Top 15 Must-See Attractions in Annapolis, Maryland

Named after Anne, Queen of Great Britain (1665-1714), Maryland’s state capital has a rich history that emerged in the 17th century and still showcases a wealth of historic architecture.

As you navigate the streets of the Colonial Annapolis Historic District, you’ll discover a prosperous Georgian city, converging around grand circles, including one that encloses the oldest functioning state capitol in the United States.

Dubbed “America’s Sailing Capital,” the city exudes a vibrant nautical culture, characterized by boat shows, a picturesque waterfront bustling with yachts, and a skyline dominated by the distinguished architecture of the U.S. Naval Academy, established in 1845.

In Annapolis, visitors can explore the residence of a Founding Father, take the helm of a schooner, and witness the site where Kunta Kinte first arrived on American soil as an enslaved individual in 1767.

1. Colonial Annapolis Historic District

The first aspect that catches your attention while exploring the historic downtown area is the absence of a conventional grid system.

At the dawn of the 18th century, Annapolis was designed by the Governor of Maryland, Francis Nicholson (1655-1727), as a Baroque planned city featuring grand circles with radiating streets.

One of these circles contains the Maryland State House, while another encompasses St. Anne’s Church (1692).

A robust economy, fueled by shipping and agriculture, led to the establishment of institutions of higher education, arts, sports (notably horse racing), and opulent mansions that later hosted Founding Fathers.

Annapolis is home to more original 18th-century Georgian architecture than any other city in the nation, and we will discuss two notable residences that are open for public tours later in this article.

2. Annapolis City Dock

Bordered by historic storefronts, the brick-paved Main Street slopes down from St. Anne’s Church to where Annapolis meets the waters of the Chesapeake Bay.

Both Main Street and the adjacent Dock Street offer ideal settings for leisurely strolls on a summer day, teeming with pubs, inns, restaurants, galleries, and charming boutiques.

The area is dominated by small, independent businesses and craftsmanship that have thrived for 350 years. Numerous waterfront eateries feature outdoor seating, allowing diners to observe sleek yachts gliding past in Ego Alley.

City Dock serves as a backdrop for numerous annual events in Annapolis, from boat shows to Fourth of July celebrations and the Military Bowl Parade in December.

3. Maryland State House

Situated prominently in the State Circle, the Maryland State House (1772-1797) holds the distinction of being the oldest state capitol in the nation in continuous legislative operation and the only one that has served as the nation’s capitol (1783-1784).

The wooden dome, featured on the Maryland state quarter, is the largest in the United States constructed without the use of nails.

This dignified Georgian structure welcomes visitors daily during regular hours. Notably, it was in the Old Senate Chamber that George Washington resigned his commission as commander-in-chief in 1783, and the Treaty of Paris was ratified, signifying the official conclusion of the Revolutionary War.

Exhibits commemorate this significant event, along with several monuments honoring key figures such as Harriet Tubman (1822-1913) and Frederick Douglass (1818-1895).

4. U.S. Naval Academy

Adjacent to the Colonial Annapolis Historic District, the U.S. Naval Academy has been an integral part of the city for nearly 180 years.

Reservations are not necessary for a guided 90-minute tour of this solemn campus.

Coordinated by the Armel-Leftwich Visitor Center, these tours occur multiple times daily, highlighting the academy’s numerous architectural and historical landmarks.

The optimal time to visit is just before noon to witness the impressive sight of thousands of Midshipmen marching into Tecumseh Court, framed by the magnificent Beaux-Arts Bancroft Hall, a tradition dating back to 1905.

The Naval Academy Chapel, established in 1908, is an unforgettable highlight of the tour, containing the remains of John Paul Jones (1747-1792), the Father of the American Navy, in its crypt.

5. U.S. Naval Academy Museum

Preble Hall at the U.S. Naval Academy serves as a primary destination for visitors, housing the U.S. Naval Academy Museum.

This institution features two floors of exhibits, blending interactivity, video, and audio displays with an array of compelling artifacts.

Visitors can explore the historical significance of naval power, the evolution of the U.S. Navy, and the academy’s legacy of training capable leaders.

The museum holds an impressive collection of medals, weapons, uniforms, flags, navigation instruments, model ships, books, photographs, and approximately 1,200 paintings.

A noteworthy exhibit includes selections from a collection of over 20 ship models crafted from bone by French prisoners of war during the Napoleonic Wars.

6. William Paca House

Several of the exquisite residences in the Colonial Annapolis Historic District welcome visitors and merit exploration.

One of substantial historical importance is the home of lawyer William Paca (1740-1799), a signatory of the Declaration of Independence.

Paca contributed significantly to the design of the house, which has largely been restored to its original mid-1760s appearance.

Guided tours depart hourly on the half-hour, providing insight into expertly preserved rooms, including the parlor, grand foyer, kitchen, and various bedrooms while detailing the lives of the residents, including family members, staff, and enslaved individuals.

Admission includes a self-guided tour of the magnificent two-acre walled garden, featuring a charming summerhouse.

7. Banneker-Douglass Museum

An essential stop in the Colonial Annapolis Historic District is this museum that chronicles Maryland’s African American heritage.

Housed in the historic Gothic Revival Mt. Moriah African Methodist Episcopal Church, built in 1876 and renovated to its current form in 1896, this site served as the meeting hall for the First African Methodist Episcopal Church for nearly a century.

The museum’s permanent exhibit, Deep Roots, Rising Waters: A Celebration of African Americans in Maryland, spans from 1633 to the present.

Visitors learn about Maryland’s first African American settler, explore correspondence between almanac author Benjamin Banneker and Thomas Jefferson, hear an anti-slavery speech by reformer Frederick Douglass, and discover Thurgood Marshall’s efforts to transform the U.S. education system.

Additionally, there are always engaging temporary exhibits and events such as panel discussions, workshops, unveilings, and celebratory anniversaries.

8. Kunta Kinte – Alex Haley Memorial

At City Dock, visitors are reminded of Annapolis’s crucial role in the Atlantic slave trade during the 18th century.

Pulitzer Prize-winning author Alex Haley (1921-1992) recounted a profoundly emotional moment in his life occurring in 1967 when he stood at the site where his ancestor, Kunta Kinte, first arrived in the New World as an enslaved person 200 years prior.

A poignant memorial has been established here, depicting Haley reading to a diverse group of children.

The memorial also features the Story Wall, which includes ten plaques along the dock, each displaying excerpts from Roots, which chronicles Haley’s family history.

Adjacent to Market House is the Compass Rose, a world map inlaid with colorful granite and a bronze centerpiece.

This 14-foot diameter feature, with Annapolis at its center, serves as a reminder of the compasses utilized by sailors for centuries.

9. Chesapeake Blue Crab

The Chesapeake Bay is renowned for its blue crab, the state crustacean of Maryland and its most significant fishery.

Recent estimates indicate approximately 282 million blue crabs inhabit the bay, with about 160 million having reached maturity.

This region contributes over a third of the nation’s annual blue crab catch, representing an industry valued in the tens of millions of dollars.

Cracking open steamed or boiled crabs is a quintessential experience at the seafood restaurants in Annapolis, many of which provide tutorials for newcomers. Additionally, specialties such as Maryland crab dip, crab cakes, soft-shell crab, and Maryland crab soup are must-tries.

Notable dining establishments include Cantler’s Riverside Inn (458 Forest Beach Rd), Boatyard Bar & Grill (400 Fourth St), Carroll’s Creek Cafe (410 Severn Ave), and O’Learys Seafood Restaurant (310 Third St).

10. Quiet Waters Park

On the serene banks of the South River, approximately ten minutes south of downtown Annapolis, you will find a scenic 340-acre park boasting stunning waterfront views.

Quiet Waters Park is situated where Harness Creek flows into the river, featuring a dock on its west side where canoes, kayaks, paddleboards, rowboats, pedal boats, and bicycles can be rented.

Beyond the water, the park encompasses six miles of trails, including a beautiful promenade and scenic overlook.

Winter brings an ice rink with skate rentals available for a nominal fee, while summer showcases a beloved concert series with performances held on Saturdays.

The southern section of Quiet Waters Park includes a dog park, providing canines with their own beach to enjoy.

11. Navy Midshipmen Football

During the fall, Annapolis becomes engulfed in the enthusiasm of the college football season, with the city’s population swelling significantly for each home game at the Naval Academy.

The Midshipmen compete at the Navy-Marine Corps Memorial Stadium, which accommodates 34,000 spectators and is located on the grounds of the United States Naval Academy.

The highlight of the era undoubtedly came during Heisman winner Roger Staubach’s tenure in the early 1960s, though Coach Ken Niumatalolo has led a successful program since 2008.

While stadium seating is typically available, visitors can also relax on the grassy bank at the north end zone and should plan to arrive early for the traditional flyovers.

12. Sandy Point State Park

Located at the western end of the iconic Chesapeake Bay Bridge, Sandy Point State Park covers 786 acres of waterfront, famous for its well-liked beach.

Situated merely ten minutes from the historic center of Annapolis, the park allows visitors to appreciate the breathtaking scenery of the Chesapeake Bay, framed by the matching bridge, which was a trailblazer when it opened in the 1950s.

An intriguing landmark visible from the park is the Sandy Point Shoal Lighthouse, which stands 1,000 feet offshore, characterized by its Empire-style architecture with a beacon resting atop a mansard roof.

The sandy swimming beach spans a mile, with options to rent beach chairs and umbrellas. A marina featuring 22 launching ramps typically offers rentals for kayaks, paddleboards, and motorboats.

13. Schooner Woodwind

No visit to America’s Sailing Capital would be complete without venturing out into the bay with the wind in your hair.

The simplest option is to embark on one of the two 74-foot schooners, Woodwind and Woodwind II. During this experience, you have the opportunity to steer the boat, assist with raising the sails, or sit back and enjoy the stunning views.

Departing from the historic waterfront, the cruise will take you past the Naval Academy and into the bay as far as the Chesapeake Bay Bridge.

Accompanied by a knowledgeable guide, you will learn about the local ecology, sailing intricacies, and the history of Annapolis throughout your journey.

14. Hammond-Harwood House

Among the finest surviving Colonial mansions in the United States, the Hammond-Harwood House in Annapolis is open as a historic house museum.

This National Historic Landmark, designed by architect William Buckland (1734-1774), offers a distinctive design directly inspired by a plate in Andrea Palladio’s The Four Books of Architecture (1570).

Visitors can admire the building’s elegant proportions, formal rooms, intricately carved main entrance, gardens, and a rich collection of paintings, furniture, and decorative arts.

There is also a wealth of history to uncover, including the narratives of the enslaved individuals who resided in the house, as well as the lives of the Hammond and Chase families. Throughout the year, the museum hosts regular special tours, lectures, concerts, and family-oriented programs.

15. United States Sailboat Show

Each October, one of the largest and most prestigious in-water boat shows globally takes place across the extensive docks in downtown Annapolis.

This multi-day event attracts over 50,000 boating enthusiasts from around the world, who can board and inspect hundreds of vessels from prominent sailboat manufacturers.

This unique opportunity allows prospective buyers to make direct comparisons of the latest sailboats. Alongside the water, a complex of tents hosts vendors showcasing the newest accessories, gear, clothing, and electronics.

Attendees can enjoy drink tastings, engage with industry professionals, participate in educational programs, and network with fellow boating aficionados.