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50 Things to Do in Annapolis, Maryland (MD)

Annapolis, the capital of Maryland, is a city steeped in history and brimming with maritime charm. Nestled along the scenic Chesapeake Bay, it offers a harmonious blend of colonial heritage, vibrant arts, and nautical adventures. Whether you're a history buff, sailing enthusiast, or foodie, Annapolis promises an unforgettable experience for every visitor, and if you're seeking more activities nearby, there are plenty of things to do in Inner Harbor, Maryland (MD) that complement the city's rich culture.

From strolling through its well-preserved historic district to setting sail on the tranquil waters, Annapolis combines the charm of the past with the vibrancy of modern-day attractions.

Unique Facts About Annapolis

Historic Significance

Annapolis holds a special place in American history. It served as the temporary capital of the United States in 1783-1784, where the Treaty of Paris was ratified, officially ending the Revolutionary War. This historic city has witnessed numerous pivotal moments in the birth of the nation, and its historic landmarks continue to tell the stories of America's past, much like the charming things to do in Havre de Grace, Maryland (MD), which offers a rich blend of history and scenic beauty.

Maritime Heritage

Known as "America's Sailing Capital," Annapolis is home to a rich maritime heritage. The city hosts numerous sailing events throughout the year, with the United States Sailboat Show being one of the most iconic events. Visitors can immerse themselves in the city's sailing culture, whether they are seasoned sailors or curious novices.

Architectural Charm

Annapolis is also renowned for its well-preserved architecture. The Annapolis Historic District boasts the largest collection of 18th-century Georgian architecture in the United States. As you wander through the cobblestone streets, you'll be captivated by the stunning buildings and the picturesque backdrop they create, offering a unique window into America's colonial past. For those looking to explore more, consider discovering things to do in Berlin, Maryland (MD), where history and charm blend seamlessly.

Infographic - 50 Things to Do in Annapolis, Maryland (MD)

50 Things to Do in Annapolis, Maryland (MD)

Annapolis, the capital city of Maryland, is known for its rich history, stunning waterfront views, and vibrant cultural scene. Whether you're an adventure seeker, history buff, or just looking to relax by the water, Annapolis offers a variety of activities for all types of visitors. Below, we've rounded up some of the top things to do in Annapolis to ensure you make the most of your visit.

1. Tour the U.S. Naval Academy

Short Description of Activity:
The U.S. Naval Academy is one of the most prestigious military institutions in the United States, offering a rich history of naval training and education. Visitors can tour the campus, which includes stunning architecture, historic landmarks, and the impressive Naval Academy Museum.

Pros and Cons:
Pros:

  • Educational experience about the history of the U.S. Navy.

  • Beautiful architecture and scenic views.

  • Opportunity to see midshipmen in action.

Cons:

  • Tours may require advance booking, especially during peak seasons.

  • Restricted areas may limit the full experience.

Key Attractions and Events:

  • The iconic Chapel, home to the Naval Academy's religious services.

  • The Crypt of John Paul Jones, a revered naval figure.

  • The historic Macdonough Hall and Bancroft Hall.

2. Visit the Maryland State House

Short Description of Activity:
The Maryland State House is the oldest state house in continuous legislative use in the United States. Visitors can take guided tours to explore the rich history of Maryland's government and its role in shaping the nation.

Pros and Cons:
Pros:

  • Stunning Georgian architecture.

  • Insight into Maryland’s political and historical significance.

  • Free guided tours available.

Cons:

  • Limited accessibility due to ongoing legislative sessions.

  • Can get crowded during legislative sessions.

Key Attractions and Events:

  • The Old Senate Chamber, where George Washington resigned his commission as commander-in-chief.

  • The State Circle, surrounded by historic buildings.

3. Stroll the Annapolis Historic District

Short Description of Activity:
Annapolis’s Historic District is a charming area lined with cobblestone streets, colonial homes, and plenty of shops, cafes, and restaurants. Walking through the district provides a glimpse of Annapolis’s past and vibrant present.

Pros and Cons:
Pros:

  • Beautiful, picturesque streets perfect for photos.

  • Many unique shops and boutiques to explore.

  • Rich in history and architecture.

Cons:

  • Streets can be narrow and crowded during weekends.

  • Parking may be difficult to find in peak seasons.

Key Attractions and Events:

  • Colonial homes and buildings dating back to the 18th century.

  • The Annapolis City Dock, where you can watch the boats and enjoy local seafood.

4. Explore William Paca House & Garden

Short Description of Activity:
The William Paca House & Garden is a beautifully restored 18th-century Georgian mansion that offers a glimpse into the life of one of Maryland’s founding fathers. The house is surrounded by stunning gardens and provides an immersive historical experience.

Pros and Cons:
Pros:

  • Gorgeous, well-maintained gardens.

  • A glimpse into the lifestyle of a Maryland statesman.

  • A serene, peaceful location to visit.

Cons:

  • Tours are guided, which can limit the time spent in each area.

  • Admission fee may be considered steep for some visitors.

Key Attractions and Events:

  • The stunning formal gardens with historical plant species.

  • The house, which has been fully restored to its 18th-century grandeur.

5. Relax at Quiet Waters Park

Short Description of Activity:
Quiet Waters Park is a peaceful retreat with trails, wildlife, and art galleries. Located just outside the city, this park offers visitors a quiet and natural space to relax, walk, and enjoy outdoor activities.

Pros and Cons:
Pros:

  • Ideal for nature lovers and those seeking peace.

  • Beautiful walking trails and scenic landscapes.

  • Home to the Ann Arundel County Arts Council and art galleries.

Cons:

  • Limited activities during the colder months.

  • Not as well-known, so amenities may not be as developed.

Key Attractions and Events:

  • The Art Gallery, featuring local artists.

  • Beautiful trails for walking, hiking, or picnicking.

6. Eat at Chick & Ruth's Delly

Short Description of Activity:
Chick & Ruth's Delly is a local institution, famous for its hearty meals, including their legendary crab cakes and massive sandwiches. A visit here provides not just great food but an authentic Annapolis dining experience.

Pros and Cons:
Pros:

  • Home to some of the best crab cakes in the area.

  • A nostalgic, old-school deli atmosphere.

  • Excellent value for the portion sizes.

Cons:

  • Can get busy, especially during lunch and dinner hours.

  • Service may feel rushed due to the high volume of customers.

Key Attractions and Events:

  • The famous Crab Cake Sandwich.

  • The atmosphere, filled with locals and tourists alike.

7. Walk Along Ego Alley

Short Description of Activity:
Ego Alley is a small, scenic waterway located at the Annapolis City Dock, where visitors can stroll along and watch luxury yachts, boats, and sailors. It’s a great place to relax, enjoy the view, and soak in the Annapolis waterfront atmosphere.

Pros and Cons:
Pros:

  • Excellent spot for people-watching and boat-spotting.

  • Beautiful views of the Annapolis harbor.

  • Close to cafes and shops along the dock.

Cons:

  • Can get crowded, especially during weekends and events.

  • Limited activities aside from walking.

Key Attractions and Events:

  • The chance to see beautiful yachts and boats docking.

  • Local restaurants and bars where you can grab a bite after your stroll.

8. Attend the U.S. Sailboat Show

Short Description of Activity:
Held annually, the U.S. Sailboat Show in Annapolis is one of the world’s largest and most prestigious events dedicated to sailing. Visitors can explore hundreds of sailboats, learn about the latest in nautical technology, and attend various seminars.

Pros and Cons:
Pros:

  • A must-visit for sailing enthusiasts.

  • Wide variety of boats to explore, from luxury yachts to smaller vessels.

  • Opportunities to meet industry professionals and attend seminars.

Cons:

  • High admission cost for non-exhibitors.

  • The event can be overwhelming with large crowds.

Key Attractions and Events:

  • The Sailboat Show, featuring hundreds of boats.

  • Seminars on sailing, navigation, and boat maintenance.

9. Sail on the Schooner Woodwind

Short Description of Activity:
A sailing experience on the Schooner Woodwind offers a unique way to see the Annapolis harbor and Chesapeake Bay. This 74-foot schooner is ideal for a romantic evening sail or a relaxing afternoon outing.

Pros and Cons:
Pros:

  • Stunning views of Annapolis from the water.

  • The sailboat is small, providing an intimate experience.

  • Educational tours about the local maritime culture.

Cons:

  • Can be weather-dependent, with some cancellations due to poor conditions.

  • Tickets can be pricey compared to other harbor tours.

Key Attractions and Events:

  • Sailing through the Annapolis Harbor and Chesapeake Bay.

  • The chance to experience a traditional sailing vessel.

10. Crack Crabs at Cantler’s Riverside Inn

Short Description of Activity:
Cantler’s Riverside Inn is a favorite local spot for seafood lovers, particularly known for its crabs. Visitors can enjoy cracking fresh Maryland blue crabs while overlooking the peaceful waters of the Rhode River.

Pros and Cons:
Pros:

  • One of the best places to try Maryland’s famous crabs.

  • A laid-back, authentic dining experience.

  • Scenic waterfront dining with great views.

Cons:

  • Can be expensive, especially during peak crab season.

  • The restaurant is small and may have long wait times.

Key Attractions and Events:

  • Freshly steamed blue crabs, a Maryland specialty.

  • Beautiful views of the Rhode River while enjoying a meal.

11. Take a Watermark Harbor Cruise

Short Description:
A Watermark Harbor Cruise is a fantastic way to experience Annapolis from the water. These cruises offer scenic views of the Chesapeake Bay, the U.S. Naval Academy, and the Annapolis Harbor.

Pros:

  • Stunning views of the waterfront and historic landmarks.

  • Comfortable, relaxing experience on the water.

  • Great for couples, families, and photographers.

Cons:

  • Dependent on weather conditions; cancellations can occur during bad weather.

  • Can be crowded during peak tourist seasons.

Key Attractions and Events:

  • Tours of the U.S. Naval Academy from the water.

  • Seasonal themed cruises, such as sunset or holiday cruises.

12. Visit Banneker-Douglass Museum

Short Description:
This museum highlights Maryland’s African American history and heritage. It features exhibitions and programs dedicated to the contributions of African Americans in the state.

Pros:

  • Rich in history and culture.

  • Offers educational insights into African American history.

  • Accessible and informative for all ages.

Cons:

  • Limited parking in the area.

  • Smaller museum compared to larger regional museums.

Key Attractions and Events:

  • Art exhibitions and historical displays.

  • Cultural events and educational programs.

13. Shop Local on Main Street

Short Description:
Annapolis' Main Street is lined with charming boutiques, galleries, and local shops, offering everything from unique gifts to fine clothing and artwork. It’s a great spot for strolling and shopping.

Pros:

  • Charming, historic atmosphere.

  • Supports local businesses.

  • Wide variety of shops, restaurants, and cafes.

Cons:

  • Can be busy, especially on weekends.

  • Parking can be tricky during peak shopping hours.

Key Attractions and Events:

  • Local art galleries showcasing regional artists.

  • Frequent farmers’ markets and seasonal fairs.

14. Tour Hammond-Harwood House

Short Description:
This historic house, built in the 18th century, is a prime example of colonial architecture and houses a collection of American art and furniture. It offers a glimpse into Annapolis' past.

Pros:

  • Historic architecture and beautiful gardens.

  • Fascinating history related to the early years of Annapolis.

  • Guided tours provide an in-depth experience.

Cons:

  • Limited accessibility for those with mobility issues.

  • Can take longer to explore if you're interested in all the details.

Key Attractions and Events:

  • Special historical events and themed tours.

  • Seasonal garden displays.

15. Explore Annapolis Maritime Museum

Short Description:
The Annapolis Maritime Museum focuses on the area's maritime history, highlighting its evolution from colonial trade to modern-day boating and fishing. The museum includes exhibits, a boatyard, and a waterfront park.

Pros:

  • Ideal for history lovers and maritime enthusiasts.

  • Hands-on exhibits that appeal to kids and families.

  • Offers insight into the local fishing and boat-building industries.

Cons:

  • Museum is somewhat small, so the visit may be brief.

  • Limited exhibits during the off-season.

Key Attractions and Events:

  • Educational programs for children and adults.

  • Annual Oyster Fest celebrating local seafood.

16. Watch a Show at Maryland Hall

Short Description:
Maryland Hall is Annapolis’ premier performing arts center, hosting a wide variety of performances including music, theater, and dance. It's a great place to catch a show while visiting the city.

Pros:

  • A variety of performances to suit all interests.

  • Impressive acoustics and theater design.

  • Offers performances from local and international artists.

Cons:

  • Tickets can be pricey for some shows.

  • Limited availability of certain performances during the off-season.

Key Attractions and Events:

  • Year-round performances, from classical concerts to contemporary dance.

  • Educational programs for local students and youth.

17. Swim at Sandy Point State Park

Short Description:
Sandy Point State Park is a popular destination for swimming, picnicking, and enjoying the outdoors. Located along the Chesapeake Bay, it offers beautiful views and a relaxing atmosphere.

Pros:

  • Great place for a day outdoors with family or friends.

  • Calm waters perfect for swimming.

  • Scenic views of the Bay Bridge.

Cons:

  • Can get crowded during summer weekends.

  • Limited shade, so visitors should come prepared for sun exposure.

Key Attractions and Events:

  • Annual beach events and picnics.

  • The chance to spot wildlife, including birds and marine life.

18. Visit Charles Carroll House

Short Description:
The Charles Carroll House is a historic home of one of Maryland’s signers of the Declaration of Independence. The house offers tours that explore the life of Charles Carroll and the early history of the country.

Pros:

  • Fascinating look at early American history.

  • Beautifully preserved historical home.

  • Peaceful and less crowded than other historical sites.

Cons:

  • Limited time for tours.

  • Not as interactive as other historical venues.

Key Attractions and Events:

  • Regular historical tours.

  • Special lectures on Maryland's colonial history.

19. Hang at Annapolis City Dock

Short Description:
The City Dock is the heart of Annapolis' waterfront and a popular spot for sightseeing, dining, and enjoying the beautiful harbor views. It’s also the location of many boat tours and waterfront events.

Pros:

  • Perfect for a relaxing walk along the water.

  • A variety of restaurants and shops nearby.

  • Beautiful views of the harbor and boats.

Cons:

  • Can be busy during peak tourist seasons.

  • Limited parking options nearby.

Key Attractions and Events:

  • Frequent sailing events and boat shows.

  • Live music performances during the summer.

20. Step into St. Anne’s Church

Short Description:
St. Anne’s Church is one of the oldest churches in Maryland and boasts a rich history, beautiful architecture, and peaceful grounds. It's an important cultural and religious landmark in Annapolis.

Pros:

  • Beautiful, historic architecture.

  • Quiet and serene atmosphere.

  • Ideal for history and architecture enthusiasts.

Cons:

  • Limited visitor hours for tours.

  • Not as interactive as some other sites in Annapolis.

Key Attractions and Events:

  • Regular religious services and special holiday events.

  • Historical walking tours available on request.

21. Attend the Annapolis Film Festival

Short description of activity
The Annapolis Film Festival is a celebration of independent films, attracting filmmakers and movie buffs from all over the world. The festival features screenings of diverse films, panel discussions, and interactive sessions with filmmakers.

Pros and Cons

  • Pros:

    • Great opportunity to watch unique, independent films not typically shown in mainstream theaters.

    • A chance to meet filmmakers and actors and attend Q&A sessions.

    • A fun and creative experience for film lovers and industry professionals alike.

  • Cons:

    • Tickets can sell out quickly, especially for popular screenings.

    • The festival is limited to a few days, so it’s a short-lived event.

Key attractions and events

  • Independent films from various genres.

  • Meet-and-greet events with filmmakers.

  • Q&A sessions and panel discussions with industry experts.

22. Walk the Colonial Annapolis District

Short description of activity
Walking through the Colonial Annapolis District feels like stepping back in time. The cobblestone streets, charming buildings, and historical landmarks make it a wonderful place to explore.

Pros and Cons

  • Pros:

    • Rich in history and culture, offering a step back into colonial America.

    • A great place for walking, taking photos, and learning about the nation's history.

  • Cons:

    • Some streets can be crowded, especially during peak tourist seasons.

    • Limited parking options for visitors.

Key attractions and events

  • Maryland State House.

  • St. Anne’s Church.

  • Historic buildings and museums.

23. See the Kunta Kinte-Alex Haley Memorial

Short description of activity
The Kunta Kinte-Alex Haley Memorial honors the story of Kunta Kinte, the African man who was enslaved and brought to America. It’s a moving tribute to the legacy of Kunta Kinte and author Alex Haley.

Pros and Cons

  • Pros:

    • Thought-provoking and educational, shedding light on the history of slavery and African-American heritage.

    • The memorial is beautifully designed with sculptures and plaques.

  • Cons:

    • It can be emotionally intense for some visitors.

    • May require a guided tour to fully appreciate its historical significance.

Key attractions and events

  • Sculptures depicting scenes from Alex Haley’s “Roots.”

  • Historical markers explaining the story of Kunta Kinte.

24. Ride the Annapolis Trolley Tour

Short description of activity
The Annapolis Trolley Tour is a guided sightseeing experience that takes visitors on a historical journey through the charming streets of Annapolis, showcasing its key landmarks and history.

Pros and Cons

  • Pros:

    • A great way to get an overview of the city’s history and attractions in a short time.

    • Comfortable and informative ride with a knowledgeable guide.

  • Cons:

    • The tour duration is relatively short, so you may not get to see everything in detail.

    • Limited availability during off-season months.

Key attractions and events

  • Historic Annapolis landmarks, including churches, homes, and government buildings.

  • Scenic views of the waterfront and parks.

25. Catch Live Music at Rams Head Tavern

Short description of activity
Rams Head Tavern is a popular venue for live music, offering an intimate setting where you can enjoy performances by both local artists and national acts.

Pros and Cons

  • Pros:

    • A great venue for music lovers with a diverse range of live performances.

    • The tavern offers a cozy and lively atmosphere, perfect for enjoying food and drinks while listening to live music.

  • Cons:

    • Can get crowded during popular performances, so it’s advisable to book in advance.

    • The venue can sometimes be noisy, making it hard to converse during the show.

Key attractions and events

  • Local and national live music performances.

  • Delicious pub food and craft beers.

  • Intimate setting with great acoustics.

26. Honor Justice at Thurgood Marshall Memorial

Short description of activity
The Thurgood Marshall Memorial honors the life and legacy of Thurgood Marshall, the first African-American Supreme Court Justice. It’s an inspiring site for anyone interested in civil rights and justice.

Pros and Cons

  • Pros:

    • A powerful tribute to one of the most influential figures in American civil rights history.

    • The memorial is located near other key historical landmarks, making it a great stop on a historical tour.

  • Cons:

    • The memorial may be small and not as grand as other memorials, but it holds deep historical significance.

    • Limited interactive elements for younger visitors.

Key attractions and events

  • Statue and historical plaques honoring Justice Thurgood Marshall.

  • Educational exhibits on civil rights and justice.

27. Browse the Annapolis Arts District

Short description of activity
The Annapolis Arts District is a vibrant area where you can enjoy local art galleries, theaters, and creative spaces. It’s an ideal place for art lovers to explore Annapolis’ creative scene.

Pros and Cons

  • Pros:

    • Great place to explore Annapolis’ thriving arts scene.

    • The district has a variety of galleries, shops, and theaters to visit.

  • Cons:

    • Some galleries may have limited hours or may not be open during certain seasons.

    • Can be busy during special events and art shows.

Key attractions and events

  • Local art galleries and studios.

  • Outdoor art installations and public art.

  • Theaters offering performances and community events.

28. Join Annapolis Pride Festival

Short description of activity
The Annapolis Pride Festival is a colorful celebration of the LGBTQ+ community, featuring parades, performances, and events that promote diversity and inclusion.

Pros and Cons

  • Pros:

    • A lively and fun event that celebrates diversity and inclusion.

    • Great for families, friends, and individuals to come together in support of the LGBTQ+ community.

  • Cons:

    • The festival can get crowded, especially during peak hours.

    • Parking can be difficult to find during the event.

Key attractions and events

  • Pride parade with vibrant floats and performers.

  • Live performances and music.

  • Vendors and food trucks offering a variety of goods.

29. Visit Anne Arundel County Farmers Market

Short description of activity
The Anne Arundel County Farmers Market is a local favorite for fresh produce, handmade goods, and unique culinary items. It’s a perfect stop for those wanting to experience the local flavors of Annapolis.

Pros and Cons

  • Pros:

    • Offers fresh, locally-grown produce and unique artisanal products.

    • A great place to support local farmers and artisans.

  • Cons:

    • The market may be busy, especially on weekends.

    • Limited selection in off-seasons.

Key attractions and events

  • Fresh fruits, vegetables, and handmade goods.

  • Local vendors selling homemade baked goods and crafts.

  • Live music performances.

30. Take the Kids to Chesapeake Children’s Museum

Short description of activity
The Chesapeake Children’s Museum is an interactive and educational space designed for young visitors. With hands-on exhibits and outdoor play areas, it’s a great place to bring children to learn and play.

Pros and Cons

  • Pros:

    • Educational and engaging for children, with many interactive exhibits.

    • Perfect for a family day out.

  • Cons:

    • It may not appeal to older children or adults as much.

    • Can be crowded during weekends and school holidays.

Key attractions and events

  • Hands-on exhibits related to Chesapeake Bay and the environment.

  • Outdoor play areas and nature trails.

  • Special events for children, including craft workshops and interactive programs.

31. Dress Up for the Maryland Renaissance Festival

Short Description of Activity
The Maryland Renaissance Festival is a must-visit event for anyone who loves medieval history, costumes, and fun. Held annually in Crownsville, just outside of Annapolis, this lively festival lets you step back in time to the 16th century. Expect jousting tournaments, falconry displays, musical performances, and a lot of people in elaborate costumes.

Pros

  • Great for families and kids.

  • Interactive performances and themed activities.

  • Vibrant atmosphere with food, drinks, and shopping.

Cons

  • Limited to a specific time of the year.

  • Can get crowded, especially on weekends.

  • Some events might be more expensive.

Key Attractions and Events

  • Jousting tournaments.

  • Live entertainment and street performers.

  • Craft vendors and artisans.

  • Themed food and drink stalls.

32. Tour the National Cryptologic Museum (Nearby)

Short Description of Activity
Located just a short drive from Annapolis, the National Cryptologic Museum is dedicated to the history of cryptology and the art of codebreaking. It’s a fascinating, family-friendly museum that offers interactive exhibits showcasing the role of cryptography in military intelligence, the Cold War, and beyond.

Pros

  • Free entry.

  • Great educational experience for all ages.

  • Interesting and unique exhibits.

Cons

  • Not much for younger children to engage with.

  • Limited interactive activities outside of exhibits.

Key Attractions and Events

  • Interactive displays on encryption and decryption.

  • History of American codebreaking efforts.

  • Special exhibits on famous codes and cryptographers.

33. Shop & Dine at Annapolis Towne Centre

Short Description of Activity
Annapolis Towne Centre is a modern shopping and dining destination in Annapolis, offering a mix of upscale boutiques, chain stores, and delicious eateries. It’s perfect for a leisurely afternoon of shopping, followed by a meal at one of the center's many restaurants.

Pros

  • Variety of shopping options.

  • Wide selection of dining experiences.

  • Relaxing, pleasant atmosphere with outdoor seating areas.

Cons

  • Can be crowded during weekends.

  • Limited options for those seeking unique, locally-owned stores.

Key Attractions and Events

  • Upscale retail shops.

  • Trendy cafes and restaurants.

  • Outdoor events during holidays and seasons.

34. Take a Historic Ghost Walk

Short Description of Activity
Annapolis is known for its rich history, and a ghost walk offers a thrilling way to explore the city's haunted past. Guides take you on an evening stroll through historic streets, telling eerie tales about the ghostly residents that are said to haunt the city.

Pros

  • Fun, spooky activity for the evening.

  • Engaging, informative guide with interesting historical anecdotes.

  • Great for history enthusiasts.

Cons

  • Not ideal for younger children.

  • Walking in the dark might not be suitable for all.

  • Weather can impact the experience.

Key Attractions and Events

  • Haunted walking tours through Annapolis' historic district.

  • Stories of Revolutionary War ghosts.

  • Dark, historic streets with eerie charm.

35. Explore the Chesapeake Bay Foundation’s Merrill Center

Short Description of Activity
The Chesapeake Bay Foundation’s Merrill Center offers a fantastic opportunity to learn about and protect the Chesapeake Bay ecosystem. Through interactive exhibits and beautiful nature trails, you can discover the bay’s vital role in the region’s environmental health.

Pros

  • Educational and interactive.

  • Beautiful nature trails for outdoor enthusiasts.

  • Focus on conservation and protecting the bay.

Cons

  • Limited indoor exhibits.

  • Can be a bit off the beaten path for tourists.

Key Attractions and Events

  • Environmental education programs.

  • Scenic nature trails.

  • Exhibits on the Chesapeake Bay's ecosystem.

36. Paddleboard or Kayak Spa Creek

Short Description of Activity
Spa Creek offers the perfect opportunity for kayaking or paddleboarding. With calm waters and stunning views of Annapolis, it’s a serene way to enjoy the outdoors and explore the city from a different perspective. You can rent equipment from local shops and enjoy a day on the water.

Pros

  • Calm and scenic waters ideal for beginners.

  • Affordable rental options.

  • Stunning views of Annapolis from the water.

Cons

  • Can be crowded during peak times.

  • Weather conditions can impact water sports.

Key Attractions and Events

  • Scenic water views of the city’s waterfront.

  • Opportunities for wildlife spotting.

  • Rentals available from local shops.

37. Book a Foodie Tour Around Downtown

Short Description of Activity
Annapolis is a foodie’s paradise, and a food tour around downtown is the perfect way to sample the best of what the city has to offer. From local seafood to mouthwatering desserts, you’ll visit several restaurants and eateries to try unique dishes while learning about Annapolis' culinary history.

Pros

  • Great way to explore Annapolis' food scene.

  • Knowledgeable guides provide local insights.

  • Wide variety of food choices, from seafood to local specialties.

Cons

  • The tour can be pricey.

  • Can be overwhelming if you don't like walking a lot.

Key Attractions and Events

  • Seafood delicacies, such as Maryland crab cakes.

  • Sweet stops for dessert lovers.

  • Local food and beverage pairings.

38. Relax with Coffee at Ceremony Coffee Roasters

Short Description of Activity
For coffee lovers, Ceremony Coffee Roasters is a must-visit in Annapolis. Known for its high-quality, ethically sourced coffee beans, this café offers a relaxing atmosphere where you can sip a rich cup of coffee and enjoy light bites.

Pros

  • Excellent coffee quality.

  • Cozy, quiet environment for relaxation.

  • Locally-owned business with a focus on sustainability.

Cons

  • Small seating area, can get crowded.

  • Higher-priced coffees compared to chains.

Key Attractions and Events

  • Specialty coffee drinks.

  • Seasonal beverages and light snacks.

  • Coffee education for enthusiasts.

39. Catch a Performance at Classic Theatre of Maryland

Short Description of Activity
If you’re a fan of live theatre, the Classic Theatre of Maryland offers an impressive lineup of productions throughout the year. The theatre showcases both classic plays and new works, providing excellent performances that add culture and entertainment to your Annapolis visit.

Pros

  • High-quality performances.

  • Comfortable, intimate setting.

  • Variety of plays throughout the year.

Cons

  • Limited showtimes and seating.

  • Ticket prices can be higher for popular shows.

Key Attractions and Events

  • Performances of both classic and contemporary works.

  • Comfortable and intimate theater.

  • Special seasonal events and performances.

40. Get a Tattoo at Lucky Bird Tattoo (Local Favorite!)

Short Description of Activity
Lucky Bird Tattoo is a local favorite for anyone looking to get a tattoo in Annapolis. Known for its talented artists and friendly atmosphere, this tattoo parlor provides a great spot to get a personalized piece of art that will serve as a lasting memory of your trip.

Pros

  • Skilled tattoo artists.

  • Friendly, welcoming atmosphere.

  • Custom tattoos tailored to your design.

Cons

  • Can be pricey, depending on the design.

  • Limited availability due to high demand.

Key Attractions and Events

  • Custom tattoos designed with you.

  • Art exhibits featuring local tattoo artists.

  • Professional and comfortable tattoo experience.

41. Take a Selfie with the ‘Welcome to Annapolis’ Sign

Short Description:
Capture a moment with the iconic ‘Welcome to Annapolis’ sign, which is a must-see for visitors to this beautiful historic city. Perfect for a fun and memorable photo, it symbolizes your arrival to a place rich in culture, history, and coastal beauty.

Pros and Cons:

  • Pros:

    • Great photo opportunity.

    • Easy to access for all visitors.

    • Popular spot for tourists.

  • Cons:

    • Can be crowded during peak tourist seasons.

    • Limited activities at the location aside from photos.

Key Attractions and Events:
This spot is a popular starting point for exploring the heart of Annapolis, with nearby attractions like City Dock and Main Street.

42. Experience the Annapolis Blues Soccer Match

Short Description:
Catch a live soccer match at the Maryland SoccerPlex with the Annapolis Blues, a semi-professional team offering high-energy matches that are perfect for sports fans of all ages.

Pros and Cons:

  • Pros:

    • Exciting live sports experience.

    • Family-friendly atmosphere.

    • Affordable ticket prices.

  • Cons:

    • Matches may be infrequent depending on the season.

    • Crowds can be large during big games.

Key Attractions and Events:
Watch the Annapolis Blues as they compete in their league and enjoy the energy of the crowd and the local sports scene.

43. Attend the Annapolis Arts Week

Short Description:
Annapolis Arts Week is an annual event that celebrates the rich cultural and artistic scene of the city. It features art exhibits, live performances, and cultural events that attract artists and art lovers from all over.

Pros and Cons:

  • Pros:

    • Great for art enthusiasts.

    • Variety of events across multiple venues.

    • Opportunity to interact with local artists.

  • Cons:

    • Events can be expensive depending on the venue.

    • Limited to certain times of the year.

Key Attractions and Events:
Artists’ exhibitions, gallery tours, outdoor art festivals, and live performances are highlights of the week.

44. Try Oyster Shooters at Boatyard Bar & Grill

Short Description:
Boatyard Bar & Grill is renowned for its fresh seafood, and their oyster shooters are a must-try. Savor the taste of local oysters served with cocktail sauce, making it a unique Annapolis experience.

Pros and Cons:

  • Pros:

    • Fresh, locally sourced oysters.

    • Fun and unique dining experience.

    • Casual, lively atmosphere.

  • Cons:

    • Not for everyone, especially those who don’t enjoy oysters.

    • Can be crowded during peak meal times.

Key Attractions and Events:
Boatyard Bar & Grill is also a popular spot for waterfront views, making it perfect for a relaxed evening meal or drink.

45. Bike the B&A Trail

Short Description:
The Baltimore & Annapolis (B&A) Trail is a scenic 13-mile pathway that runs from Baltimore to Annapolis. Ideal for cycling, jogging, or walking, it offers beautiful views of forests, streams, and open spaces.

Pros and Cons:

  • Pros:

    • Scenic and peaceful.

    • Suitable for all levels of cyclists.

    • Great way to enjoy the outdoors.

  • Cons:

    • Limited shade on some sections during hot weather.

    • Can be busy during weekends.

Key Attractions and Events:
Along the trail, you'll pass by parks, historic sites, and natural landmarks that make this an enjoyable outdoor activity.

46. See a Boat Parade (Especially at Christmas!)

Short Description:
Annapolis is known for its maritime culture, and the annual boat parade is a highlight, especially during the holiday season. Locals and visitors alike enjoy watching beautifully decorated boats glide by the waterfront.

Pros and Cons:

  • Pros:

    • Beautiful holiday tradition.

    • Family-friendly activity.

    • Free to watch from various spots along the water.

  • Cons:

    • Can be crowded, especially during the Christmas season.

    • Weather can affect visibility of the boats.

Key Attractions and Events:
The Christmas boat parade is a popular event, but boat parades are also held at other times of the year.

47. Do a Walking Tour with Historic Annapolis Foundation

Short Description:
Explore Annapolis’ rich history by taking a walking tour with the Historic Annapolis Foundation. You’ll learn about the city’s colonial past, notable buildings, and the stories that shaped this beautiful place.

Pros and Cons:

  • Pros:

    • Educational and immersive.

    • Expert guides offer detailed history.

    • Great for history buffs.

  • Cons:

    • Can be physically demanding with a lot of walking.

    • Limited availability during off-peak months.

Key Attractions and Events:
Historic buildings, such as the Maryland State House and St. Anne’s Church, are featured on the tours.

48. Visit the McBride Gallery

Short Description:
The McBride Gallery in Annapolis is an excellent spot for art lovers. Featuring works from local and regional artists, this gallery showcases a wide range of artistic styles, including contemporary and traditional art.

Pros and Cons:

  • Pros:

    • Features works from local talent.

    • Free entry for viewing.

    • A great opportunity to purchase unique artwork.

  • Cons:

    • Limited to art enthusiasts.

    • The gallery may not appeal to those not interested in art.

Key Attractions and Events:
Regular exhibitions, artist meet-and-greets, and special events bring the gallery to life.

49. Get Dessert at Annapolis Ice Cream Company

Short Description:
Treat yourself to some of the best ice cream in Annapolis at the Annapolis Ice Cream Company. With a variety of delicious flavors made from locally sourced ingredients, it’s the perfect place to cool off on a warm day.

Pros and Cons:

  • Pros:

    • Locally made, fresh ice cream.

    • Family-friendly.

    • Unique flavors.

  • Cons:

    • Can get crowded during peak summer months.

    • A bit on the pricier side.

Key Attractions and Events:
The Annapolis Ice Cream Company also participates in local festivals, making it a sweet spot to visit during events.

50. End the Day with Sunset at City Dock or Eastport Bridge

Short Description:
End your day with a peaceful sunset at one of Annapolis’ most picturesque spots. The City Dock offers stunning views over the harbor, while the Eastport Bridge gives a fantastic vantage point to capture the setting sun over the Chesapeake Bay.

Pros and Cons:

  • Pros:

    • Gorgeous views.

    • A relaxing way to end the day.

    • Excellent photo opportunities.

  • Cons:

    • Can get crowded, especially during summer.

    • Weather conditions can affect visibility.

Key Attractions and Events:
Both City Dock and the Eastport Bridge are close to other Annapolis landmarks, including local restaurants and shops, making it a great place to visit before heading out to dinner.

Best Time to Visit Annapolis

Annapolis is a year-round destination, each season offering its own unique charm. Whether you're looking for mild spring temperatures or festive winter vibes, there's always something to enjoy in Annapolis.

Season Highlights
Spring Mild temperatures, blooming gardens, and events like the Spring Sailboat Show.
Summer Warm weather perfect for sailing, waterfront dining, and festivals such as the Annapolis Arts Week.
Fall Crisp air, vibrant foliage, and events like the United States Sailboat Show.
Winter Festive holiday lights, indoor cultural events, and a cozy atmosphere in historic downtown.

Hidden Gems of Annapolis

Quiet Waters Park

For nature lovers, Quiet Waters Park is a serene 340-acre retreat offering wooded trails, art galleries, and picnic spots. Located just outside the city, it's the perfect spot for a peaceful day out, away from the hustle and bustle of downtown Annapolis.

Banneker-Douglass-Tubman Museum

Maryland’s official museum dedicated to African American history and culture is housed in a historic church. The Banneker-Douglass-Tubman Museum offers fascinating exhibits that showcase the state's rich African American heritage and provide a deeper understanding of Annapolis's historical significance.

Eastport Neighborhood

Just a short walk from downtown Annapolis, the Eastport neighborhood is a charming area known for its local eateries, breweries, and laid-back waterfront vibe. It's a great spot to enjoy a leisurely afternoon, sip craft beer, and savor fresh seafood.

Suggested Day Itinerary

Morning

  • Visit the U.S. Naval Academy: Start your day with a guided tour of the U.S. Naval Academy. This prestigious institution has shaped many of America's naval leaders, and its stunning campus offers a glimpse into the country's military history. The tour will walk you through the academy's rich traditions and notable landmarks.

  • Stroll Through the Historic District: After your tour, take a leisurely stroll through the Annapolis Historic District. Wander down Main Street, where you'll find beautiful Georgian buildings, charming boutiques, and quaint cafés. It's an ideal spot to soak up the city's colonial charm.

Afternoon

  • Lunch at a Waterfront Restaurant: Annapolis is renowned for its seafood, and there's no better place to enjoy fresh dishes than at a waterfront restaurant. Cantler's Riverside Inn and McGarvey's Saloon and Oyster Bar are two popular spots known for their delicious crab cakes and oysters.

  • Explore the William Paca House and Garden: After lunch, head over to the William Paca House and Garden, an 18th-century mansion with beautifully landscaped gardens. It's the perfect place to step back in time and explore Annapolis’s architectural beauty and history.

Evening

  • Sail on the Chesapeake Bay: As the sun begins to set, embark on a relaxing sailing tour around the Chesapeake Bay. The scenic views from the water are simply breathtaking, and it's the perfect way to unwind after a day of exploration.

  • Dine in Eastport: Wrap up your day with a meal in Eastport. This charming neighborhood is home to cozy restaurants like Forward Brewing, known for its craft beer and hearty dishes. It's the perfect spot to end your day with great food and a relaxed atmosphere.

How to Reach Annapolis

By Car

Annapolis is easily accessible by car, just a 45-minute drive from Washington, D.C., via U.S. Route 50 East. The city is well-connected, and its proximity to major cities makes it a convenient destination.

By Public Transit

The Maryland Transit Administration (MTA) operates bus services that connect Annapolis with nearby cities, including Baltimore and Washington, D.C. This makes it easy for visitors to reach the city without the need for a car.

By Air

The nearest major airport to Annapolis is Baltimore/Washington International Thurgood Marshall Airport (BWI), located about 30 minutes away by car. There are also smaller regional airports nearby, but BWI is the most convenient for travelers flying in from other states.

Conclusion

Annapolis, Maryland, offers a delightful mix of historical charm, cultural richness, and maritime adventures. Whether you're exploring its colonial landmarks, indulging in fresh seafood, or sailing on the Chesapeake Bay, Annapolis ensures an unforgettable experience for every traveler. This city beautifully blends the past with the present, offering something for everyone, from history enthusiasts to foodies and outdoor adventurers.

Frequently Asked Questions (FAQs)

Q1: What is the best time to visit Annapolis?

Annapolis is a year-round destination. Spring and fall offer mild temperatures and fewer crowds, while summer is ideal for sailing and waterfront activities. Winter brings festive holiday events and a cozy atmosphere.

Q2: How can I get around Annapolis without a car?

Annapolis is a walkable city, especially downtown. Public buses and water taxis are available for longer distances or waterfront travel.

Q3: Are there family-friendly activities in Annapolis?

Absolutely. Families can enjoy the U.S. Naval Academy tour, interactive exhibits at local museums, and sailing excursions suitable for all ages.

Q4: Where can I experience local cuisine in Annapolis?

The city boasts numerous restaurants offering Maryland specialties, particularly fresh seafood like crab cakes and oysters. Popular spots include Cantler's Riverside Inn and The Point.

Q5: Is Annapolis a good destination for history enthusiasts?

Yes, Annapolis is rich in history, featuring sites like the Maryland State House, the William Paca House, and the Banneker-Douglass-Tubman Museum.

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