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Anchors Aweigh: Annapolis Sets Sail in Fall

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By Joanna Theiss

From big universities to small liberal arts colleges, college towns often share the same features: crowded coffee shops, bars with cheap beer specials, and students lugging backpacks or lounging on wide green lawns.

The moment you step into Annapolis, Maryland, your every sense tells you that this place is different. 

Perched between the Chesapeake Bay and the mouth of the Severn River, the air here smells like brackish water and frying crab cakes generously seasoned with Old Bay, Maryland’s iconic seasoning blend. The ringing of chapel bells from a colonial-era house of worship mingles with the cheers of Navy football fans watching the annual face-off against Army at one of the many bars in Market Space, just feet from the harbor. 

Then there is the sight that truly sets Annapolis apart: the presence of uniformed midshipmen. At the U.S. Naval Academy, located in the heart of Annapolis, the enrolled students – and with a nine percent acceptance rate, it’s an elite bunch – graduate with commissions as either ensigns in the Navy or second lieutenants in the Marine Corps. Their course of study is rigorous, with a Plebe Summer, mandatory participation in athletics, and the upright demeanor required of active-duty midshipmen; although, they, too, often take advantage of Annapolis’ offerings. You’ll stand behind midshipmen in line at Annapolis Ice Cream Company or scoot around them as they study in the quirky, low-ceilinged basement rooms of Old Fox Books. 

The Mids are hard to miss in Annapolis, but there is another major college presence in town: the Johnnies.

While much smaller than the Naval Academy, St. John’s College is also integrated into Annapolis life. In the fall, the Johnnies can be found under the turning foliage on the lawn of McDowell Hall, located near the Maryland State House, which dates from the 1770s. They’re dutifully working through the college’s Great Books curriculum, which requires the study of classics through twenty-first century writings, with a heavy emphasis on arts, debate, and culture. 

Despite the differences between the Naval Academy and St. John’s, Annapolis is peacefully inhabited by the undergraduates. The spring croquet match brings the Johnnies and the Mids together for good-spirited competition, and a recent agreement between the schools has meant that the Johnnies are now working retail at the Yard, filling the slots left open by the Mids who aren’t permitted to have outside employment.

Because of Annapolis’ small size, visitors can easily explore both campuses. At St. John’s, follow in the footsteps of General George Washington, who visited the college in 1791, and stick around for a performance of the college theater troupe, the King William Players, whose recent performances include both Shakespeare and a modern romantic comedy. 

From the campus buildings of St. John’s College, head south on King George Street, which is lined with eighteenth-century row houses that open directly onto the sidewalk. Here, civilians can enter the Yard and take in the Naval Academy’s impressive visitor’s center, which provides a thorough overview of the institution’s history beginning with its establishment in 1845. Yard highlights include the 1911 Navy B-1 replica suspended from the ceiling at Dahlgren Hall and the replica Gokoku-ji Bell, rung whenever Navy’s football team beats Army. 

After the Yard, you’ll be drawn back to the harbor, where flashy yachts and modest fishing boats slip into the dock just feet from the busy pedestrian plaza. It’s this connection to the waterways that makes Annapolis a true sailing capital and a natural home for the United States Sailboat Show, which takes place in mid-October and lures aficionados from all over the world. Opportunities to set sail abound, or you can just hop on a water taxi for a hassle-free way to explore. 

Bring an appetite for your trip across the short bridge to Eastport, where Restaurant Row includes some of the town’s best restaurants. Seafood is Annapolis’ main culinary draw, and many of the restaurants pay their respect to the seabed by recycling oyster shells, which are then used to plant new aquatic life in the Bay. 

From chiming bells to cramming undergrads, from Navy football to Shakespeare, Annapolis in fall is a sensory treat for all tastes.