Spending your weekends in Annapolis? You’re in for a treat. This waterfront city has everything your mind and body could want—history, adventure, and incredible food that keep tourists coming back and locals out exploring for hours. It doesn’t matter if you want to sail the bay, eat your weight in crab cakes, or stroll through streets that look straight out of a history book—there’s something for everyone. With so many fun things to do in Annapolis on weekends, you’ll never run out of ways to explore and enjoy the city. If you decide to move here, you’ll want to jump into the action right away. That’s where A2B Moving and Storage comes in—because the sooner your stuff is delivered and unpacked, the sooner you’re out there enjoying everything Annapolis has to offer.
Explore the outdoors with water activities and scenic parks
Sailing and boating adventures on the Chesapeake Bay
When you think of sailing in the U.S., the first thought that comes through your head is Annapolis; that is exactly why the city holds the title of “Sailing Capital of the U.S.” Because of that title, the city has many sailing tours to offer, and the first one should be the boat tour on the Chesapeake Bay; it is a must-see for any visitor. Outside of that, there are other options such as the Schooner Woodwind and the Annapolis Water Taxi, both of which give you a unique perspective of the city. You are also free to rent a sailboat and captain your own trip along the bay. Exploring the bay by boat is one of the most fun things to do in Annapolis on weekends; that goes even more when the weather is warm and sunny.
Parks, trails, and waterfront recreation
If you love being active on the water, Annapolis offers kayaking and paddleboarding. One great place is Quiet Waters Park; it offers both rentals and easy water access. The park also has some of the most scenic hiking trails, picnic spots, and an ice-skating rink in the winter. Another park that is often neglected by tourists is Jonas Green Park, which is terrible as it offers great fishing areas, walking paths, and stunning vistas overlooking the Severn River.
Discover nature and hands-on learning experiences
And if you are a bit of a nature geek, you might want to explore the Annapolis Maritime Museum & Park. They offer some hands-on exhibits that are out of this world. The museum highlights the history of Chesapeake Bay, and its scenic trails make for a relaxing weekend outing. You are also free to join some community events that are often an attraction there for both locals and visitors alike.
For those moving into the area, movers Annapolis MD locals trust provide professional relocation services, helping new residents get settled so they can start enjoying these outdoor activities.
Visit historic sites and step back in time
If a city could be called a “blast in the past,” then it would be Annapolis. It’s one of the most historically significant cities in the U.S. One of its main attractions would be the Maryland State House, which is from 1772 and thus provides a great view into the era of the American Revolution. Then this building was the U.S. Capitol and the home of George Washington, who resigned his commission as commander of the Continental Army in this building. Visitors could also choose to tour the State House and see the original documents from the Revolutionary Era. And those who want to learn about the Maryland State House can explore its connection to key moments in American history, from the Treaty of Paris to its role in early government meetings.
Founded in 1692, St. Anne’s Church is the oldest church in Annapolis. It has a lot to offer for both locals, tourists, and churchgoers. The church features beautiful stained glass and a peaceful courtyard. And if you are more of a tour person, you are free to choose that option as well, as it offers great insight into its role in the city’s past.
For you walkers out there, downtown Annapolis is the place to go. The area is lined with historic streets and homes, imbuing the city with a feel of being centuries old, and it is a unique feel you won’t find anywhere else. The William Paca House & Garden is a lovely, restored 18th-century mansion that has been brought back to its old colonial life. It’s absolutely worth seeing in spring (and summer—the gardens are teeming with native flora and tucked-away paths).
Those interested in African American history can visit the Banneker-Douglass Museum, which highlights the contributions of Black Marylanders. From exhibits on Frederick Douglass to artwork by local creators, the museum provides a powerful experience.
Enjoy fresh seafood and lively food spots
No weekend in Annapolis is complete without some of its famed seafood. Some of the best Maryland crab in the state is served at local restaurants. The Boatyard Bar & Grill, a popular place for crab cakes and oysters, is near the harbor. Cantler’s Riverside Inn is another famous seafood restaurant, where customers crack open steamed blue crabs on the water’s edge.
For a relaxed vibe, Davis’ Pub serves seafood and comfort food. Locals adore its crab pretzels, Old Bay wings, and easygoing vibe. Also nearby, the Market House, a historic food hall overlooking the waterfront, is an excellent place for a quick bite.
The city’s brewery scene is also growing, with spots like Forward Brewing and Chesepiooc Real Ale Brewery serving unique local beers. These breweries offer a rotating selection of craft beers, with outdoor seating perfect for a relaxed weekend. Many also host trivia nights, live music, and food truck events.
Annapolis Farmers Market is another popular stop for food lovers. Every weekend, vendors sell fresh produce, homemade jams, baked goods, and artisan crafts. The market is a great place to find local specialties and enjoy a leisurely morning.
For new residents, a well-organized move with moving services DC residents adore ensures they have time to explore these great food spots instead of dealing with moving stress.
Experience live music, museums, and family fun
Annapolis has a vibrant arts and entertainment scene. Some of the top places to experience live music include Rams Head On Stage. This small venue features national acts and local musicians. There are enough performances, from rock to folk, that everyone can find something they’ll see and enjoy.
And, for museum lovers, the U.S. Naval Academy Museum provides an intriguing view of military history. The museum has models of ships, historic uniforms, and many artifacts from battles at sea. For those seeking greater knowledge of the Navy’s role in American history, it’s a must visit.
Families can take advantage of Annapolis’s many parks, which often host outdoor movie nights, festivals, and live performances. Quiet Waters Park and Truxtun Park frequently have family-friendly activities, making them of the better fun things to do in Annapolis on weekends. The Chesapeake Children’s Museum is another excellent place for kids, offering hands-on exhibits and nature trails.
Make the most of weekends as a new resident
Moving to a new city can feel overwhelming, but joining local groups and planning weekend outings can help new residents feel at home. Annapolis has several organizations that host meetups for new arrivals, including sailing clubs, walking groups, and community volunteer programs. Getting involved is one of the best ways to discover all the fun things to do in Annapolis on weekends while meeting new people.
To fully enjoy weekends in Annapolis, consider:
- Joining social clubs – Meet locals through sailing, hiking, or historical walking tours.
- Exploring nearby cities – Baltimore and Washington, D.C., are both less than an hour away.
- Visiting Sandy Point State Park – Relax on the beach and enjoy the scenic Chesapeake Bay.
- Taking a weekend winery tour – Try local wines at vineyards in the surrounding countryside.
- Checking out seasonal events – Farmers markets, festivals, and outdoor concerts happen year-round.
By choosing reliable moving companies Maryland residents love, new arrivals can focus on exploring instead of unpacking. A well-planned move means more time to enjoy Annapolis’s best activities.
Embrace the Annapolis lifestyle and enjoy every weekend
Annapolis is a city full of exciting activities, from waterfront adventures to historic sites. Spending weekends exploring local events and new places helps create lasting memories. Whether it’s live music, fresh seafood, or sailing, there are always fun things to do in Annapolis on weekends!
