23 Best & Fun Things To Do in Annapolis (MD)

Annapolis, Maryland, is a charming city located along the shores of the Chesapeake Bay. The city is known as “America’s Sailing Capital.” It offers picturesque views of the waterfront, creating a vibrant, maritime atmosphere.

Annapolis is the capital of Maryland, with a population of around 40,000. The city sits near Baltimore and Washington, DC, making it easily accessible for visitors and locals alike.

One of Annapolis’s most iconic landmarks is the United States Naval Academy, which attracts many tourists and holds a prominent place in the city’s history. Historic charm defines Annapolis with its cobblestone streets, colonial buildings, and the Maryland State House, the oldest state capitol still in use.

Surrounded by the Severn River and Spa Creek, Annapolis enjoys scenic water views and access to various waterfront activities. The city’s nickname reflects its strong connection to boating and water sports. Downtown, you’ll find City Dock and Ego Alley, popular gathering spots where locals and visitors watch boats sail by.

Annapolis’s lively arts district, rich history, and waterfront views make it unique. The city is known for its festivals, including the Military Bowl and Annapolis Baygrass Festival, which highlight its community spirit. Annapolis’s blend of history, maritime culture, and local charm make it a memorable place on the Chesapeake Bay.

Are you planning to visit Annapolis? Here are the best things to do in Annapolis, MD.

Things To Do in Annapolis, MD

1. Check out the Annapolis Maritime Museum & Park

The Annapolis Maritime Museum & Park is a must for anyone curious about the Chesapeake Bay’s maritime heritage. The museum focuses on the history and ecology of the Bay, offering insights into Annapolis’s connection to the sea. Visitors can explore exhibits on oyster harvesting, the life of watermen, and the Bay’s unique ecosystems.

A highlight is the historic McNasby Oyster Company building, which houses various artifacts and interactive displays. Through hands-on exhibits, you can learn how oysters were once harvested and understand their crucial role in maintaining the Bay’s ecosystem. The museum also runs educational programs, guided tours, and even boating excursions for a more immersive experience.

In addition, the park side offers waterfront trails and outdoor exhibits. The museum frequently hosts community events, like outdoor concerts and environmental talks, making it a lively and informative spot to visit. 

Address: 723 Second St, Annapolis, MD 21403

2. Explore Historic Annapolis Museum & Store

The Historic Annapolis Museum & Store offers a fascinating journey into Annapolis’s colonial past. This museum delves into the history of the city from its early days in the 17th century through the American Revolution. The museum includes interactive exhibits, detailed displays, and artifacts that highlight the lives of Maryland’s early settlers, Native American culture, and the development of Annapolis.

A standout exhibit is “Freedom Bound,” which tells stories of enslaved people who sought freedom in Maryland. The museum’s small, carefully curated displays make it easy to engage with local history. Visitors often find the historical storytelling here both emotional and informative, as it captures the struggles and resilience of various communities throughout Annapolis’s history.

After exploring the museum, visit the store for unique souvenirs, including books on local history, handmade crafts, and nautical gifts. This museum is ideal for families and anyone interested in learning about Annapolis’s role in American history.

Address: 99 Main St, Annapolis, MD 21401

3. Stroll around City Dock and Ego Alley

City Dock is the lively heart of Annapolis. This waterfront area offers a charming mix of shops, restaurants, and stunning views of the Chesapeake Bay. Ego Alley, a narrow waterway where boaters come to show off their vessels, is a favorite spot for people-watching. You’ll often see a mix of sailboats, yachts, and even kayaks moving slowly through, with spectators watching from the dock.

The area’s vibe is festive and welcoming, especially in the warmer months. You can grab a coffee from a nearby cafe, sit along the water’s edge, and enjoy the bustling atmosphere. City Dock also hosts several seasonal events, like the annual Boat Show and various holiday markets, making it a year-round destination for both locals and visitors.

Nearby, you can explore small boutiques and eateries offering seafood dishes, capturing the true flavor of Annapolis. City Dock is a great place to take in the spirit of this historic port city, surrounded by local charm and the beauty of the bay.

Address: Dock St, Annapolis, MD 21401

4. Tour the Maryland State House

The Maryland State House, built in 1772, is a historic treasure in Annapolis. It’s the oldest state capitol in continuous legislative use, with an incredible history tied to American independence. This iconic building once served as the temporary US Capitol from 1783 to 1784. It was here that the Treaty of Paris was ratified, officially ending the Revolutionary War.

Visitors can tour the State House and see its beautifully restored chambers, including the Old Senate Chamber where George Washington resigned as commander-in-chief of the Continental Army. The building itself is an architectural marvel with a large wooden dome, the only one of its kind in the country. Informational panels throughout help explain the rich history and significant events that happened here.

The State House is open to the public every day, and admission is free. It’s an insightful stop for history buffs and casual tourists alike, as it offers a unique glimpse into Maryland’s and America’s past. Don’t miss the impressive statue of Thurgood Marshall on the grounds, a tribute to Maryland’s role in civil rights.

Address: 100 State Cir, Annapolis, MD 21401

5. Discover the Banneker-Douglass Museum

The Banneker-Douglass Museum is Maryland’s official museum of African American heritage. The museum is named after the scientist Benjamin Banneker and abolitionist Frederick Douglass. It honors the contributions and history of African Americans in Maryland. The museum’s exhibits cover a range of topics from the Civil Rights Movement to contemporary African American culture.

The museum’s permanent exhibit, “Deep Roots, Rising Waters,” gives visitors a thorough look into Maryland’s African American history, with stories and artifacts that highlight struggles, resilience, and achievements. Temporary exhibits rotate frequently, often showcasing local artists and unique stories.

One of the most inspiring exhibits features photos and memorabilia from Maryland’s civil rights activists, including photos from the 1963 March on Washington. The museum offers guided tours, and its small size makes it easy to explore in an hour. Admission is free, making it a must-visit for anyone wanting to understand the depth of Maryland’s history.

Address: 84 Franklin St, Annapolis, MD 21401

6. Walk along Main Street’s Shops and Cafes

Main Street in Annapolis is a lively strip filled with shops, cafes, and restaurants that capture the city’s charm. As you stroll down this historic street, you’ll find an eclectic mix of boutiques, from vintage shops to modern stores selling nautical-themed gifts and local art. It’s the perfect place to pick up a souvenir, try local treats, or just enjoy the atmosphere.

There are plenty of cafes to stop at for a coffee break or a quick snack. Local favorites include Kilwins, known for their homemade ice cream, and Annapolis Ice Cream Company, where you can indulge in rich flavors. If you’re looking for something tasty, many restaurants offer fresh seafood, showcasing Maryland’s famous crab dishes.

Main Street leads directly to City Dock, so it’s easy to combine your shopping with a waterfront walk. The street is particularly charming in the evenings, with lights illuminating the historic buildings. .

Address: Main St, Annapolis, MD 21401

7. Visit St. Anne’s Episcopal Church

St. Anne’s Episcopal Church is one of Annapolis’s historic gems, standing as a symbol of resilience and community since 1692. The charming church is the third building on the site, as previous structures were destroyed by fire. The current structure, built in 1858, showcases beautiful Gothic Revival architecture and striking stained-glass windows.

Inside, the church feels warm and inviting, with intricate woodwork and a peaceful atmosphere. Visitors will notice the magnificent Tiffany stained-glass windows, a testament to the artistic craftsmanship of the time. St. Anne’s also houses a rare, 1739 Bell, originally imported from England, that rings out every Sunday morning, echoing through the historic district.

The churchyard is a serene spot to stroll, dotted with historic gravestones that date back centuries. St. Anne’s frequently hosts community events, including musical performances and seasonal services, making it a lively yet sacred part of Annapolis. 

Address: 199 Duke of Gloucester St, Annapolis, MD 21401

8. Tour the Hammond-Harwood House

The Hammond-Harwood House, built in 1774, is an architectural masterpiece and a must-visit for history and design enthusiasts. This historic home is one of the finest examples of colonial architecture in America. The house was designed by renowned architect William Buckland. It features elegant Georgian-style details, from symmetrical facades to intricate wood carvings.

Inside, the Hammond-Harwood House is a living museum filled with antique furniture, family portraits, and decorative arts from the 18th century. One of the highlights is the impressive dining room, which transports visitors back to colonial times with its period furnishings and table settings. Guided tours delve into the lives of the home’s early occupants, offering stories about colonial society and the challenges of the era.

The garden, located behind the house, adds to the charm, providing a tranquil space with seasonal blooms. Tours are offered regularly, allowing visitors to step back into the lifestyle of Annapolis’s colonial elite. It’s an insightful and beautifully preserved piece of history, perfect for anyone interested in early American life.

Address: 19 Maryland Ave, Annapolis, MD 21401

9. Relax at Quiet Waters Park

Quiet Waters Park, spanning over 340 acres, offers something for everyone, from scenic walking trails to art exhibits and picnic spots. It’s a favorite among locals and visitors looking to enjoy the outdoors in a peaceful setting. The park is known for its beautiful waterfront views along the South River, where you can spot boaters and kayakers on a sunny day.

The park has six miles of trails, perfect for walking, jogging, or biking, winding through forests and fields. One of the highlights is the Quiet Waters Dog Beach, where dogs can run free and splash in the water, making it a fun spot for pet owners.

In addition to nature, Quiet Waters Park hosts art shows in its galleries, showcasing local artists and adding a cultural touch to the experience. Quiet Waters is also a popular spot for events and weddings, with its charming gazebo and stunning natural backdrop. 

Address: 600 Quiet Waters Park Rd, Annapolis, MD 21403

10. Visit the United States Naval Academy

The United States Naval Academy in Annapolis is a must-visit for history enthusiasts and those interested in the military. This academy, founded in 1845, has trained some of the nation’s most distinguished naval officers. Visitors can explore the beautiful grounds and see historic buildings like Bancroft Hall and the Naval Chapel.

One of the highlights is the USNA Museum, which showcases exhibits on the Navy’s history, including impressive ship models and naval artifacts. The academy grounds also provide scenic views of the Severn River, and you might even see midshipmen (students) in their uniforms heading to classes or drills. Guided tours are available, offering insights into the academy’s traditions, values, and student life.

To enter, remember to bring identification, as it’s an active military facility. Check for updated visitor guidelines on the academy’s website, as security requirements can vary. 

Address: 121 Blake Rd, Annapolis, MD 21402

11. Explore the William Paca House & Garden

The William Paca House & Garden offers a step back into colonial Annapolis. This Georgian mansion, built in the 1760s, belonged to William Paca, a signer of the Declaration of Independence. Today, the house is a National Historic Landmark, restored to showcase the elegant lifestyle of the colonial elite.

Inside, the house is filled with period furnishings, decorative arts, and portraits that illustrate 18th-century life. Guided tours reveal stories about Paca’s life and the home’s architectural features, including beautifully carved woodwork and original details. Each room provides a snapshot of the daily lives of its original inhabitants, making it both educational and engaging.

The gardens are equally impressive, featuring terraced landscapes, flowering trees, and a charming summerhouse. Carefully reconstructed, these gardens offer a tranquil space for strolling and enjoying seasonal blooms. The Paca House & Garden is a favorite for history lovers, architecture fans, and garden enthusiasts alike, bringing colonial Annapolis to life in a beautifully preserved setting.

Address: 186 Prince George St, Annapolis, MD 21401

12. Take a Boat Tour on the Chesapeake Bay

A boat tour on the Chesapeake Bay is one of the best ways to experience Annapolis. These tours provide a scenic journey along the water, showcasing panoramic views of the city’s skyline, the US Naval Academy, and historic waterfront homes. Several companies offer boat tours, with ranging options from guided history cruises to sunset sails.

Popular choices include sightseeing cruises that offer live narration, sharing details about Annapolis’s maritime history and landmarks. For a romantic evening, opt for a sunset or dinner cruise, where you can enjoy a meal with a view. There are also specialty cruises, like themed pirate adventures for families with young kids.

Being on the water gives you a fresh perspective of Annapolis, away from the busy streets. Boat tours are available year-round, but the best time to go is during spring or fall when the weather is mild and the scenery is vibrant. It’s an experience that truly captures the spirit of Annapolis as a historic port city.

Address: Various departure points; main docks near City Dock, Annapolis, MD

13. Enjoy the Kunta Kinte-Alex Haley Memorial

The Kunta Kinte-Alex Haley Memorial is a powerful tribute located at Annapolis’s City Dock. This site commemorates the arrival of Kunta Kinte, an enslaved African ancestor of author Alex Haley. In Haley’s famous book, Roots , Kunta Kinte’s story is central to understanding the African American experience. The memorial is both a place of reflection and education, celebrating resilience, family, and freedom.

The memorial features a striking bronze statue of Alex Haley reading to a group of children, symbolizing the transmission of stories across generations. Surrounding the statue are plaques with inscriptions that highlight the experiences and challenges faced by African Americans. Each plaque adds depth to the story, providing a reflective space for visitors to learn and honor this legacy.

Events and gatherings often take place at the memorial, making it a vibrant yet solemn spot in the city. Visiting the memorial is a meaningful way to understand Annapolis’s history and pay tribute to those who endured hardship and ultimately triumphed. It’s a place that resonates deeply with visitors, fostering understanding and respect.

Address: City Dock, Annapolis, MD 21401

14. Watch a Show at Maryland Hall for the Creative Arts

Maryland Hall for the Creative Arts is Annapolis’s cultural hub, offering a rich lineup of performances, art exhibits, and workshops. Maryland Hall, which was originally a high school, was transformed into an arts center in 1979. It now hosts everything from ballet and theater to live concerts and art exhibitions, making it the perfect spot for an evening out.

The venue has a classic charm, with intimate performance spaces that create a close connection between artists and audiences. The Hall is home to the Annapolis Symphony Orchestra and Ballet Theater of Maryland, both of which regularly perform here. Visitors can enjoy a variety of genres, from classical music to modern dance, depending on the season.

Beyond performances, Maryland Hall also features galleries showcasing local and national artists. Art lovers can stroll through these exhibitions, which change throughout the year. Classes and workshops are also available, so visitors can dive into their creative side. 

Address: 801 Chase St, Annapolis, MD 21401

15. Walk the Arts District on West Street

The Arts District on West Street is Annapolis’s creative core, brimming with galleries, murals, and vibrant public art. This lively area is perfect for an afternoon stroll, with art studios, boutiques, and eateries lining the street. As you walk, you’ll encounter colorful murals and sculptures that give the neighborhood a unique and artistic vibe.

One of the district’s highlights is the First Sunday Arts Festival, held from May through November. During this monthly event, West Street transforms into an open-air market with local artists, craftspeople, and live performers. It’s a fun way to explore Annapolis’s creative scene and pick up one-of-a-kind pieces from local makers.

The Arts District also boasts a range of restaurants and cafes, perfect for grabbing a bite between gallery visits. The atmosphere here is eclectic and welcoming, drawing in artists, musicians, and visitors alike. Whether you’re a fan of visual art or just love discovering new, creative spaces, the West Street Arts District is a must-visit.

Address: West Street, Annapolis, MD 21401

16. Attend the Annapolis Boat Shows

The Annapolis Boat Shows, held twice a year in spring and fall, are among the largest in the United States. The US Powerboat Show and the US Sailboat Show attract thousands of attendees from all over the world, filling Annapolis’s City Dock with the latest in boating technology, impressive yachts, and sleek sailboats.

At these events, you can tour the boats on display, from luxurious yachts to smaller, versatile vessels. Many vendors showcase boating accessories, nautical apparel, and marine equipment, making it an exciting experience for anyone interested in maritime culture. You don’t need to be an expert sailor to enjoy the shows; Even newcomers find it fascinating to see the variety of boats and equipment.

The Annapolis Boat Shows are a great way to experience the city’s vibrant maritime culture. The shows often feature seminars, demonstrations, and even opportunities to try out boats on the water. It’s a festive, bustling environment where you can soak in the maritime spirit of Annapolis.

Address: City Dock, Annapolis, MD 21401

17. Discover Sandy Point State Park

Sandy Point State Park is the perfect spot for outdoor enthusiasts and families looking for a day of sun, sand, and nature. The park offers stunning views of the Bay Bridge and an array of activities for visitors. The sandy beach is ideal for swimming, picnicking, or simply lounging by the water.

Beyond the beach, Sandy Point State Park has a network of scenic trails that lead through woodlands and along the shore. Fishing enthusiasts can cast a line from the beach or designated fishing areas. The park also offers a boat launch for those who want to get out on the bay. Wildlife enthusiasts often spot herons, ospreys, and other birds native to the Chesapeake Bay area.

The park is open year-round and offers picnic pavilions, grills, and playgrounds, making it a family-friendly destination. In the winter months, the park hosts the popular Polar Bear Plunge, a charity event where brave souls dive into the chilly bay waters. Sandy Point provides a wonderful escape into nature, just minutes from downtown Annapolis.

Address: 1100 E College Pkwy, Annapolis, MD 21409

18. Enjoy a Picnic at Truxtun Park

Truxtun Park is a hidden gem in Annapolis, offering a peaceful retreat from the city’s hustle and bustle. This spacious park is perfect for a picnic, with plenty of open areas and shaded spots to spread out a blanket. Located along Spa Creek, Truxtun Park provides beautiful water views and an inviting, relaxed atmosphere.

In addition to picnic areas, the park has a variety of recreational facilities, including tennis courts, ball fields, and a skate park. The Truxtun Park Pool is a popular spot in the summer, where families can cool off and enjoy the outdoor pool area. There’s also a boat ramp for launching kayaks and canoes, allowing visitors to explore Spa Creek from the water.

One of the highlights of Truxtun Park is its network of walking trails, which meander through the woods and along the creek. It’s an ideal setting for a leisurely stroll or a scenic jog. Truxtun Park is a favorite among locals for its tranquil setting, making it a great spot for a family outing or a quiet afternoon picnic.

Address: 273 Hilltop Ln, Annapolis, MD 21403

19. Visit Thomas Point Shoal Lighthouse

Thomas Point Shoal Lighthouse, built in 1875, is one of the most iconic landmarks in Annapolis. This historic lighthouse stands proudly in the Chesapeake Bay, about a mile offshore. It’s the last remaining screw-pile lighthouse still in its original location and is a beloved symbol of Maryland’s maritime heritage. Listed as a National Historic Landmark, the lighthouse has been beautifully preserved to reflect its storied past.

The only way to visit Thomas Point Shoal is by boat, with tours departing regularly during the summer months. These guided tours offer an exciting experience, as you’ll get to learn about the lighthouse’s history, architecture, and the role it played in guiding ships safely through the bay. The interior of the lighthouse has been restored to look as it did in the late 19th century, complete with period furnishings and equipment.

A visit to Thomas Point Shoal Lighthouse provides a unique glimpse into the life of 19th-century lighthouse keepers and the Chesapeake’s rich maritime history. It’s a must-see for lighthouse enthusiasts and anyone interested in Maryland’s nautical past.

Address: Accessible by boat; tours depart from Annapolis Maritime Museum

20. Explore Historic London Town and Gardens

Historic London Town and Gardens, located on the South River, offers a fascinating look at early colonial life in Maryland. London Town was once a bustling 18th-century port town, and today, the site features reconstructed colonial buildings, archaeological ruins, and immersive exhibits that transport visitors back in time.

The William Brown House, a grand Georgian mansion built in the 1760s, is one of the site’s highlights. As you explore the house and grounds, you’ll learn about the lives of colonial settlers and the role London Town played as a center for trade and commerce. The gardens are equally enchanting, with native plants, flowering trees, and scenic river views that create a peaceful retreat.

Throughout the year, London Town hosts events like colonial reenactments, historical demonstrations, and seasonal festivals. With its blend of history, beautiful landscapes, and engaging programs, Historic London Town and Gardens offers a memorable experience for visitors of all ages.

Address: 839 Londontown Rd, Edgewater, MD 21037

21. Catch a Game at Navy-Marine Corps Memorial Stadium

The Navy-Marine Corps Memorial Stadium is an exciting destination for sports fans and anyone who enjoys a lively atmosphere. It is home to the US Naval Academy’s football team, the Navy Midshipmen. The stadium is the place to be on game day in Annapolis. With a capacity of over 34,000 seats, the stadium comes alive with cheers, music, and a strong sense of camaraderie.

Watching a Navy game here is a unique experience, filled with military traditions and pride. Before each game, fans can witness the impressive March-On by the Brigade of Midshipmen, as well as a flyover from Navy jets. The energy is electric, and fans of all ages enjoy the spirited atmosphere and strong support for the Midshipmen.

Beyond football, the stadium also hosts lacrosse games, concerts, and special events throughout the year. Its location near downtown Annapolis makes it easy to combine a visit to the stadium with exploring the city. For an unforgettable taste of Annapolis sports culture, catching a game at Navy-Marine Corps Memorial Stadium is a top pick.

Address: 550 Taylor Ave, Annapolis, MD 21401

22. St. John’s College Campus Tour

St. John’s College, founded in 1696, is one of the oldest institutions of higher education in the United States. The college offers a beautiful, historic campus with buildings dating back to the 18th century. The college is renowned for its unique “Great Books” curriculum, which focuses on classic texts and emphasizes discussion-based learning. Strolling through the campus, visitors can enjoy a sense of history and academic tradition.

McDowell Hall, one of the main buildings on campus, is a highlight with its Georgian architecture and significance as an original part of the college. The college grounds also feature quaint gardens, shady walkways, and open spaces perfect for a leisurely exploration. During your visit, you may encounter students engaged in discussions, reflecting the school’s intellectual atmosphere.

St. John’s College hosts various cultural events throughout the year, including lectures, concerts, and the popular Annapolis Cup croquet match against the Naval Academy. Touring this campus provides a unique perspective on Annapolis’s rich educational heritage and offers a peaceful break in a historic setting.

Address: 60 College Ave, Annapolis, MD 21401

23. Walk the Scenic Annapolis Historic District

Walking through the Annapolis Historic District is like stepping back in time. This charming area is filled with colonial-era buildings, cobblestone streets, and a vibrant mix of shops, restaurants, and historic landmarks. As you explore, you’ll find beautifully preserved 18th-century architecture, including landmarks like the Maryland State House and historic homes along Prince George Street.

A must-see in the district is the William Paca House and Garden, a Georgian mansion that showcases the life of a colonial governor. Many of the historic homes are marked with plaques, offering a glimpse into their storied past. The district is also home to small boutiques, art galleries, and cafes where you can take a break and soak up the ambiance.

Guided walking tours are available for those who want to dive deeper into the history of Annapolis. These tours cover the city’s colonial roots, maritime heritage, and stories of prominent figures who shaped the nation. Strolling the Historic District is a delightful way to experience Annapolis’s unique charm, offering both history and lively local culture.

Address: Main Street and surrounding area, Annapolis, MD 21401

Final Thoughts

Annapolis, MD, offers a rich blend of history, waterfront beauty, and vibrant local culture, making it an unforgettable destination. Before visiting, remember that parking downtown can be limited, especially during peak seasons or major events, so consider using local garages or public transportation.

Annapolis is walkable, especially downtown, so bring comfortable shoes. Whether you’re visiting for its maritime charm, historical sites, or lively arts scene, Annapolis is sure to captivate you with its warm, welcoming spirit.