’s Creek Cafe, which serves incredible seafood and classic Chesapeake fare. Savor unbelievable, expertly prepared dishes such as the Pepper Crusted Beef Tenderloin Carpaccio, Lobster & Black Truffle Pot Pie, or Seasonal Vegetable & Mushroom Risotto.

Or pop in for breakfast and try the Tortilla Casserole! They also have a splendid wine program with plenty of options to accompany your meal. The iconic Carrol’s Creek Café has been open since 1983 and is owned and run by Jeffrey Jacobs and his beautiful family. You will find this classy restaurant in Annapolis’s Eastport neighborhood.

410 Severn Avenue, Annapolis, MD 21403, 410-263-8102

Osteria 177

Enjoy a beautiful, intimate night at Annapolis’s elegant and renowned Osteria 177, which specializes in Italian coastal cuisine and spectacular wine. Savor unbelievable, passionately prepared dishes like Penne Con Polpa di Granchio e Arugola, Scampi alla Pescarese, Pollo al Marsala, or a Gypsy Chicken Panini.

Be sure to try something delicious from their extraordinary wine list! The Italian-born owner and chef Arturo Ottaviano first opened Osteria 177 in 2006, and it has since become a local favorite thanks to his tasty culinary creations. This sophisticated restaurant is located downtown close to Maryland State House and the Naval Academy.

177 Main Street, Annapolis, MD 21401, 410-267-7700

Sin Fronteras Cafe

Sin Fronteras Cafe serves excellent Mexican and Latin cuisine with a Miami flare. Treat yourself to extraordinary, boldly flavored dishes like the Peruvian Lomo Saltado, Margarita Salmon, Pork Chop a la Mamajuana, or Chicharron en Salsa Verde.

Be sure to try one of their signature margaritas – they’re said to be the best in town! Restaurateur friends Walter Vasquez and Wilmer Romero opened Sin Fronteras in 2014. Enjoy the fun and friendly atmosphere at this spectacular restaurant located close to the Annapolis Towne Center.

2129 Forest Drive, Annapolis, MD 21401, 410-266-0013

Dry 85

Dry 85 restaurant specializes in extraordinary drinks and delicious, modern twists on American comfort food. Treat yourself to amazing dishes like the Blue Cheese and Fig Burger, Fried Oyster Po Boy Sliders, or Slow-Roasted Pork Ribs with Housemade Blueberry Sauce. Wash it all down with a fine bourbon or a refreshing craft beer.

Stop in for brunch and try the Hogs ‘n Hops! News anchor-turned-restaurateur Brian Bolter and his wife Lisa opened Dry 85 in 2014. The restaurant is modeled after a Prohibition-era speakeasy, and you will find this fine establishment in a back alley garage near State Circle and the Naval Academy.

193B Main Street, Annapolis, MD 21401, 443-214-5171

Cafe Normandie

Cafe Normandie specializes in phenomenal French Country Cuisine with Maryland seafood specialties. Savor unbelievable and passionately prepared dishes such as the Apple Cheddar Crepe, Salmon with Blueberries, or Angus Steak with Bordelaise Sauce. Or stop in for breakfast and try the tasty Eggs Florentine.

Everything is made from locally sourced, sustainable ingredients, meaning you can enjoy your meal and support the community at the same time. An impressive wine list is also available. Best Chefs America Award-winning Chef Jean Louis Evennou (a native of France) first opened Café Normandie in 1986. He pours his heart into every dish he makes. Enjoy the cozy atmosphere at this charming eatery located in the heart of downtown Annapolis.

185 Main Street, Annapolis, MD 21401, 410-263-3382

O’Leary’s Seafood

O’Leary’s Seafood serves some of the best seafood the city has to offer – it is freshly caught and prepared to perfection. You can’t go wrong with incredible, expertly prepared dishes such as Bronzino Tripoli, Jamaican Salmon, Pork Frites, or Sopa de Mariscos. Or stop in for brunch and try the Blue Ridge Benny.

Choose something cold and refreshing from the tempting wine and cocktail program to complete your meal. Owner Wil Peterson first opened O’Leary's Seafood in 1983, and it has since become a popular local eatery. You will find it in a charming old house near Horn Point.

310 Third Street, Annapolis, MD 21403, 410-263-0884

Federal House Bar & Grille

Annapolis’s landmark Federal House Bar & Grille serves up incredible, award-winning New American cuisine. Savor delicious, expertly prepared dishes like their famous Cream of Crab Soup, Baked Stuffed Flounder, Chicken Diablo, or Guinness Braised Pot Roast. In addition to a nice wine list, they also have 25 beers on tap, a full bar, and occasional live music and DJs.

Bring Fido with you to enjoy a nice meal on the pet-friendly patio – they even have a Doggie Menu! This iconic restaurant is located inside the Federal House, established in 1830. You will find it on Market Space in the Annapolis Harbor.

22 Market Place, Annapolis, MD 21401, 410-268-2576

Davis’s Pub

Davis’s Pub is a popular hangout that serves creative pub fare and has been featured on The Food Network’s “Diners, Drive-Ins, and Dives” with Guy Fieri. Treat yourself to fantastic foods like the Crab Cake Sandwich, Pulled Pork Barbeque Sandwich, Chesapeake Bay Retriever Sandwich, or Chicken Tostadas.

Don’t miss the Fried Pickles! Wash it all down with a refreshing draft beer. Originally founded as a general store in the 1920s (and later a lounge in the 1940s), it later became Davis’s Pub in the 1980s. Today, Lee and Michaela Troutman are the happy owners of the pub, which you will find in the Eastport community.

400 Chester Avenue, Annapolis, MD 21403, 410-268-7432

McGarvey’s Saloon & Oyster Bar

For the best night out, you will want to check out Annapolis’s popular McGarvey’s Saloon & Oyster Bar, which serves scrumptious pub fare in addition to selections from its raw bar menu. Start your meal off with the Crab Balls appetizer before diving into incredible dishes like Sesame Seed Fried Flounder, Fresh New England Sea Scallop, or a Bacon & French Roquefort Burger.

Grab a refreshing craft beer and enjoy the live music (every Friday and Saturday night). Local hero Mike Ashford first opened McGarvey’s in 1975. Check out this hip hangout downtown, very close to the Annapolis City Dock.

8 Market Space, Annapolis, MD 21401, 410-263-5700

Chick and Ruth’s

Chick and Ruth’s serves incredible sandwiches, old-fashioned milkshakes, ice cream, and baked goods. Get your grub on with delicious treats like the Super Duper Colossal three-pound burger, Corned Beef Sandwich, or the Jumbo Lump Crab Cake Wrap.

Or stop in early and try the Homemade Sausage Biscuits & Gravy. Open for decades, the Delly was originally founded by Chick and Ruth Levitt and sits in a historic building that also houses the owners’ Scotlauer Inn Bed & Breakfast. You will find Chick and Ruth’s downtown close to the Maryland State House.

165 Main Street, Annapolis, MD 21401, 410-269-6737

Joss Cafe & Sushi Bar

The popular Joss Cafe & Sushi Bar offers incredible Japanese eats. Savor a tasty selection from the sushi bar such as the Maguro Poke or the Mediterranean Sashimi.

Or try something from their other menu like Chili Scallop Wontons or Pan Fried Dumplings. Joss Café and Sushi Bar has been open since 1991. Enjoy this warm and friendly eatery located right across the street from the Maryland State House and State Circle.

195 Main Street, Annapolis, MD 21401, 410-263-4688