Annapolis city dock- skyline at Chesapeake Bay with the United States Naval Academy Chapel dome
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Exploring Annapolis City Dock & Harbor: Where Colonial History Meets Waterfront Charm

On the Water and the Center of Action in Annapolis for Centuries 

Annapolis City Dock is more than just a picturesque harbor – known as the “historic heart” of our city. It’s a vibrant place with nearly 400 years of history. Formed in the early 1600s, it was one of the central hubs for shipping and trading goods along the eastern seaboard, served by the convenient location of Annapolis and providing quick access to the larger Chesapeake Bay. During the 1700s and 1800s, City Dock expanded even more in size and importance, becoming a hotspot for ship-building, seafood processing, and urbanization into the 20th century as Annapolis’ population grew. Today, that historical ambiance lives on amidst more modern sights like luxury yachts, guided boat tours, and special events, continuing to play a vital cultural role. Our historic Annapolis bed and breakfast, just a stone’s throw away from the waterfront, offers the perfect home base from which to explore the City Dock. So, whether you’re a sailboat aficionado, maritime history buff, or just looking to enjoy the pristine scenery and a delicious meal, it’s all just a short stroll away.
boats docked in the Chesapeake Bay harbor in Annapolis City Dock

Exploring City Dock on Foot, Joining Water Tours, and Attending Sailboat Shows

Boats of all shapes and sizes command the horizon at Annapolis City Dock, with rows of slips along “Ego Alley,” the main approach for boats coming and going throughout the day. Walking along the waterline, you’ll see every type of boat from classic-style sailboats to the most modern yachts with state-of-the-art amenities. Look out for unique opportunities to step aboard and tour historic boats like the Pride of Baltimore II, a replica of a storied Baltimore schooner that sailed in the early 1800s, its topsails towering high above. Its ship and crew head out to harbors worldwide as an educational exhibit, including stops during several weekends at City Dock, where you can take a free deck tour, so check their calendar for upcoming visits.

If seeing all the boats up close inspires you to get out on the water, City Dock is the departure location of most Annapolis water tours. You’ll have endless options, from the Chesapeake Bay Bridge, Severn River, and Spa Creek tours Watermark offers to sail outings aboard Woodwind Schooner’s two breathtaking 74-foot sailboats. To ramp up the excitement level, join their public cruise on Wednesday nights during the summer sailing season, when you’ll join the Woodwind crew as they race against other sailboat teams in the harbor, a rare chance to experience the thrill of high-stakes racing even if you have no sailing experience.

During several weeks of the year, Annapolis celebrates all things sailing, attracting visitors from around the globe for renowned sailboat shows. At all three of the main events—the Spring Sailboat Show in late April, the Annapolis Powerboat Show in early October, and the fall Annapolis Sailboat Show in mid-October—you’ll have the opportunity to see the most current trends in sailboat design, browse company exhibits, chat with the pros, and learn from various educational seminars. An established tradition for over 50 years, these weeks are always popular, so get your luxurious Lodging in Annapolis, Maryland squared away far in advance.

Special Events and Attractions Year-Round at City Dock​

Although undoubtedly a prime destination for boat enthusiasts, Annapolis City Dock isn’t just about sailing – it’s also where community-minded and fun-filled events happen every season throughout the year. During spring, when all of Annapolis celebrates the newest round of United States Naval Academy graduates during commissioning week, the dock waterfront is one of the best places to see the annual Blue Angels fly-over in the skies above Annapolis Harbor. In the summertime, City Dock hosts the Juneteenth parade in late June, commemorating African-American heritage and their emancipation that arrived with the end of the Civil War. Soon after, 4th of July brings a full day of festivities along the water, including an evening parade, marching bands, and fireworks over the downtown historic district. Later in the year, the winter calendar fills in with beloved City Dock traditions like the massive, lighted Christmas Tree and unique Annapolis holiday pastimes such as the Parade of Lights, when hundreds of boats decorated with lights sail by while crowds line City Dock and nearby Spa Creek bridge.

You’ll also find other attractions worth visiting at City Dock, such as the Museum of Historic Annapolis, where you can dive into the fascinating historical chapters of our city, tracing back to when Annapolis briefly served as the nation’s capital. With our nearly 250-year-old Maryland State House, quaint brick-lined streets, and a mixture of Georgian, Colonial, and Victorian architecture, history abounds downtown. Declared a National Historic District in 1965, this museum is a great place to start for history lovers, followed by touring the State House just a few blocks away.

Attend one of the Annapolis Summer Garden Theater (ASGT) evening performances for a cultural twist. Performing on its outdoor stage at City Dock since 1967, ASGT is an institution of Annapolis arts and culture and stage excellence. Attracting cast members from Broadway and beyond to spend their summers performing on the water, it’s a magical place to see live theater under the stars. The upcoming summer 2024 calendar includes the Prom, a lighthearted romp about a small-town dance that runs through mid-June, followed by Escape to Margaritaville from late June through late July, a musical comedy paying homage to Jimmy Buffet’s epic career on and off the stage.

Seafood platter served in Annapolis city dock

Culinary Treats and Cocktails – Dining and Happy Hour on the Waterfront

From a relaxed brunch on a patio overlooking the harbor to an exquisite seafood dinner or more casual evening drinks, City Dock covers all the bases, a microcosm of Annapolis’ diverse restaurant scene. Seafood reigns supreme at most places, including O’Brien’s, proudly “Annapolis’ original oyster bar and seafood tavern.” Start with succulent crab cakes or decadent Chesapeake mussels prepared in garlic and white wine, followed by entrees like seared yellowfish tuna. If seafood isn’t your top choice, order their steak frites, prime rib burger, or chipotle-seasoned chicken breast. Their weekday happy hour from 2-6 pm is perfect for trying all the legendary Chesapeake Bay seafood classics, like a ½ pound of steamed shrimp or a half dozen Orchard Point oysters. Take advantage of their brunch specials with bottomless mimosas and bloody marys on the weekends.

At Choptank, located directly on the dock, grab a table on their upstairs patio deck overlooking the boats below, where you can savor the view alongside rock shrimp ceviche, warm lobster rolls, and steamed hard-shell blue crabs while sipping on one of their eight signature cocktails. Another great option is Latitude 38, whose massive dining room windows look out over the harbor, and their menu includes three cheese crab dips, blackened mahi mahi, various burgers, and four entree-sized salads.

For a more casual snack while you’re walking along the dock or heading over for a USNA walking tour (easily accessible right off Prince George St, where one edge of the Yard directly neighbors City Dock), stop by Sofi’s Crepes for a tasty bacon, avocado, and tomato wrap. And if you’re just looking for a drink in a lively atmosphere, head over to Dock St Bar and Grill, where their second-story room has excellent views. Check out the Navy memorabilia covering their walls, sip on a local microbrew, and enjoy the live music featured on weekend evenings.

Stay with us and explore Annapolis City Dock, where history, culture, seasonal events, and delicious eateries are all framed by the harbor’s beautiful backdrop!