Annapolis, Maryland: Best Things to Do – Top Picks

A picturesque cityscape of Annapolis, Maryland on a sunny day. In the foreground, charming colonial-style buildings line the cobblestone streets, their red brick and white trim gleaming in the warm light. In the middle ground, the historic Maryland State House and St. Anne's Church stand tall, their steeples casting shadows across the scene. Beyond, the sparkling waters of the Severn River and Chesapeake Bay stretch out, framed by the lush, verdant trees lining the shore. The sky is a brilliant blue, dotted with fluffy white clouds, creating a tranquil and inviting atmosphere. Capture the essence of Annapolis' picturesque charm and historic significance through a meticulously detailed, realistic cityscape.

As one of America’s oldest historic cities, Annapolis exudes charm through its rich colonial history and picturesque waterfront setting on the Chesapeake Bay.

Visitors from around the world are drawn to this captivating city for its unique blend of historical attractions, maritime activities, and cultural experiences.

With its storied past and modern amenities, Annapolis creates an unforgettable experience for those who visit. From its significance as the former capital of the United States to its reputation as “America’s Sailing Capital,” there’s much to explore in this charming city.

Discovering Annapolis: Maryland’s Historic Capital

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Discover the allure of Annapolis, a city steeped in colonial history and architectural beauty. As one of the oldest cities in the United States, Annapolis served as the nation’s capital before the District of Columbia took over this role.

At the heart of downtown Annapolis lies a beautifully preserved area filled with brick-lined streets and colorful colonial-era buildings. This historic town is perfect for a self-guided walking tour, allowing you to explore its many landmarks.

  • Immerse yourself in the rich colonial atmosphere of Annapolis.
  • Understand why Annapolis holds such historical significance.
  • Explore the heart of downtown Annapolis.
  • Learn about the city’s designation as a National Historic Landmark District.
  • Discover how the town’s strategic location shaped its development.
  • Find out how to navigate the historic district.
  • Appreciate the architectural beauty that spans several centuries.

Explore the U.S. Naval Academy

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As you explore Annapolis, a visit to the United States Naval Academy is an unforgettable experience. Founded by George Bancroft in 1845, this prestigious institution is home to thousands of midshipmen training to become officers in the U.S. Navy and second lieutenants in the Marine Corps.

The Naval Academy’s campus, known as “The Yard,” is filled with historic monuments and Beaux-Arts architecture. Visitors can take a guided tour of The Yard, either on foot or by using a five-passenger electric vehicle.

Some highlights of your visit include the Naval Academy Museum at Preble Hall, which features two floors of exhibits on the history of seapower and the U.S. Navy. You can also marvel at the magnificent Naval Academy Chapel, with its striking dome visible throughout Annapolis.

As you learn about the rigorous training and traditions that shape the midshipmen, you’ll appreciate the legacy that dates back to George Washington’s vision for a naval service. Don’t forget to understand the security procedures for visitors, including showing valid ID at the visitor center before entering this active military installation.

Visit the Maryland State House

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As you explore Annapolis, a visit to the Maryland State House is a must, given its historical significance. Completed in 1779, it is the oldest state house still in continuous use by the legislature. The building served as the capital of the fledgling United States of America and was the meeting place of the Continental Congress from November 1783 to August 1784.

During its time as the nation’s capital, significant events took place within its walls, including the ratification of the Treaty of Paris, which officially ended the Revolutionary War, and George Washington’s resignation as General of the Continental Army, establishing civilian control of the military.

You can explore the historic Old Senate Chamber, marvel at the distinctive wooden dome constructed without nails, and learn about Maryland’s political history through various chambers and exhibits. The State House blends original 18th-century architecture with early 20th-century additions, preserving its historical integrity.

Stroll Through Historic Downtown Annapolis

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Historic Downtown Annapolis is a treasure trove of history, culture, and entertainment. As you wander through the charming brick-lined streets, you’ll discover a blend of colonial architecture and modern amenities.

Start your exploration on Main Street, the vibrant heart of the city, where colorful storefronts housed in 18th and 19th-century buildings offer a unique shopping experience. You’ll find a variety of unique boutiques, art galleries, and specialty shops offering everything from maritime-themed souvenirs to upscale fashion and home décor.

  • Wander through the charming brick-lined streets of historic downtown Annapolis.
  • Explore Main Street, lined with colorful storefronts in historic buildings.
  • Discover unique shops, art galleries, and specialty stores.
  • Sample the diverse dining scene, from casual seafood to upscale restaurants.
  • Take in the lively atmosphere, especially during weekend evenings and seasonal festivals.
  • Find hidden gems in side streets and alleyways.
  • Appreciate the preservation of historic character in this walkable downtown area.

As you stroll through this historic area, you’ll spot a mix of old and new, creating a unique and memorable experience. Whether you’re looking for things to do or just want to enjoy the city atmosphere, downtown Annapolis has something for everyone.

Experience City Dock and Ego Alley

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For centuries, City Dock has been the maritime soul of Annapolis, attracting visitors with its rich history and vibrant atmosphere. As you stroll along the dock, you’ll be surrounded by bay-side restaurants and shops, offering a blend of fresh seafood and maritime-themed gifts.

One of the highlights of City Dock is Ego Alley, a narrow waterway where boat owners proudly display their impressive yachts and sailboats. You can watch the parade of vessels and enjoy the lively atmosphere that makes City Dock a favorite spot for both locals and visitors.

With its strategic location in downtown Annapolis, City Dock is also a hub for boat tours, offering unique perspectives of the city from the water. Whether you’re interested in history, dining, or simply enjoying the views, City Dock is a must-visit destination.

Tour Historic Homes and Gardens

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Step into the past by visiting the grand historic homes and gardens that dot the landscape of Annapolis. One of the most notable is the William Paca House, an immaculately restored 18th-century Georgian mansion.

This grand colonial-era home was completed in 1765 for William Paca, a wealthy young planter who was a signer of the Declaration of Independence and Governor of Maryland. After years of neglect, the home was painstakingly restored, and its gardens were meticulously reconstructed from old photographs.

Today, the William Paca House boasts one of the loveliest gardens in Annapolis, covering two acres with five terraces featuring authentic flora, including topiaries, a medicinal herb garden, and water gardens. You can also visit other notable historic homes, such as the Hammond-Harwood House, known for its perfect proportions and exquisite woodwork.

Guided tours of these homes provide insight into colonial life and early American architecture, highlighting original furnishings and period décor. You’ll discover how these properties were saved from destruction and restored to preserve Annapolis’s architectural heritage.

Annapolis, Maryland: Best Things to Do – Top Picks for Maritime Enthusiasts

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With its rich maritime history and stunning Chesapeake Bay views, Annapolis is a must-visit destination for maritime enthusiasts. The city’s deep connection to the bay is evident in its maritime culture, historic sailing vessels, and exciting sailing experiences.

Annapolis Maritime Museum

The Annapolis Maritime Museum is a treasure trove of maritime history, located on the shores of Back Creek in the last oyster packing plant to operate in Annapolis. The museum showcases the city’s seafaring heritage through a collection of artifacts and documents, and features an 850-gallon aquarium that teaches visitors about the ecosystem of an oyster reef.

Schooner Woodwind Sailing Cruises

Experience the thrill of sailing on the Schooner Woodwind, a 74-foot wooden sailboat that offers daily cruises from the Annapolis waterfront. As you sail, you’ll enjoy breathtaking views of the Naval Academy, Bay Bridge, and historic skyline. You can choose from various cruise options, including sunset sails, Wednesday night races, and special themed excursions featuring local beer tastings or live music.

Annapolis is known as “America’s Sailing Capital,” and for good reason. The city’s maritime experiences showcase its deep connection to the Chesapeake Bay, from boat building traditions to the oyster industry. Whether you’re a seasoned sailor or just looking for a relaxing cruise, Annapolis has something for everyone.

Explore African-American Heritage Sites

Annapolis, Maryland: Best Things to Do - Top Picks

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Delve into the profound history of African Americans in Annapolis by visiting its significant heritage sites. Annapolis is a city with a rich and complex history, and its African-American heritage is a vital part of that narrative.

Banneker-Douglass Museum

The Banneker-Douglass Museum is the state’s official Museum of African American Heritage, located in a historic church known as Mt. Moriah African Methodist Episcopal Church. Here, you can explore the permanent exhibit, “Deep Roots, Rising Waters: A Celebration of African Americans in Maryland,” along with temporary exhibits that showcase the struggles and achievements of African Americans.

Kunta Kinte-Alex Haley Memorial

Located in City Dock, the Kunta Kinte-Alex Haley Memorial pays tribute to Alex Haley and his ancestor, Kunta Kinte, who was brought to America on a slave ship in 1767. The memorial includes bronze sculptures and a series of plaques along the seawall known as the “Story Wall,” making it a powerful tribute to the history of African Americans in Annapolis.

By visiting these sites, you’ll gain a deeper understanding of the significant role African Americans played in shaping Annapolis’s history and culture. The city’s heritage sites offer a unique glimpse into the past, highlighting the struggles, achievements, and contributions of African Americans from the colonial era to the present day.

Enjoy Outdoor Recreation in Annapolis

Discover the great outdoors in Annapolis, where nature and adventure await. You can escape the historic district and experience the natural beauty surrounding Annapolis with outdoor activities for all ages and interests.

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Quiet Waters Park

Explore Quiet Waters Park, a 340-acre oasis featuring six miles of paved trails, formal gardens, a dog beach, and stunning views of the South River. You can rent kayaks, canoes, or paddleboards to explore the peaceful waterways.

Sandy Point State Park

Visit Sandy Point State Park, located at the western end of the Chesapeake Bay Bridge, offering panoramic views of the bay and a mile-long beach perfect for swimming and sunbathing. Try fishing, crabbing, or boating, and watch massive ships entering and leaving the Port of Baltimore.

Shop and Dine on Main Street

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Annapolis’s Main Street is a vibrant destination that combines historic allure with modern shopping and dining delights. As you stroll along this charming street, you’ll discover a variety of unique boutiques and art galleries showcasing local artwork and nautical-themed gifts.

The culinary scene on Main Street is equally impressive, with a diverse range of restaurants serving fresh food from the Chesapeake region, including blue crabs and oysters. You can enjoy these local specialties in historic buildings that have been part of the community for centuries.

Whether you’re a visitor or a local, Main Street offers an eclectic mix of dining and entertainment options, from casual bars to fine dining establishments. Come and experience the heart of Annapolis.

Take a Guided Tour of Annapolis

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To truly experience Annapolis, consider taking one of the many guided tours that showcase its historic significance and architectural beauty. Guided tours offer a wealth of knowledge about the city’s rich history, landmarks, and cultural heritage.

Walking Tours

Join a walking tour led by knowledgeable local guides who bring the stories of colonial Annapolis to life as you stroll through the historic district. You’ll learn about architectural styles, famous residents, and the political intrigue that shaped this important early American city.

Trolley and Boat Tours

For a more comprehensive overview, hop aboard a trolley tour that covers more ground while you enjoy the comfort of a climate-controlled vehicle. Alternatively, experience Annapolis from the water with a boat cruise that offers unique perspectives of the city skyline, Naval Academy, and waterfront mansions.

Choose from specialized tours focusing on specific themes like colonial history, maritime heritage, or the African-American experience in Annapolis. With expert guides providing insights and answering questions, you’ll gain a deeper understanding of this historic city.

Unique Annapolis Experiences

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Beyond the standard tourist attractions, Annapolis has a lot to offer for those seeking distinctive experiences. Whether you’re interested in the paranormal, local cuisine, or maritime events, Annapolis caters to a wide range of interests.

Ghost Tours

Annapolis is renowned for its ghost tours, which delve into the city’s dark history and haunted sites. With Tours & Crawls, you can embark on a 90-minute walking tour or join a haunted pub crawl, visiting 3-4 haunted bars and sampling local spirits while listening to spine-tingling tales.

Local Food Specialties

When you visit Annapolis, be sure to indulge in the local food scene, particularly the region’s famous blue crabs seasoned with Old Bay. You can enjoy them steamed whole or in the form of Maryland’s signature crab cakes. Exploring the local craft beverage scene by visiting area breweries, wineries, and distilleries is also a must.

Annapolis Boat Shows

Annapolis hosts prestigious boat shows, including the United States Sailboat Show and Powerboat Show, transforming the harbor into the largest in-water boat show in the world. These events showcase a variety of boats and offer a unique experience for maritime enthusiasts.

Planning Your Visit to Annapolis

As you plan your trip to Annapolis, Maryland, you’ll discover a city rich in history, maritime culture, and natural beauty. To make the most of your visit to Annapolis, consider the best times to go; spring and fall offer pleasant weather and fewer crowds, while summer brings vibrant waterfront activities.

Start your exploration at the Visit Annapolis Visitors Center on West Street, where you can get maps, brochures, and personalized recommendations. Allocate at least two to three days to experience the essential things Annapolis has to offer, including its historic sites and culinary scene. Be prepared for walking on brick and cobblestone streets by wearing comfortable shoes, and check the Visit Annapolis website for current events happening during your visit.

By planning ahead, you’ll ensure a memorable trip to this charming city. With so much to see and do, visitors are sure to leave with unforgettable memories. So, plan your trip today and get ready to enjoy all that Annapolis has to offer.

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