Located on the Chesapeake Bay, the historic harbor town of Annapolis has one of the highest concentrations of 18th-century buildings in America—including 50 from the colonial era. (Fun fact: It was briefly the capital of the United States.) The picturesque city is also known for blue crabs, the United States Naval Academy and taverns so old that George Washington partied in them. It’s also an easy drive from Washington, D.C., Philadelphia and Richmond. Here’s how to spend the ideal long weekend in Maryland’s charming capital city.
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Josh BrownExecutive Chef at Level Small Plates Lounge, Vida Taco Bar and The Fox's Den
“Annapolis is a town that has something for everyone; history, culture, arts and an up and coming restaurant scene.”
Canned, pickled and fermented produce are the focus at this rustic and romantic spot run by a husband-and-wife team.
Rams Head Tavern
The brunch here is award winning. Ask for a table on the wisteria-covered patio. Dog owners, rejoice: Pups are welcome—and have their own food menu.
Metropolitan Kitchen & Lounge
This farm-to-table restaurant has a lively outdoor deck and live music nightly.
Jimmy Cantler’s Riverside Inn
Drive across the bridge for steamed hard-shell Maryland crab at this local favorite. Make sure to grab a picnic table overlooking Mill Creek.
You could be sitting next to a millionaire without even knowing it at this low-key neighborhood joint. Order the crab cakes or a grilled cheese sandwich.
Overlooking the Severn River and the Naval Academy, this waterfront seafood-forward hot spot has a panoramic view. Sit on the deck to watch the boats and clouds float by.
Drive toward the Bay Bridge to sample the bakery’s famous seven-layer caramel cake.
Annapolis Farmers’ Market
In the spring and fall, the farmers’ market at the bottom of Main Street hosts hyper-local vendors. Grab everything from flowers to fresh bread.
Annapolis Ice Cream Company
Thirty-six flavors are rotated daily—and made in-house. Watch the shop’s Twitter feed to see if local favorites like apple pie and mint Oreo are on offer.
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Scotlaur Inn Bed & Breakfast
This turn–of–the–20th–century row house has 10 old–fashioned guest rooms in the heart of Annapolis. Guests get a complimentary seat for breakfast at the iconic Chick & Ruth’s Delly downstairs.
Guest rooms date back to the Revolutionary War era (the wooden porches and marble–tiled lobby are Victorian). In fact, 11 delegates of the 1786 U.S. Congress stayed here.
Loews Annapolis Hotel
While its red brick facade blends with the city's 1700s architecture, inside, the property is airy, spacious and modern.
Officially called the City Dock (but nicknamed Ego Alley), it’s prime people– and boat–watching territory. Watch sailboats cruise the river.
U.S. Naval Academy
Visit to the crypt of Revolutionary War hero John Paul Jones on a public tour. Try to time it so you see a daily “formation,” where the entire crowd of nearly 4,000 midshipmen assembles.
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