Annapolis, sea-side capital of the state of Maryland, is a colonial American jewel box. Cobblestone streets lead from the Maryland State House, whose white dome peeks over centuries-old brownstones, down to the sailboat-filled harbor. The main thoroughfare is lined with quaint shops and restaurants; a few chains, yes, but mostly unique local establishments. Despite the mid-autumn chill in the air and precipitation that ranged from fine mist to light drizzle, it was still pleasant to walk around.
When Annapolis was founded in the mid-17th century, it was a royal colony of Great Britain. (Fun fact: Annapolis was named after Princess Anne, the first queen of the Kingdom of Great Britain. England and Scotland became unified during her rule.) Many of the well-preserved buildings bear plaques attesting to their age and in some respects it seems like not much has changed over the years. Take away the cars and you can almost hear the clop-clop of horses pulling carriages down the road.
Once a port-of-call in the slave trade, the quiet beauty of Annapolis Harbor belies its dark past. Today Annapolis is known as “America’s Sailing Capital” and is popular for its sailboat races. Even on non-race days, you’re almost guaranteed to see boats gliding along the horizon.
Annapolis is also home to the U.S. Naval Academy, an American institution that has been educating new classes of military officers since 1845. Visit during the fall, and you’ll find flags supporting the Navy football team flying all over town. If you like a man in uniform, this is the place for you!
During our visit, one street was bedecked with colorful chicken statues, part of an installation called “Hatching the Arts,” aimed at revitalizing the Annapolis arts district. I particularly enjoyed the little backpacker whose plaque read, “The world is my classroom.”
Dining options abound, especially on busy Main Street. The Red Red Wine Bar, as its name suggests, is an excellent place for a glass of vino. Interestingly, the bar keeps the wine on tap to simulate the experience of enjoying it straight from the barrel. The interior is warm and bright with funky decor and cozy plush seating from which you can enjoy a wine tasting and dishes made with Maryland crab. Actor Kevin Spacey has even visited this trendy spot!
Across the street, Piccola Roma serves up hearty Italian fare in a more intimate setting. We started with caprese salad with giant slices of fresh buffalo mozzarella and succulent bacon wrapped dates stuffed with goat cheese and drizzled with aged balsamic. Our entrees were even better: a creamy and tender seafood risotto and a crab ravioli in a delectable vodka sauce.
To fully appreciate the old world charm of Annapolis, I recommend having afternoon tea at Reynold’s Tavern. Built in 1737, it’s one of the oldest pubs in America and certain to transport you to another era. The dark wood floors and heavy furnishings exude 18th-century rusticity while white walls and gold-framed paintings keep the space from feeling drab. Tea was served on delicate and brightly painted china, with the snacks presented on a three-tier tray. Warm pies were a welcome addition to the traditional savory sandwiches and the hummingbird cake was a true sweet treat. But what really made this afternoon special was the selection of Jane Austen-inspired teas, in honor of the 200th anniversary of Pride & Prejudice. I chose the Mr. Darcy blend, which, like the character himself, took some getting used to but ultimately satisfied.
Red Red Wine Bar Address: 189 Main St, Annapolis, Maryland Pricing: Appetizers US$6-13; Wine flights average US$9-12
Piccola Roma Address: 200 Main St, Annapolis, Maryland Pricing: Dishes between US$7-23
Reynold's Tavern Address: 7 Church Circle, Annapolis, Maryland Pricing: Afternoon tea is US$18