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Annapolis, Maryland: Insider View

by Lenny Rudow

If you’re taking your bareboat charter to or from Annapolis, or you’re just passing through, there are plenty of restaurants, landmarks, and shops to see. But if you stay locked into the downtown area, you’ll miss out on some of the Chesapeake experiences that locals love, and tourists rarely find.

annapolis maryland

The view of Annapolis, Maryland, from the harbor. There's plenty to see and do within walking distance of these docks, but venturing a bit farther from the center of town has its rewards.

Food – There are dozens of good restaurants within walking distance of the downtown moorings, which a water-taxi will be happy to shuttle you to and from. Excellent sushi (try Joss, two blocks up on Main Street), great French cuisine (the Treaty of Paris on Church Circle), and simple casual dining (the Dock Street Bar and Grill, which is naturally located on Dock Street). But for a real taste of Maryland, drop the mooring, and head up Mill Creek to Cantler’s Riverside Inn. Pull into their docks, walk up the concrete steps, and you’ll be in for home-cooked Chesapeake seafood at its best.

Steamed crabs are, naturally, the local favorite. But don’t forget to order a bucket of “steamers,” clams that you rinse in broth then dip in drawn butter. Rockfish (the local name for striped bass) stuffed with crab imperial is another hometown favorite.

Night Life – The downtown area is not at all short on night-life, as anyone who’s ever tried the “Pain Killers” (a concoction consisting mostly of rum) at Pussers, or visited McGarvey’s Saloon, can attest. A bit farther from the harbor, however, this town has a lot more to offer. One place out-of-towners might miss is the Ram’s Head on West Street, about a 10 minute walk from the harbor (stroll up the hill to Church Circle, turn left, then turn left again at West Street). The Ram’s Head is unique for its Ram’s Head On Stage musical events, which include surprisingly well-known bands and soloists playing in an extremely up close and personal venue. Time your arrival right, and you might even be able to catch O’Mally’s March, the Celtic Fusion band led by the Governor of Maryland, Martin O’Malley.

Other Attractions – Naturally, visitors often go to the Annapolis Maritime Museum, on Second Street. Those with kids aboard may also want to stop by the Chesapeake Children’s Museum, with its live animals, nature trails, and the “help yourself” visual art workspace. But another site of interest is the Chesapeake Bay Foundation’s Phillip Merrill Center, one of the world’s most energy-efficient buildings, which houses the offices of the Foundation. (Tours must be scheduled ahead of time by contacting CBF, and you will need to take a 10 to 15 minute cab ride to get there). Another local point of interest is the Naval Academy, an American icon rich with history, which has a visitor center and guided walking tours.

steamed crabs

The local favorite, steamed crabs, may look a bit odd to a first-timer.

Okay, it’s time for a bit of full disclosure: I’m a local, and have been living on the outskirts of Annapolis for over two decades. So yes, I may look at this town with rose-colored glasses. But I know from talking with countless visitors that this is a great place to visit, and it makes for an excellent charter destination. So the next time you’re in town, make sure you take the time to see some of our local highlights—and make sure you order the steamed crabs.

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