Nearby Annapolis is a legendary port—in part because it’s home to the U.S. Naval Academy. When you’re there, it’s easy to work up an appetite taking historic walking tours, boating on the Severn River, or just meandering around the beautiful streets. Here are 5 of our favorite Annapolis restaurants you’re guaranteed to love…
The Boatyard was founded in 2001 by Owner Dick Franyo. His love of Chesapeake Bay lifestyle and other ports where Chesapeake sailors and fishermen frequented have informed the décor of this outstanding Annapolis restaurant. You’ll see pictures of local sailors along the walls and fish caught by local fishing friends are hung in the Boatyard’s Pilar Bar, named after Hemmingway’s fishing boat
The the Boatyard is just a short walk or water taxi ride from Annapolis City Docks. The interior gives the feeling of an old yacht, with shiny white walls, mahogany, sea foam green ceilings and large wooden beams.
Locals come here to share pints, great crab cakes and the freshest local seafood. Specialties include smoked fish of the day, cream of crab and Maryland crab soups and an extensive list of crab and seafood specialties. What makes The Boatyard really stand out from other Annapolis restaurants? It has the most extensive raw bar in the area including a variety of oysters, clams, shrimp and mussels.
What’s more, this restaurant recycles just about everything, including its food scraps that go to composting…even the oyster shells are collected by the Oyster Recovery Program.
Charles Carroll of Carrollton was Maryland’s most famous signer of the Declaration of Independence. Located on Spa Creek, Carrol’s Creek does not take the heritage of its name lightly. This Annapolis restaurant’s historic location overlooks the waters of one of America’s most charming and historic cities. And it serves up the riches of the bay and the land in a new American style of cooking..
A great special: come for dinner any Tuesday evening and enjoy a bottle of your favorite wine at half the regular price. (This offer is only valid in the dining room.) The Jumbo Lump Crab Cakes are a standout menu item—which is saying something since almost all Annapolis restaurants feature excellent seafood.
The Galway Bay Irish Pub is located on Maryland Avenue in downtown Annapolis in a beautifully historic building. The relaxed and happy atmosphere of this Annapolis restaurant harkens back to the jovial camaraderie among sailors particularly of Irish descent.
You can relax in the traditional Irish Pub or enjoy a family meal in the brick-walled Dining Room. The Shepherd’s Pie is an outstanding version of a traditional favorite.
O’Leary’s is another Irish-named Annapolis restaurant, but this is a more upscale dining experience. The menu is jam-packed with absolutely incredible riffs on local, fresh seafood.
Of course the crab cakes are a must-try—at O’Leary’s, they’re served with fingerling potatoes in a warm applewood bacon, onion and scallion vinaigrette, and haricot verts. The Southern favorite shrimp and grits get an update with Tasso ham, mixed bell peppers and garlic over cheddar and jalapeno grits, finished with butter beer sauce. Or get a taste of the Caribbean with jerk spice encrusted Atlantic salmon over Jamaican rice and peas with house smashed avocado, jumbo lump crab meat, and grilled asparagus.
O’Leary’s is so sure of its excellence, it even links directly to current reviews on its webpage.
Another of the Annapolis restaurants that takes its environmental impact seriously, Level Small Plates Lounge sources from local farms and businesses and has a robust recycling program. The food is also pretty darn outstanding.
So what is a small plates lounge? Well, the menu items are designed to be shared, and are both Chesapeake and Mediterranean inspired.
Level was established by five local friends and colleagues with the hopes of developing a locals first atmosphere with welcoming attitudes to all. The cocktails are all handcrafted with fresh juices, mixes, and garnishes.
We hope you’ll choose The Wayside Inn as your base for upcoming Maryland trips. Conveniently located near Annapolis, Baltimore and Washington DC, our hometown Ellicott City is a worthy destination in itself. Download a free area vacation guide to help plan your trip. And you can start your day of sightseeing off right with our delicious breakfast service.