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Travel: Annapolis Mixes American History with Contemporary Entertainment & Food

Walker Evans Walker Evans Travel: Annapolis Mixes American History with Contemporary Entertainment & FoodAll photos by Walker Evans.
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Geographically speaking, Annapolis, Maryland has roughly the same population as Delaware, Ohio. That fact alone may make it sound like a strange place for a vacation destination, but in terms of American history and leisure activities, Annapolis punches well above its weight. A representative from their visitors bureau recently reached out to Columbus Underground about coordinating a trip there this summer, and we jumped at the chance to become more familiar with this significant East Coast city.

With only a seven hour drive separating the capital of Maryland from the capital of Ohio, Annapolis is an easy destination for an extended weekend visit. Located on the Chesapeake Bay, Annapolis is one of the birthplaces of American Democracy with a rich history in the seafood and ship building industries. While much of that industry has declined over the past century, Annapolis has found a new life as a tourism destination, offering both historic and modern opportunities for people of all ages to engage with.

Getting Around

The easiest way to get around Annapolis is on foot. The city proper clocks in at a compact eight square miles, and if your trips are limited to the immediate Downtown area, you’ll find most popular destinations within a 20 minute stroll. Another alternative is to hop aboard the Annapolis Circulator, a free bus that runs a 20 minute loop through the Downtown area.

Of course, if you need to travel further and faster, the coolest way to get around is by water taxi. Local company Watermark operates the service, which can be called up to schedule a ride, or boarded casually at docking locations. Trips range from $3 to $8 per person depending on how far you plan to travel, and guides offer friendly advice to tourists looking for places to eat or activities to engage in.

Another easy way to take in the sights around town is by way of eCruiser. Annapolis touring company Urban EvenTours offers several guided tours that focus on history, architecture and food. The openness of the vehicles provide ease for your photo-taking and sight-seeing while drivers narrate the important stops along the way.

Things to Do

Main Street is your main drag if you’re interested in strolling and shopping in Annapolis. This third-of-a-mile stretch features a mix of restaurants (more on that later), art galleries, boutique shopping and entertainment destinations. Families with smaller children might enjoy a stop at The Clay Bakers, where you can paint pottery, while bigger kids (and adults) might want to pop inside Capital Comics to pick up a graphic novel or comic-related paraphernalia. If you’re looking for a souvenir or two, shops range from upscale and unique to cheap and novelty, providing options for just about everyone.

Once you make your way down to the water, there’s plenty of aquatic activity to be found as well. Strolling the various piers and docks can be fun in its own right, admiring both the more traditional sailboats and the multi-million dollar yachts that are parked for the day. While you can certainly charter your own boat, an easier and cheaper option to get out into the water is by way of kayak, canoe or paddle board. The guys at Annapolis Canoe & Kayak are super friendly with novices and quick to get people out and having a good time. Their location in Eastport also provides easy access to both the calmer waters upstream in spa creek and the choppier and busier waters in the harbor for anyone looking for more of a challenge.

West Street is another main drag in Downtown Annapolis where entertainment abounds. In addition to several art galleries and shops, you’ll find day spas and escape rooms. Throughout the summer, a collection of restaurants on West Street shut the street down to car traffic every Wednesday night (weather permitting) for Dinner Under the Stars, which has turned just as much into a social gathering as it is a foodie event. Live music lines the street to compliment the extended patio service. And speaking of places to eat…

Places to Eat

First things first. When anyone thinks of the Chesapeake Bay, they think of oysters and crabs. While the fishing industry in the bay area has declined over the past century, there is still plenty of local seafood to be found in area restaurants.

The Boatyard Bar & Grill has been an Eastport staple since 2001, serving up breakfast, lunch, brunch, happy hour and dinner menus in a large indoor/outdoor dining area just a block from spa creek. Their raw bar features local daily specials (pictured below), while crab lovers can find soups, cakes, dips, fried balls, salads, sandwiches and more.

If you’re looking for something a little more upscale in Eastport, check out Carrol’s Creek Cafe. This dock-side dining room opened in 1983, and maintains many of its classic dishes from opening day. Fresh salads are made to order table-side while patrons can watch boats come and go from the surrounding piers. If you’re looking for something a bit more exciting, Carrol’s offers a front row seat for the Wednesday night sailboat races. A highly recommended dish from the menu is the Rockfish Fillet — a local name applied to striped bass — caught fresh from the bay.

No trip to Annapolis would be complete without a stop at Chick & Ruth’s Delly, best described as a diner-meets-delicatessen with an East Coast twist. Their expansive menu includes everything from greasy spoon breakfast to kosher corned beef sandwiches to six pound milkshakes ($19 each) to two dozen types of pies made daily. If you’re a fan of savory breakfast, you can’t beat the Jumbo Lump Crab Cake Eggs Benedict. Just make sure you arrive before 8:30am on a weekday (or 9:30am on weekends) so you can take part in the daily reciting of the pledge of allegiance.

If you’re looking for something a bit less touristy, Annapolis has grown its foodie scene in recent years to appeal to a wider variety of tastebuds that seek something beyond crab cakes. Main Street is lined with options that range from hip taco bars (Vida) to French cuisine (Cafe Normandy) to chef-centric American concepts where pickling and fermentation is the theme (Preserve).

One of our stops included Iron Rooster, a breakfast-all-day joint near City Dock that features Americana classics (biscuits and gravy) next to hip brunch trends (chicken and waffles, breakfast burritos). Of course, you can still find crabmeat-laden dishes all over the menu, but you should definitely save room for the Housemade Pop-Tart of the day (berry edition — pictured below). They come with a hefty seven dollar price tag, but are large enough for two or three people to share.

Of course, a trip to the state capital wouldn’t be complete without at least one slice of Smith Island Cake, the official dessert of Maryland. The traditional version of this dish features eight to ten layers of yellow cake with chocolate frosting in between. It can be found on menus all throughout town, with our own delicious slice coming from the Smith Island Baking Company, courtesy of a stop inside the tiny Leeward Market Café and Grocery in Eastport.

Places to See

If you’re interested in American history from the colonial era, there are few places better than Maryland to take it in. The city served as the capital of the United States, and an important meeting place for the founding fathers in the late 18th century. The Maryland State House (pictured below) has been in continual legislative use since 1772, serving as the place where George Washington resigned from duty as the commander of the Continental Army. Self-guided tours are available for those interested in taking a deeper dive into the building’s history.

Architecture fans will also enjoy touring Annapolis, which is home to many nationally historic buildings and monuments. The homes of multiple signers of the Declaration of Independences are still standing in well preserved conditions, including the William Paca House and Garden (pictured below). Additional worthwhile landmarks open for tours include the Chase-Lloyd House (home to signer Samuel Chase), the United States Naval Academy, and the Banneker-Douglass Museum, which features African-American heritage, history and culture.

To get a sense of the scope and scale of the fishing and seafood industry that was once a driving force for the city, visitors can stop by the Annapolis Maritime Museum, housed in the former McNasby’s Oyster shucking house in the Eastport neighborhood. The space showcases images, tools and boating equipment from generations past in a dedicated space, while another portion of the building is open for art gallery installations and private event venue rentals. The docks surrounding the museum offer some of the city’s best views out into the bay.

For more information, visit www.visitannapolis.org.

NOTE: This trip was made possible by our friends at Visit Annapolis, who provided Columbus Underground with itineraries, tours scheduling, hotel accommodations and a portion of the food and entertainment accommodations.

All photos by Walker Evans.

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