Key Takeaways:
- Annapolis, Maryland is a charming city known for its rich history, stunning waterfront, and vibrant cultural scene.
- From exploring historic landmarks to enjoying outdoor activities, Annapolis offers something for everyone throughout the year.
- Whether you’re a history buff, a sailing enthusiast, or a foodie, Annapolis provides year-round entertainment and activities.
Table of Contents
- Visit the United States Naval Academy
- Stroll Through Historic Annapolis Downtown
- Tour the Maryland State House
- Enjoy the Annapolis Waterfront
- Explore Quiet Waters Park
- Take a Sailing Tour on the Chesapeake Bay
- Visit the Banneker-Douglass Museum
- Attend the Annapolis Film Festival
- Enjoy Live Music at Rams Head Tavern
- Walk Along the Capital Crescent Trail
Annapolis, the capital of Maryland, is a beautiful city brimming with history, culture, and scenic views. Situated along the Chesapeake Bay, the city has long been a hub for maritime history and political importance. Annapolis is home to the United States Naval Academy, iconic landmarks like the Maryland State House, and a charming historic district filled with cobblestone streets and colonial-era architecture. Whether you’re visiting for a day or planning a longer stay, Annapolis offers a variety of attractions and activities that captivate visitors year-round. From outdoor adventures to cultural experiences, Annapolis is a perfect destination for all types of travelers.
1. Visit the United States Naval Academy
The United States Naval Academy in Annapolis is one of the nation’s most prestigious institutions, and visiting its campus is a must for anyone traveling to the city. The Academy offers guided tours where you can learn about the history of the institution, see its beautiful architecture, and visit famous sites like the Memorial Hall and the Bancroft Hall. The academy is steeped in tradition, and the tour offers insight into the lives of midshipmen and the role the academy has played in shaping U.S. naval history. It’s an incredible experience for anyone interested in military history and education.
In addition to the guided tours, visitors can explore the stunning grounds and enjoy scenic views of the Severn River and Annapolis Harbor. The campus itself is a blend of historic buildings and modern facilities, providing a unique look into the tradition and evolution of the U.S. Navy. Whether you’re a history enthusiast or simply looking to explore an iconic landmark, the United States Naval Academy is a must-see destination. (You can learn more about this by visiting U.S. Naval Academy website)
2. Stroll Through Historic Annapolis Downtown
Annapolis’s downtown area is a charming and historic district filled with narrow streets, colonial architecture, and waterfront views. The area is a National Historic Landmark, with buildings dating back to the 18th century. Visitors can take a leisurely stroll through the downtown district, popping into local shops, cafés, and restaurants along the way. Historic sites like the Hammond-Harwood House and the William Paca House provide a glimpse into Annapolis’s rich past, making it a fantastic area to explore on foot.
Downtown Annapolis is also home to the iconic City Dock, where you can enjoy views of the harbor, watch sailboats and ships, and enjoy the vibrant atmosphere. With its mix of history, culture, and local businesses, Annapolis’s downtown is a must-visit for anyone in the area. Whether you’re looking to shop, dine, or learn about the city’s history, the historic downtown area has something to offer everyone. (You can learn more about this by visiting Historic Annapolis website)
3. Tour the Maryland State House
The Maryland State House is the oldest state capitol in continuous use and a must-see landmark in Annapolis. This beautiful building, with its striking dome and historic architecture, has served as the site of many important events in American history, including the signing of the Treaty of Paris that ended the Revolutionary War. Visitors can take guided tours of the State House to learn about its history and explore its beautiful chambers, including the Senate and House of Delegates. The tour provides a fascinating look into the political history of Maryland and the nation.
In addition to its political history, the Maryland State House is an architectural marvel, offering stunning views from its grounds. The surrounding area also features lovely gardens and is a great place to take a stroll while enjoying the history and beauty of the site. If you’re interested in history and government, the Maryland State House is a key stop when visiting Annapolis. (You can learn more about this by visiting Maryland State House website)
4. Enjoy the Annapolis Waterfront
The Annapolis Waterfront is one of the city’s most scenic spots, offering beautiful views of the harbor and a variety of waterfront activities. Whether you’re enjoying a meal at one of the waterfront restaurants or simply strolling along the docks, the area provides a relaxing environment with stunning water views. The harbor is also home to many sailboats, yachts, and ships, giving it a vibrant maritime atmosphere. If you’re lucky, you might catch sight of a tall ship or one of the many boat races held in the harbor throughout the year.
For those interested in boating or sailing, there are numerous opportunities to rent a boat, take a sailing tour, or learn how to sail. The waterfront is an ideal spot for anyone looking to relax by the water or enjoy a maritime adventure. With its beautiful views and nautical charm, the Annapolis Waterfront is a must-see during your visit. (You can learn more about this by visiting Annapolis Waterfront website)
5. Explore Quiet Waters Park
Quiet Waters Park is a peaceful and scenic park located just outside Annapolis, offering visitors a serene escape into nature. The park features several walking trails that wind through woodlands and wetlands, providing a perfect spot for hiking and wildlife viewing. The park is also home to the Quiet Waters Sculpture Garden, where visitors can view a variety of outdoor sculptures set against the backdrop of the natural surroundings. Whether you’re looking for a peaceful place to walk, relax, or enjoy art, Quiet Waters Park offers a wonderful blend of nature and creativity.
In addition to its trails and sculpture garden, the park hosts various art exhibits, workshops, and community events, making it a lively cultural space. The park’s tranquil atmosphere makes it a great place to unwind, have a picnic, or simply enjoy the beauty of nature. Quiet Waters Park offers an ideal way to spend time outdoors while exploring the artistic and natural wonders of Annapolis. (You can learn more about this by visiting Quiet Waters Park website)
6. Take a Sailing Tour on the Chesapeake Bay
Annapolis, often referred to as the sailing capital of the U.S., offers numerous opportunities for visitors to take a sailing tour on the iconic Chesapeake Bay. There are several companies offering private and group tours, allowing you to experience the bay’s stunning views, abundant wildlife, and the thrill of being on the water. Whether you’re an experienced sailor or a first-time visitor, these tours provide a fantastic way to explore the bay and learn about its history and ecology. The tour guides often share interesting facts about the area’s maritime culture, making it an educational experience as well as an enjoyable one.
Sailing on the Chesapeake Bay offers the perfect opportunity to disconnect from everyday life and immerse yourself in the beauty of the water. Whether you’re looking for a romantic sunset cruise or a family-friendly tour, Annapolis offers plenty of options for every type of adventurer. The views, the breeze, and the calm waters make this one of the most memorable activities in Annapolis. (You can learn more about this by visiting Chesapeake Bay Sailing Tours website)
7. Visit the Banneker-Douglass Museum
The Banneker-Douglass Museum is Maryland’s official museum of African American heritage and culture. Located in Annapolis, this museum celebrates the history and achievements of African Americans in Maryland, showcasing a wide range of exhibits and programs that highlight their contributions to society. Visitors can explore exhibits that focus on prominent figures like Benjamin Banneker, an African American scientist and surveyor, and Frederick Douglass, an abolitionist and writer. The museum also provides insight into the African American experience, from slavery to civil rights, making it a vital cultural landmark in Annapolis.
In addition to its permanent exhibits, the Banneker-Douglass Museum hosts events, workshops, and educational programs throughout the year. It’s an excellent place to visit for anyone interested in learning more about African American history and culture. Whether you’re a history enthusiast or just looking to explore Maryland’s diverse past, the Banneker-Douglass Museum is a must-visit destination. (You can learn more about this by visiting Banneker-Douglass Museum website)
8. Attend the Annapolis Film Festival
The Annapolis Film Festival is an annual event that attracts film lovers and industry professionals from all over the world. Held every spring, the festival showcases a diverse selection of independent films, including documentaries, shorts, and feature-length movies. It’s an excellent opportunity to experience the work of talented filmmakers and see films that may not be available in mainstream theaters. The festival also features panels, Q&A sessions with filmmakers, and networking events, making it a vibrant and engaging cultural event in the city.
The Annapolis Film Festival is a great way to experience the arts in a lively and community-oriented setting. Whether you’re attending screenings, engaging with filmmakers, or simply enjoying the atmosphere, the festival offers something for everyone. If you’re a movie buff or simply looking for a unique cultural experience, the Annapolis Film Festival is a fantastic event to check out. (You can learn more about this by visiting Annapolis Film Festival website)
9. Enjoy Live Music at Rams Head Tavern
Rams Head Tavern is a well-known venue in Annapolis that offers a great selection of live music performances, from local bands to touring acts. The tavern’s intimate setting allows for an up-close-and-personal experience with your favorite musicians. Whether you’re into rock, jazz, blues, or acoustic, Rams Head Tavern hosts a wide variety of performances that cater to different tastes. The venue’s relaxed atmosphere and great acoustics make it a top spot for enjoying live music in Annapolis.
In addition to live music, Rams Head Tavern also serves a delicious menu of food and drinks, making it a great place to enjoy a meal while taking in a show. Whether you’re planning a night out with friends or looking for a fun date night spot, Rams Head Tavern offers an unforgettable live music experience. It’s one of the best places in Annapolis to catch live performances and enjoy a fun evening. (You can learn more about this by visiting Rams Head Tavern website)
10. Walk Along the Capital Crescent Trail
The Capital Crescent Trail is a scenic, 11-mile-long trail that stretches from downtown Bethesda, Maryland, to Silver Spring, passing through beautiful landscapes and historic sites. While it extends outside Annapolis, it’s a popular spot for visitors from Annapolis who enjoy outdoor activities like biking, walking, and running. The trail winds through forested areas, along rivers, and past urban landscapes, offering a peaceful and enjoyable way to explore the region. Whether you’re walking for fitness or simply to take in the scenery, the Capital Crescent Trail is a wonderful way to spend a few hours in nature.
Along the trail, you’ll find plenty of opportunities for wildlife spotting, photography, and enjoying the tranquility of the surroundings. It’s an ideal activity for those who want to escape into nature without venturing too far from the city. The Capital Crescent Trail is also perfect for families and outdoor enthusiasts, offering a great way to enjoy the outdoors year-round. (You can learn more about this by visiting Capital Crescent Trail website)
What to do if you have kids?
Annapolis is a fantastic destination for families, offering a wide range of activities for kids. For an outdoor adventure, take the kids to Quiet Waters Park, where they can explore nature trails and learn about local wildlife. The Banneker-Douglass Museum offers educational programs that will engage children with African American history, while Rams Head Tavern features family-friendly live music events. Annapolis also has several parks and the Chesapeake Bay for family-friendly boating or fishing excursions. No matter what your kids are into, Annapolis offers plenty of fun and educational experiences for families.
Where can I find free events in Annapolis, Maryland taking place this weekend?
To find free events happening in Annapolis this weekend, check out Planmyweekend.ai. This tool helps you find free local events, including outdoor festivals, concerts, and family activities based on your location and the date. Whether you’re interested in arts, history, or outdoor adventures, Planmyweekend.ai provides an easy way to discover the best free events happening in Annapolis.
Final Thoughts
Annapolis, Maryland, is a beautiful city offering a perfect mix of history, culture, and natural beauty. Whether you’re visiting for the historic sites, enjoying a day on the Chesapeake Bay, or attending a local festival, Annapolis offers something for every type of traveler. From family-friendly activities to cultural experiences, Annapolis has it all year-round. Be sure to use Planmyweekend.ai to find free events and make the most of your time in this charming city.
Author: Dejon Brooks
Dejon Brooks is an entrepreneur who founded Trend Watchers with his life savings. Aged 24, Dejon has turned Trend Watchers into a successful business. After reaching over 150M+ people on his personal accounts, he now spends his time growing Planmyweekend.ai
