Exploring the Culinary Scene 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